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Diisobutylaluminium hydride

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Name

Diisobutylaluminium hydride

EINECS 214-729-9
CAS No. 1191-15-7 Density 0.848 g/cm3
PSA 0.00000 LogP 3.33250
Solubility vigorous reaction with water, soluble in most organic solvents Melting Point -70 °C
Formula C8H19Al Boiling Point 110 °C
Molecular Weight 142.22 Flash Point 4 °C
Transport Information UN 3399 4.3/PG 1 Appearance Clear solution
Safety 26-43-45-62-46-36/37/39-29-16-61-27 Risk Codes 14/15-17-35-40-67-65-63-48/20-11-19-62-51/53-23/24/25-20/21/22
Molecular Structure Molecular Structure of 1191-15-7 (Diisobutylaluminium hydride) Hazard Symbols ToxicT,FlammableF,CorrosiveC,DangerousN
Synonyms

Aluminum,hydrodiisobutyl- (8CI);Diisobutylaluminum hydride (6CI);Bis(iso-butyl)aluminum hydride;Bis(isobutyl)aluminum hydride;Bis(isobutyl)hydroaluminum;DIBAH;DIBAL-H;Di-iso-butylaluminum hydride;Dibal;Diisobutylalane;Diisobutylaluminium hydride;Diisobutylhydroaluminum;Hydrodiisobutylaluminum;

Article Data 11

Diisobutylaluminium hydride Synthetic route

100-99-2

triisobutylaluminum

1191-15-7

diisobutylaluminium hydride

60-29-7

diethyl ether

1191-15-7

diisobutylaluminium hydride

Conditions
ConditionsYield
With hydrogenchloride; diisobutylaluminium hydride In tetrahydrofuran; methanol
With hydrogenchloride; diisobutylaluminium hydride In tetrahydrofuran; methanol
With hydrogenchloride; diisobutylaluminium hydride In tetrahydrofuran; methanol
100-99-2

triisobutylaluminum

A

5587-58-6

diisobutyl aluminium (1+); isobutylate

B

1191-15-7

diisobutylaluminium hydride

Conditions
ConditionsYield
With water bubbling moistened helium stream (O2<0.001%) through Al-compd. (Drechsel vessel, room temp.); gas-liquid chromatographic anal., mass spectroscopy;

[rac-1,2-ethylene-bis(η5-4,5,6,7-tetrahydroindenyl)]dichloridezirconium(IV)

1779-25-5

diisobutylaluminum chloride

rac-C2H4(4,5,6,7-tetrahydroindenyl)2ZrCl(μ-H)2Al(i-Bu)2

rac-C2H4(4,5,6,7-tetrahydroindenyl)2ZrCl(μ-H)2Al(i-Bu)2

rac-C2H4(4,5,6,7-tetrahydroindenyl)2ZrH(μ-H)2Al(i-Bu)2

C

1191-15-7

diisobutylaluminium hydride

Conditions
ConditionsYield
In (2)H8-toluene toluene-d7, 1 equiv of Al-compound, 25°C; not sepd., detected by NMR spectra;
873-31-4

2-chlorophenylacetylene

1191-15-7

diisobutylaluminium hydride

A

ClC6H4CHCHAl(CH2CH(CH3)2)2

B

ClC6H4CCAl(CH2CH(CH3)2)2

C

Conditions
ConditionsYield
1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In tetrahydrofuran 3 mol% of Ni-catalyst, 1.3 equiv of Al-compound, THF, 22°C, 2 h, N2 atm.; detected by NMR spectra after quench with D2O (0°C, 30 min); α:β= >98:2;A n/a
B 2%
C n/a
1-ethynyl-3-methoxybenzene

1-ethynyl-3-methoxybenzene

1191-15-7

diisobutylaluminium hydride

A

CH3OC6H4CHCHAl(CH2CH(CH3)2)2

B

CH3OC6H4CCAl(CH2CH(CH3)2)2

C

CH3OC6H4CCH2Al(CH2CH(CH3)2)2

Conditions
ConditionsYield
1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In tetrahydrofuran 3 mol% of Ni-catalyst, 1.3 equiv of Al-compound, THF, 22°C, 2 h, N2 atm.; detected by NMR spectra after quench with D2O (0°C, 30 min); α:β=>98:2;A n/a
B 2%
C n/a
67237-53-0

3-ethynylthiophene

1191-15-7

diisobutylaluminium hydride

A

C4H3SCHCHAl(CH2CH(CH3)2)2

B

C4H3SCCAl(CH2CH(CH3)2)2

C

C4H3SCCH2Al(CH2CH(CH3)2)2

Conditions
ConditionsYield
1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In tetrahydrofuran 3 mol% of Ni-catalyst, 1.3 equiv of Al-compound, THF, 22°C, 2 h, N2 atm.; detected by NMR spectra after quench with D2O (0°C, 30 min); α:β= >98:2;A n/a
B 2%
C n/a
705-28-2

1-ethynyl-3-trifluoromethylbenzene

1191-15-7

diisobutylaluminium hydride

A

CF3C6H4CHCHAl(CH2CH(CH3)2)2

B

CF3C6H4CCH2Al(CH2CH(CH3)2)2

C

CF3C6H4CCAl(CH2CH(CH3)2)2

Conditions
ConditionsYield
1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In tetrahydrofuran 3 mol% of Ni-catalyst, 1.3 equiv of Al-compound, THF, 4°C, 12 h, N2 atm.; detected by NMR spectra after quench with D2O (0°C, 30 min); α:β= 95:5;A n/a
B n/a
C 2%
2510-23-8

3-Ethynylpyridine

1191-15-7

diisobutylaluminium hydride

A

C5H4NCHCHAl(CH2CH(CH3)2)2

B

C5H4NCCAl(CH2CH(CH3)2)2

C

C5H4NCCH2Al(CH2CH(CH3)2)2

Conditions
ConditionsYield
1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In tetrahydrofuran 3 mol% of Ni-catalyst, 1.3 equiv of Al-compound, THF, 22°C, 2 h, N2 atm.; detected by NMR spectra after quench with D2O (0°C, 30 min); α:β= >98:2;A n/a
B 2%
C n/a
767-91-9

1-ethynyl-2-methoxybenzene

1191-15-7

diisobutylaluminium hydride

A

CH3OC6H4CHCHAl(CH2CH(CH3)2)2

B

CH3OC6H4CCAl(CH2CH(CH3)2)2

C

CH3OC6H4CCH2Al(CH2CH(CH3)2)2

Conditions
ConditionsYield
1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In tetrahydrofuran 3 mol% of Ni-catalyst, 1.3 equiv of Al-compound, THF, 4°C, 12 h, N2 atm.; detected by NMR spectra after quench with D2O (0°C, 30 min); α:β=98:2;A n/a
B 2%
C n/a

Diisobutylaluminium hydride Consensus Reports

Reported in EPA TSCA Inventory.

Diisobutylaluminium hydride Standards and Recommendations

ACGIH TLV: TWA 2 mg(Al)/m3

Diisobutylaluminium hydride Specification

The Diisobutylaluminium hydride, with the CAS registry number 1191-15-7, is also known as Hydrobis(2-methylpropyl)aluminum. It belongs to the product categories of Organometallics; Al (Alminum) Compounds; Biochemistry; Classes of Metal Compounds; Reagents for Oligosaccharide Synthesis; Reduction; Synthetic Organic Chemistry; Typical Metal Compounds; Metal alkyl. Its EINECS number is 214-729-9. This chemical's molecular formula is C8H19Al and molecular weight is 142.22. What's more, its systematic name is hydrido[bis(2-methylpropyl)]aluminum. It should be sealed and stored at the temperature of 2 - 8 °C. Moreover, it should be protected from oxides, heat and fire. It is a prostaglandin reducing agent. It is mainly used as reducing agent and hydrogen aluminum agent in the fine chemicals. It is useful in organic synthesis for a variety of reductions, including converting esters and nitriles to aldehydes.

Preparation of Diisobutylaluminium hydride:
Diisobutylaluminium hydride can be prepared by by thermal decomposition in the reduced pressure and at the temperature of 120- 180 °C with triisobutyl aluminium as raw materials. The yield is up to 95%.

Uses of Diisobutylaluminium hydride:
It can be used to produce O2,O3;O5,O6-diisopropyliden-1,4-anhydro-D-mannitol at the temperature of 0 °C. It will need solvent toluene with the reaction time of 10 min. The yield is about 71%.
Diisobutylaluminium hydride can be used to produce O2,O3;O5,O6-diisopropyliden-1,4-anhydro-D-mannitol at the temperature of 0 °C

When you are using Diisobutylaluminium hydride, please be cautious about it as the following:
Diisobutylaluminium hydride is harmful by inhalation, in contact with skin and if swallowed. If swallowed, it will not induce vomiting that you need seek medical advice immediately and show this container or label. It is harmful as it may cause lung damage if swallowed and has a danger of serious damage to health by prolonged exposure through inhalation. This chemical is toxic by inhalation, in contact with skin and if swallowed. Moreover, it is toxic to aquatic organisms as it may cause long-term adverse effects in the aquatic environment. The substance will react violently with water, liberating extremely flammable gases. Its vapours may cause drowsiness and dizziness. This chemical is spontaneously flammable in air and may form explosive peroxides. It can cause severe burns. It has a limited evidence of a carcinogenic effect and has a possible risk of harm to the unborn child and a possible risk of impaired fertility. This chemical is highly flammable, so you should keep it away from sources of ignition - No smoking. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you need wear suitable protective clothing, gloves and eye/face protection. You must take off immediately all contaminated clothing. You should not empty it into drains. In case of accident or if you feel unwell, you must seek medical advice immediately (show the label where possible). You should avoid releasing it to the environment just refering to special instructions/safety data sheet.

You can still convert the following datas into molecular structure:
(1)SMILES: CC(C)C[AlH]CC(C)C
(2)Std. InChI:InChI=1S/2C4H9.Al.H/c2*1-4(2)3;;/h2*4H,1H2,2-3H3;
(3)Std. InChIKey: AZWXAPCAJCYGIA-UHFFFAOYSA-N

The toxicity data of Diisobutylaluminium hydride is as follows:  

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LCLo inhalation 70gm/m3/1H (70000mg/m3) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES Medicina del Lavoro. Industrial Medicine. Vol. 57, Pg. 188, 1966.

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