ChemWiki - User contributions [en]

It07:DIBAL

2007-12-05T11:46:54Z

Zh206: /* DIBAL Di-IsoButyl Aluminium Hydride */

=DIBAL Di-IsoButyl Aluminium Hydride=
[[Image:DIBAL1.png]]

<jmol>
<jmolApplet>
<title>DIBAL</title><color>yellow</color>
<size>200</size>
<script>zoom 80; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>DIBAL10.mol</uploadedFileContents>
</jmolApplet>

<jmolMenu>
<item><text>Start spinning</text><script>spin on</script></item>
<item><text>Stop spinning</text><script>spin off</script></item>
<menuHeight>-1</menuHeight>
</jmolMenu>
<jmolButton>
<script>console</script>
<text>open a console window</text>
</jmolButton>
</jmol>

<jmol>
<jmolAppletButton>
<title>Show DIBAL in popup window</title>
<color>cyan</color>
<uploadedFileContents>DIBAL10.mol</uploadedFileContents>
</jmolAppletButton>
</jmol>

<noinclude>

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | {{PAGENAME}} 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:DIBAL1.png|200px|{{PAGENAME}}]] 
|-
! {{chembox header}} | General
|-
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]
| Di-Isobutyl Aluminium Hydride

|-
| Other names
| DIBAL, DIBAL-H, DIBAH, DIBALH
|-
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| [(CH<sub>3</sub>)<sub>2</sub>CHCH<sub>2</sub>]<sub>2</sub>AlH
|-
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] 
| [H][Al]CC(C)C.CCC(C)C
|-
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| 142.22
|-
| Appearance
| Clear, colourless liquid
|-
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| 1191-15-7
|-
! {{chembox header}} | Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] & [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]
| 0.798 g/cm³ 
|-



| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| 255.15 K 
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| 389.15-391.15 K
|-
! {{chembox header}} | Hazards 
|-
| [[Material safety data sheet|MSDS]]
| [[{{PAGENAME}} (data page)#Material Safety Data Sheet|External MSDS]] 
|-
| Main [[Worker safety and health|hazard]]s
| Corrosive, highly flammable. 
|-
|-
|-
|-
|-

|-
|-
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic<br />data]]
| Liquid
|-
|-
! {{chembox header}} | 3-D Structure
|-
|-
|3D
|<jmol>
<jmolApplet>
<title>DIBAL</title><color>yellow</color>
<size>250</size>
<script>zoom 120; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>DIBAL.mol</uploadedFileContents>
</jmolApplet>
<jmolMenu>
<item><text>Start spinning</text><script>spin on</script></item>
<item><text>Stop spinning</text><script>spin off</script></item>
<menuHeight>-1</menuHeight>
</jmolMenu>
</jmol>
|-
|-
|-
|-
|-
|-
|}

==Introduction==

<ref>http://www.akzonobel-polymerchemicals.com/NR/rdonlyres/CB29DA1C-1144-47F4-888A-B20FC61E17F5/11037/Diisobutylaluminumhydride_ma_row_eng_tb.pdf</ref>
DIBAL has rapidly established itself as a reducing agent of choice in organic synthesis. It is most effective at reducing electron-rich carbonyl groups and has largely replaced the use of metal hydrides (including LiAlH<sub>4</sub> and NaBH<sub>4</sub>) due to economic advantages. It demonstrates increased selectivity and a considerably lower cost per reducing equivalent. It is also a particularly easy-handling material as it is a liquid that is miscible in many solvents.
DIBAL exists as a dimer due to increased stabilisation:
[[Image:DIBAL6.png]]

==Reduction of Esters to Aldehydes using DIBAL==

Chemists often come across a problem when reducing an ester to an aldehyde. This is because the aldehyde product is more susceptible to reduction than the starting ester and therefore the reduction process continues to the next oxidation level – to the alcohol.
DIBAL, however, can be used as a reagent that will carry out this reduction in 1 step and stops at the aldehyde without further reduction.

[[Image:Ester3.png]]

<ref>“ORGANIC CHEMISTRY” Clayden, Greeves, Warren & Wothers</ref>

At -70<sup>o</sup>C the tetrahedral intermediate is stable. It collapses to the aldehyde on aqueous work-up (slow quenching with methanol followed by full quenching with water), but by this stage excess DIBAL has been destroyed so as to prevent any further reduction.

==Reduction of Nitriles to Aldehydes using DIBAL==

[[Image:Nitrile3.png]]

<ref>http://www.cliffsnotes.com/WileyCDA/CliffsReviewTopic/Synthesis-of-Aldehydes.topicArticleId-23297,articleId-23278.html</ref>

Mechanism:

i. The first step of this mechanism involves an acid-base reaction between a lone pair of electrons on N with the AL in DIBAL.

ii. The second step involves the transfer of a hydride ion from DIBAL to the C of the nitrile group.

iii. The final step is the hydrolysis of the aluminium complex which results in the formation of the desired aldehyde.

==Safety Information==
Neat DIBAL is pyrophoric (capable of igniting spontaneously in air), and its solutions react violently with water, oxygen and other related compounds. It should always be handled with care in a fume hood.

<ref>http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/256811</ref>

===Potential Health Effects===

*Eye: Causes eye burns.
*Skin: Causes skin burns.
*Ingestion: Causes gastrointestinal tract burns.
*Inhalation: Harmful if inhaled. Causes chemical burns to the respiratory tract.

NOTE: Only use dry chemical to extinguish DIBAL-induced fires. DO NOT USE WATER.

==References==
<references/>

It07:DIBAL

2007-12-05T11:29:14Z

Zh206: /* DIBAL Di-IsoButyl Aluminium Hydride */

=DIBAL Di-IsoButyl Aluminium Hydride=
[[Image:DIBAL1.png]]

<jmol>
<jmolApplet>
<title>DIBAL</title><color>yellow</color>
<size>200</size>
<script>zoom 80; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>DIBAL10.mol</uploadedFileContents>
</jmolApplet>

<jmolMenu>
<item><text>Start spinning</text><script>spin on</script></item>
<item><text>Stop spinning</text><script>spin off</script></item>
<menuHeight>-1</menuHeight>
</jmolMenu>
<jmolButton>
<script>console</script>
<text>open a console window</text>
</jmolButton>
</jmol>

<jmol>
<jmolAppletButton>
<title>Show DIBAL in popup window</title>
<color>cyan</color>
<uploadedFileContents>DIBAL10.mol</uploadedFileContents>
</jmolAppletButton>
</jmol>

<noinclude>

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | {{PAGENAME}} 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:DIBAL1.png|200px|{{PAGENAME}}]] 
|-
! {{chembox header}} | General
|-
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]
| Di-Isobutyl Aluminium Hydride

|-
| Other names
| DIBAL, DIBAL-H, DIBAH, DIBALH
|-
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| [(CH3)2CHCH2]2AlH
|-
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] 
| [H][Al]CC(C)C.CCC(C)C
|-
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| 142.22
|-
| Appearance
| Clear, colourless liquid
|-
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| 1191-15-7
|-
! {{chembox header}} | Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] & [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]
| 0.798 g/cm³ 
|-



| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| 255.15 K 
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| 389.15-391.15 K
|-
! {{chembox header}} | Hazards 
|-
| [[Material safety data sheet|MSDS]]
| [[{{PAGENAME}} (data page)#Material Safety Data Sheet|External MSDS]] 
|-
| Main [[Worker safety and health|hazard]]s
| Corrosive, highly flammable. 
|-
|-
|-
|-
|-

|-
|-
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic<br />data]]
| Liquid
|-
|-
! {{chembox header}} | 3-D Structure
|-
|-
|3D
|<jmol>
<jmolApplet>
<title>DIBAL</title><color>yellow</color>
<size>250</size>
<script>zoom 120; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>DIBAL.mol</uploadedFileContents>
</jmolApplet>
<jmolMenu>
<item><text>Start spinning</text><script>spin on</script></item>
<item><text>Stop spinning</text><script>spin off</script></item>
<menuHeight>-1</menuHeight>
</jmolMenu>
</jmol>
|-
|-
|-
|-
|-
|-
|}

==Introduction==

<ref>http://www.akzonobel-polymerchemicals.com/NR/rdonlyres/CB29DA1C-1144-47F4-888A-B20FC61E17F5/11037/Diisobutylaluminumhydride_ma_row_eng_tb.pdf</ref>
DIBAL has rapidly established itself as a reducing agent of choice in organic synthesis. It is most effective at reducing electron-rich carbonyl groups and has largely replaced the use of metal hydrides (including LiAlH<sub>4</sub> and NaBH<sub>4</sub>) due to economic advantages. It demonstrates increased selectivity and a considerably lower cost per reducing equivalent. It is also a particularly easy-handling material as it is a liquid that is miscible in many solvents.
DIBAL exists as a dimer due to increased stabilisation:
[[Image:DIBAL6.png]]

==Reduction of Esters to Aldehydes using DIBAL==

Chemists often come across a problem when reducing an ester to an aldehyde. This is because the aldehyde product is more susceptible to reduction than the starting ester and therefore the reduction process continues to the next oxidation level – to the alcohol.
DIBAL, however, can be used as a reagent that will carry out this reduction in 1 step and stops at the aldehyde without further reduction.

[[Image:Ester3.png]]

<ref>“ORGANIC CHEMISTRY” Clayden, Greeves, Warren & Wothers</ref>

At -70<sup>o</sup>C the tetrahedral intermediate is stable. It collapses to the aldehyde on aqueous work-up (slow quenching with methanol followed by full quenching with water), but by this stage excess DIBAL has been destroyed so as to prevent any further reduction.

==Reduction of Nitriles to Aldehydes using DIBAL==

[[Image:Nitrile3.png]]

<ref>http://www.cliffsnotes.com/WileyCDA/CliffsReviewTopic/Synthesis-of-Aldehydes.topicArticleId-23297,articleId-23278.html</ref>

Mechanism:

i. The first step of this mechanism involves an acid-base reaction between a lone pair of electrons on N with the AL in DIBAL.

ii. The second step involves the transfer of a hydride ion from DIBAL to the C of the nitrile group.

iii. The final step is the hydrolysis of the aluminium complex which results in the formation of the desired aldehyde.

==Safety Information==
Neat DIBAL is pyrophoric (capable of igniting spontaneously in air), and its solutions react violently with water, oxygen and other related compounds. It should always be handled with care in a fume hood.

<ref>http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/256811</ref>

===Potential Health Effects===

*Eye: Causes eye burns.
*Skin: Causes skin burns.
*Ingestion: Causes gastrointestinal tract burns.
*Inhalation: Harmful if inhaled. Causes chemical burns to the respiratory tract.

NOTE: Only use dry chemical to extinguish DIBAL-induced fires. DO NOT USE WATER.

==References==
<references/>

It07:DIBAL

2007-12-05T11:23:56Z

Zh206: /* DIBAL Di-IsoButyl Aluminium Hydride */

=DIBAL Di-IsoButyl Aluminium Hydride=
[[Image:DIBAL1.png]]

<jmol>
<jmolApplet>
<title>DIBAL</title><color>yellow</color>
<size>200</size>
<script>zoom 80; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>DIBAL10.mol</uploadedFileContents>
</jmolApplet>

<jmolMenu>
<item><text>Start spinning</text><script>spin on</script></item>
<item><text>Stop spinning</text><script>spin off</script></item>
<menuHeight>-1</menuHeight>
</jmolMenu>
<jmolButton>
<script>console</script>
<text>open a console window</text>
</jmolButton>
</jmol>

<jmol>
<jmolAppletButton>
<title>Show Pentahelicene in popup window</title>
<color>cyan</color>
<uploadedFileContents>DIBAL10.mol</uploadedFileContents>
</jmolAppletButton>
</jmol>

<noinclude>

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | {{PAGENAME}} 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:DIBAL1.png|200px|{{PAGENAME}}]] 
|-
! {{chembox header}} | General
|-
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]
| Di-Isobutyl Aluminium Hydride

|-
| Other names
| DIBAL, DIBAL-H, DIBAH, DIBALH
|-
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| [(CH3)2CHCH2]2AlH
|-
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] 
| [H][Al]CC(C)C.CCC(C)C
|-
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| 142.22
|-
| Appearance
| Clear, colourless liquid
|-
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| 1191-15-7
|-
! {{chembox header}} | Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] & [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]
| 0.798 g/cm³ 
|-



| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| 255.15 K 
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| 389.15-391.15 K
|-
! {{chembox header}} | Hazards 
|-
| [[Material safety data sheet|MSDS]]
| [[{{PAGENAME}} (data page)#Material Safety Data Sheet|External MSDS]] 
|-
| Main [[Worker safety and health|hazard]]s
| Corrosive, highly flammable. 
|-
|-
|-
|-
|-

|-
|-
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic<br />data]]
| Liquid
|-
|-
! {{chembox header}} | 3-D Structure
|-
|-
|3D
|<jmol>
<jmolApplet>
<title>DIBAL</title><color>yellow</color>
<size>250</size>
<script>zoom 120; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>DIBAL.mol</uploadedFileContents>
</jmolApplet>
<jmolMenu>
<item><text>Start spinning</text><script>spin on</script></item>
<item><text>Stop spinning</text><script>spin off</script></item>
<menuHeight>-1</menuHeight>
</jmolMenu>
</jmol>
|-
|-
|-
|-
|-
|-
|}

==Introduction==

<ref>http://www.akzonobel-polymerchemicals.com/NR/rdonlyres/CB29DA1C-1144-47F4-888A-B20FC61E17F5/11037/Diisobutylaluminumhydride_ma_row_eng_tb.pdf</ref>
DIBAL has rapidly established itself as a reducing agent of choice in organic synthesis. It is most effective at reducing electron-rich carbonyl groups and has largely replaced the use of metal hydrides (including LiAlH<sub>4</sub> and NaBH<sub>4</sub>) due to economic advantages. It demonstrates increased selectivity and a considerably lower cost per reducing equivalent. It is also a particularly easy-handling material as it is a liquid that is miscible in many solvents.
DIBAL exists as a dimer due to increased stabilisation:
[[Image:DIBAL6.png]]

==Reduction of Esters to Aldehydes using DIBAL==

Chemists often come across a problem when reducing an ester to an aldehyde. This is because the aldehyde product is more susceptible to reduction than the starting ester and therefore the reduction process continues to the next oxidation level – to the alcohol.
DIBAL, however, can be used as a reagent that will carry out this reduction in 1 step and stops at the aldehyde without further reduction.

[[Image:Ester3.png]]

<ref>“ORGANIC CHEMISTRY” Clayden, Greeves, Warren & Wothers</ref>

At -70<sup>o</sup>C the tetrahedral intermediate is stable. It collapses to the aldehyde on aqueous work-up (slow quenching with methanol followed by full quenching with water), but by this stage excess DIBAL has been destroyed so as to prevent any further reduction.

==Reduction of Nitriles to Aldehydes using DIBAL==

[[Image:Nitrile3.png]]

<ref>http://www.cliffsnotes.com/WileyCDA/CliffsReviewTopic/Synthesis-of-Aldehydes.topicArticleId-23297,articleId-23278.html</ref>

Mechanism:

i. The first step of this mechanism involves an acid-base reaction between a lone pair of electrons on N with the AL in DIBAL.

ii. The second step involves the transfer of a hydride ion from DIBAL to the C of the nitrile group.

iii. The final step is the hydrolysis of the aluminium complex which results in the formation of the desired aldehyde.

==Safety Information==
Neat DIBAL is pyrophoric (capable of igniting spontaneously in air), and its solutions react violently with water, oxygen and other related compounds. It should always be handled with care in a fume hood.

<ref>http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/256811</ref>

===Potential Health Effects===

*Eye: Causes eye burns.
*Skin: Causes skin burns.
*Ingestion: Causes gastrointestinal tract burns.
*Inhalation: Harmful if inhaled. Causes chemical burns to the respiratory tract.

NOTE: Only use dry chemical to extinguish DIBAL-induced fires. DO NOT USE WATER.

==References==
<references/>

File:DIBAL10.mol

2007-12-05T11:21:57Z

Zh206:

It07:DIBAL

2007-12-05T11:12:34Z

Zh206: /* DIBAL Di-IsoButyl Aluminium Hydride */

=DIBAL Di-IsoButyl Aluminium Hydride=
[[Image:DIBAL1.png]]

|3D
|<jmol>
<jmolApplet>
<title>DIBAL</title><color>yellow</color>
<size>250</size>
<script>zoom 120; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>DIBAL10.mol</uploadedFileContents>
</jmolApplet>
<jmolMenu>
<item><text>Start spinning</text><script>spin on</script></item>
<item><text>Stop spinning</text><script>spin off</script></item>
<menuHeight>-1</menuHeight>
</jmolMenu>
</jmol>

<noinclude>

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | {{PAGENAME}} 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:DIBAL1.png|200px|{{PAGENAME}}]] 
|-
! {{chembox header}} | General
|-
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]
| Di-Isobutyl Aluminium Hydride

|-
| Other names
| DIBAL, DIBAL-H, DIBAH, DIBALH
|-
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| [(CH3)2CHCH2]2AlH
|-
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] 
| [H][Al]CC(C)C.CCC(C)C
|-
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| 142.22
|-
| Appearance
| Clear, colourless liquid
|-
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| 1191-15-7
|-
! {{chembox header}} | Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] & [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]
| 0.798 g/cm³ 
|-



| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| 255.15 K 
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| 389.15-391.15 K
|-
! {{chembox header}} | Hazards 
|-
| [[Material safety data sheet|MSDS]]
| [[{{PAGENAME}} (data page)#Material Safety Data Sheet|External MSDS]] 
|-
| Main [[Worker safety and health|hazard]]s
| Corrosive, highly flammable. 
|-
|-
|-
|-
|-

|-
|-
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic<br />data]]
| Liquid
|-
|-
! {{chembox header}} | 3-D Structure
|-
|-
|3D
|<jmol>
<jmolApplet>
<title>DIBAL</title><color>yellow</color>
<size>250</size>
<script>zoom 120; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>DIBAL.mol</uploadedFileContents>
</jmolApplet>
<jmolMenu>
<item><text>Start spinning</text><script>spin on</script></item>
<item><text>Stop spinning</text><script>spin off</script></item>
<menuHeight>-1</menuHeight>
</jmolMenu>
</jmol>
|-
|-
|-
|-
|-
|-
|}

==Introduction==

<ref>http://www.akzonobel-polymerchemicals.com/NR/rdonlyres/CB29DA1C-1144-47F4-888A-B20FC61E17F5/11037/Diisobutylaluminumhydride_ma_row_eng_tb.pdf</ref>
DIBAL has rapidly established itself as a reducing agent of choice in organic synthesis. It is most effective at reducing electron-rich carbonyl groups and has largely replaced the use of metal hydrides (including LiAlH<sub>4</sub> and NaBH<sub>4</sub>) due to economic advantages. It demonstrates increased selectivity and a considerably lower cost per reducing equivalent. It is also a particularly easy-handling material as it is a liquid that is miscible in many solvents.
DIBAL exists as a dimer due to increased stabilisation:
[[Image:DIBAL6.png]]

==Reduction of Esters to Aldehydes using DIBAL==

Chemists often come across a problem when reducing an ester to an aldehyde. This is because the aldehyde product is more susceptible to reduction than the starting ester and therefore the reduction process continues to the next oxidation level – to the alcohol.
DIBAL, however, can be used as a reagent that will carry out this reduction in 1 step and stops at the aldehyde without further reduction.

[[Image:Ester3.png]]

<ref>“ORGANIC CHEMISTRY” Clayden, Greeves, Warren & Wothers</ref>

At -70<sup>o</sup>C the tetrahedral intermediate is stable. It collapses to the aldehyde on aqueous work-up (slow quenching with methanol followed by full quenching with water), but by this stage excess DIBAL has been destroyed so as to prevent any further reduction.

==Reduction of Nitriles to Aldehydes using DIBAL==

[[Image:Nitrile3.png]]

<ref>http://www.cliffsnotes.com/WileyCDA/CliffsReviewTopic/Synthesis-of-Aldehydes.topicArticleId-23297,articleId-23278.html</ref>

Mechanism:

i. The first step of this mechanism involves an acid-base reaction between a lone pair of electrons on N with the AL in DIBAL.

ii. The second step involves the transfer of a hydride ion from DIBAL to the C of the nitrile group.

iii. The final step is the hydrolysis of the aluminium complex which results in the formation of the desired aldehyde.

==Safety Information==
Neat DIBAL is pyrophoric (capable of igniting spontaneously in air), and its solutions react violently with water, oxygen and other related compounds. It should always be handled with care in a fume hood.

<ref>http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/256811</ref>

===Potential Health Effects===

*Eye: Causes eye burns.
*Skin: Causes skin burns.
*Ingestion: Causes gastrointestinal tract burns.
*Inhalation: Harmful if inhaled. Causes chemical burns to the respiratory tract.

NOTE: Only use dry chemical to extinguish DIBAL-induced fires. DO NOT USE WATER.

==References==
<references/>

It07:DIBAL

=DIBAL Di-IsoButyl Aluminium Hydride=
[[Image:DIBAL1.png]]

<noinclude>

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | {{PAGENAME}} 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:{{PAGENAME}}.jpg|200px|{{PAGENAME}}]] 
|-
! {{chembox header}} | General
|-
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]
| Di-Isobutyl Aluminium Hydride

|-
| Other names
| DIBAL, DIBAL-H, DIBAH
|-
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| [(CH3)2CHCH2]2AlH
|-
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] 
| [H][Al]CC(C)C.CCC(C)C
|-
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| 142.22
|-
| Appearance
| Clear, colourless liquid
|-
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| 1191-15-7
|-
! {{chembox header}} | Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] & [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]
| 0.798 g/cm³ 
|-



| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| 255.15 K 
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| 389.15-391.15 K
|-
! {{chembox header}} | Hazards 
|-
| [[Material safety data sheet|MSDS]]
| [[{{PAGENAME}} (data page)#Material Safety Data Sheet|External MSDS]] 
|-
| Main [[Worker safety and health|hazard]]s
| Corrosive, highly flammable. 
|-
| [[NFPA 704]]
| {{{NFPA}}}
|-
| [[Flash point]]
| {{{Fp}}}°C
|-
| [[Risk and Safety Statements|R/S statement]]
| [[List of R-phrases|R]]: {{{R-S}}} <br /> [[List of S-phrases|S]]: ?
|-
| [[RTECS]] number
| {{{RTECS}}}
|-
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and<br />properties]]
| [http://en.wikipedia.org/wiki/Refractive_index ''n''], [http://en.wikipedia.org/wiki/Dielectric_constant ε<sub>r</sub>], etc.
|-
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic<br />data]]
| Phase behaviour<br />Solid, liquid, gas
|-
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} | Related compounds
|-
| Other [[Ion|anion]]s 
| {{{Other_anion}}} 
|-
| Other [[Ion|cation]]s 
| {{{Ohter_cation}}} 
|-
| Related compounds

| {{{Relative_Compounds}}}
|-
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25 °C, 100 kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small>
|-
|}
{{Chem-Data_Structure}}

==Introduction==
DIBAL has rapidly established itself as a reducing agent of choice in organic synthesis. It is most effective at reducing electron-rich carbonyl groups and has largely replaced the use of metal hydrides (including LiAlH4 and NaBH4) due to economic advantages. It demonstrates increased selectivity and a considerably lower cost per reducing equivalent. It is also a particularly easy-handling material as it is a liquid that is miscible in many solvents.
DIBAL exists as a dimer due to increased stabilisation:
[[Image:DIBAL6.png]]

==Reduction of Esters to Aldehydes using DIBAL==

Chemists often come across a problem when reducing an ester to an aldehyde. This is because the aldehyde product is more susceptible to reduction than the starting ester and therefore the reduction process continues to the next oxidation level – to the alcohol.
DIBAL, however, can be used as a reagent that will carry out this reduction in 1 step and stops at the aldehyde without further reduction.

[[Image:Ester3.png]]

At -70<sup>o</sup>C the tetrahedral intermediate is stable. It collapses to the aldehyde on aqueous work-up (slow quenching with methanol followed by full quenching with water), but by this stage excess DIBAL has been destroyed so as to prevent any further reduction.

==Reduction of Nitriles to Aldehydes using DIBAL==

[[Image:Nitrile3.png]]

Mechanism:

i. The first step of this mechanism involves an acid-base reaction between a lone pair of electrons on N with the AL in DIBAL.

ii. The second step involves the transfer of a hydride ion from DIBAL to the C of the nitrile group.

iii. The final step is the hydrolysis of the aluminium complex which results in the formation of the desired aldehyde.

==Safety Information==
Neat DIBAL is pyrophoric (capable of igniting spontaneously in air), and its solutions react violently with water, oxygen and other related compounds. It should always be handled with care in a fume hood.

It07:DIBAL

2007-11-30T11:29:28Z

Zh206: /* DIBAL Di-IsoButyl Aluminium Hydride */

=DIBAL Di-IsoButyl Aluminium Hydride=
[[Image:DIBAL1.png]]

<noinclude>

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | {{PAGENAME}} 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:{{PAGENAME}}.jpg|200px|{{PAGENAME}}]] 
|-
! {{chembox header}} | General
|-
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]
| Di-Isobutyl Aluminium Hydride

|-
| Other names
| DIBAL, DIBAL-H, DIBAH
|-
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| [(CH3)2CHCH2]2AlH
|-
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] 
| [H][Al]CC(C)C.CCC(C)C
|-
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| 142.22
|-
| Appearance
| Clear, colourless liquid
|-
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| 1191-15-7
|-
! {{chembox header}} | Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] & [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]
| 0.798 g/cm³ 
|-



| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| 255.15 K 
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| 389.15-391.15 K
|-
! {{chembox header}} | Hazards 
|-
| [[Material safety data sheet|MSDS]]
| [[{{PAGENAME}} (data page)#Material Safety Data Sheet|External MSDS]] 
|-
| Main [[Worker safety and health|hazard]]s
| Corrosive, highly flammable. 
|-
| [[NFPA 704]]
| {{{NFPA}}}
|-
| [[Flash point]]
| {{{Fp}}}°C
|-
| [[Risk and Safety Statements|R/S statement]]
| [[List of R-phrases|R]]: {{{R-S}}} <br /> [[List of S-phrases|S]]: ?
|-
| [[RTECS]] number
| {{{RTECS}}}
|-
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and<br />properties]]
| [http://en.wikipedia.org/wiki/Refractive_index ''n''], [http://en.wikipedia.org/wiki/Dielectric_constant ε<sub>r</sub>], etc.
|-
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic<br />data]]
| Phase behaviour<br />Solid, liquid, gas
|-
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} | Related compounds
|-
| Other [[Ion|anion]]s 
| {{{Other_anion}}} 
|-
| Other [[Ion|cation]]s 
| {{{Ohter_cation}}} 
|-
| Related compounds

| {{{Relative_Compounds}}}
|-
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25 °C, 100 kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small>
|-
|}
{{Chem-Data_Structure}}

==Introduction==
DIBAL has rapidly established itself as a reducing agent of choice in organic synthesis. It is most effective at reducing electron-rich carbonyl groups and has largely replaced the use of metal hydrides (including LiAlH4 and NaBH4) due to economic advantages. It demonstrates increased selectivity and a considerably lower cost per reducing equivalent. It is also a particularly easy-handling material as it is a liquid that is miscible in many solvents.
DIBAL exists as a dimer due to increased stabilisation:
[[Image:DIBAL6.png]]

==Reduction of Esters to Aldehydes using DIBAL==

Chemists often come across a problem when reducing an ester to an aldehyde. This is because the aldehyde product is more susceptible to reduction than the starting ester and therefore the reduction process continues to the next oxidation level – to the alcohol.
DIBAL, however, can be used as a reagent that will carry out this reduction in 1 step and stops at the aldehyde without further reduction.

[[Image:Ester3.png]]

At -70<sup>o</sup>C the tetrahedral intermediate is stable. It collapses to the aldehyde on aqueous work-up (slow quenching with methanol followed by full quenching with water), but by this stage excess DIBAL has been destroyed so as to prevent any further reduction.

==Reduction of Nitriles to Aldehydes using DIBAL==

[[Image:Nitrile3.png]]

Mechanism:

i. The first step of this mechanism involves an acid-base reaction between a lone pair of electrons on N with the AL in DIBAL.

ii. The second step involves the transfer of a hydride ion from DIBAL to the C of the nitrile group.

iii. The final step is the hydrolysis of the aluminium complex which results in the formation of the desired aldehyde.

It07:DIBAL

2007-11-30T11:17:15Z

Zh206: /* DIBAL Di-IsoButyl Aluminium Hydride */

=DIBAL Di-IsoButyl Aluminium Hydride=
[[Image:DIBAL1.png]]

<noinclude>

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | {{PAGENAME}} 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:{{PAGENAME}}.jpg|200px|{{PAGENAME}}]] 
|-
! {{chembox header}} | General
|-
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]
| Di-Isobutyl Aluminium Hydride

|-
| Other names
| DIBAL, DIBAL-H, DIBAH
|-
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| [(CH3)2CHCH2]2AlH
|-
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] 
| [H][Al]CC(C)C.CCC(C)C
|-
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| 142.22
|-
| Appearance
| Clear, colourless liquid
|-
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| 1191-15-7
|-
! {{chembox header}} | Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] & [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]
| 0.798 g/cm³ 
|-



| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| 255.15 K 
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| 389.15-391.15 K
|-
! {{chembox header}} | Hazards 
|-
| [[Material safety data sheet|MSDS]]
| [[{{PAGENAME}} (data page)#Material Safety Data Sheet|External MSDS]] 
|-
| Main [[Worker safety and health|hazard]]s
| Corrosive, highly flammable. Neat DIBAL is pyrophoric and reacts violently with water, oxygen and other related compounds. 
|-
| [[NFPA 704]]
| {{{NFPA}}}
|-
| [[Flash point]]
| {{{Fp}}}°C
|-
| [[Risk and Safety Statements|R/S statement]]
| [[List of R-phrases|R]]: {{{R-S}}} <br /> [[List of S-phrases|S]]: ?
|-
| [[RTECS]] number
| {{{RTECS}}}
|-
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and<br />properties]]
| [http://en.wikipedia.org/wiki/Refractive_index ''n''], [http://en.wikipedia.org/wiki/Dielectric_constant ε<sub>r</sub>], etc.
|-
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic<br />data]]
| Phase behaviour<br />Solid, liquid, gas
|-
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} | Related compounds
|-
| Other [[Ion|anion]]s 
| {{{Other_anion}}} 
|-
| Other [[Ion|cation]]s 
| {{{Ohter_cation}}} 
|-
| Related compounds

| {{{Relative_Compounds}}}
|-
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25 °C, 100 kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small>
|-
|}
{{Chem-Data_Structure}}

==Introduction==
DIBAL has rapidly established itself as a reducing agent of choice in organic synthesis. It is most effective at reducing electron-rich carbonyl groups and has largely replaced the use of metal hydrides (including LiAlH4 and NaBH4) due to economic advantages. It demonstrates increased selectivity and a considerably lower cost per reducing equivalent. It is also a particularly easy-handling material as it is a liquid that is miscible in many solvents.
DIBAL exists as a dimer due to increased stabilisation:
[[Image:DIBAL6.png]]

==Reduction of Esters to Aldehydes using DIBAL==

Chemists often come across a problem when reducing an ester to an aldehyde. This is because the aldehyde product is more susceptible to reduction than the starting ester and therefore the reduction process continues to the next oxidation level – to the alcohol.
DIBAL, however, can be used as a reagent that will carry out this reduction in 1 step and stops at the aldehyde without further reduction.

[[Image:Ester3.png]]

At -70<sup>o</sup>C the tetrahedral intermediate is stable. It collapses to the aldehyde on aqueous work-up (slow quenching with methanol followed by full quenching with water), but by this stage excess DIBAL has been destroyed so as to prevent any further reduction.

==Reduction of Nitriles to Aldehydes using DIBAL==

[[Image:Nitrile3.png]]

Mechanism:

i. The first step of this mechanism involves an acid-base reaction between a lone pair of electrons on N with the AL in DIBAL.

ii. The second step involves the transfer of a hydride ion from DIBAL to the C of the nitrile group.

iii. The final step is the hydrolysis of the aluminium complex which results in the formation of the desired aldehyde.

It07:DIBAL

2007-11-29T18:46:41Z

Zh206: /* DIBAL Di-IsoButyl Aluminium Hydride */

=DIBAL Di-IsoButyl Aluminium Hydride=
[[Image:DIBAL1.png]]

<noinclude>

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | {{PAGENAME}} 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:{{PAGENAME}}.jpg|200px|{{PAGENAME}}]] 
|-
! {{chembox header}} | General
|-
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]
| Di-Isobutyl Aluminium Hydride

|-
| Other names
| DIBAL, DIBAL-H, DIBAH
|-
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| [(CH3)2CHCH2]2AlH
|-
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] 
| [H][Al]CC(C)C.CCC(C)C
|-
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| 142.22
|-
| Appearance
| Clear, colourless liquid
|-
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| 1191-15-7
|-
! {{chembox header}} | Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] & [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]
| 0.798 g/cm³ 
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility in water]
| {{{Sol_Water}}} g/100 ml (25°C) 
|-



| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| {{{Mp}}} K 
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| {{{Bp}}} K
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Acidity] (p''K''<sub>a</sub>) 
| {{{pKa}}}
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K''<sub>b</sub>) 
| {{{pKb}}}
|-
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation <nowiki>[α]</nowiki><sub>D</sub>] 
| {{{Rotation}}}°
|-
| [http://en.wikipedia.org/wiki/Viscosity Viscosity]
| {{{Viscosity}}} [[Poise|cP]] at 25°C 
|-
! {{chembox header}} | Structure
|-
| [http://en.wikipedia.org/wiki/Orbital_hybridisation Molecular shape] 
| {{{Mol_Shape}}} 
|-
| [http://en.wikipedia.org/wiki/Coordination_geometry Coordination<br />geometry] 
| {{{Coordination}}} 
|-
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] 
| {{{Crystal_Structure}}} 
|-
| [[Dipole#Molecular_dipoles|Dipole moment]]
| {{{DM}}} [[Debye|D]]
|-
! {{chembox header}} | Hazards 
|-
| [[Material safety data sheet|MSDS]]
| [[{{PAGENAME}} (data page)#Material Safety Data Sheet|External MSDS]] 
|-
| Main [[Worker safety and health|hazard]]s
| {{{Hazards}}} 
|-
| [[NFPA 704]]
| {{{NFPA}}}
|-
| [[Flash point]]
| {{{Fp}}}°C
|-
| [[Risk and Safety Statements|R/S statement]]
| [[List of R-phrases|R]]: {{{R-S}}} <br /> [[List of S-phrases|S]]: ?
|-
| [[RTECS]] number
| {{{RTECS}}}
|-
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and<br />properties]]
| [http://en.wikipedia.org/wiki/Refractive_index ''n''], [http://en.wikipedia.org/wiki/Dielectric_constant ε<sub>r</sub>], etc.
|-
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic<br />data]]
| Phase behaviour<br />Solid, liquid, gas
|-
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} | Related compounds
|-
| Other [[Ion|anion]]s 
| {{{Other_anion}}} 
|-
| Other [[Ion|cation]]s 
| {{{Ohter_cation}}} 
|-
| Related compounds

| {{{Relative_Compounds}}}
|-
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25 °C, 100 kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small>
|-
|}
{{Chem-Data_Structure}}

==Introduction==
DIBAL has rapidly established itself as a reducing agent of choice in organic synthesis. It is most effective at reducing electron-rich carbonyl groups and has largely replaced the use of metal hydrides (including LiAlH4 and NaBH4) due to economic advantages. It demonstrates increased selectivity and a considerably lower cost per reducing equivalent. It is also a particularly easy-handling material as it is a liquid that is miscible in many solvents.
DIBAL exists as a dimer due to increased stabilisation:
[[Image:DIBAL6.png]]

==Reduction of Esters to Aldehydes using DIBAL==

Chemists often come across a problem when reducing an ester to an aldehyde. This is because the aldehyde product is more susceptible to reduction than the starting ester and therefore the reduction process continues to the next oxidation level – to the alcohol.
DIBAL, however, can be used as a reagent that will carry out this reduction in 1 step and stops at the aldehyde without further reduction.

[[Image:Ester3.png]]

At -70<sup>o</sup>C the tetrahedral intermediate is stable. It collapses to the aldehyde on aqueous work-up (slow quenching with methanol followed by full quenching with water), but by this stage excess DIBAL has been destroyed so as to prevent any further reduction.

==Reduction of Nitriles to Aldehydes using DIBAL==

[[Image:Nitrile3.png]]

Mechanism:

i. The first step of this mechanism involves an acid-base reaction between a lone pair of electrons on N with the AL in DIBAL.

ii. The second step involves the transfer of a hydride ion from DIBAL to the C of the nitrile group.

iii. The final step is the hydrolysis of the aluminium complex which results in the formation of the desired aldehyde.

It07:DIBAL

2007-11-29T18:37:50Z

File:DIBAL4.png

2007-11-29T18:26:02Z

Zh206: