Lithium tri-tert-butoxyaluminum hydride Property

Melting point:

300-319 °C (dec.) (lit.)

Boiling point:

66°C (THF)

Density 

0.942 g/mL at 25 °C

Flash point:

95 °F

storage temp. 

2-8°C

solubility 

It is soluble in organic solvents at low temperatures.

form 

Solution

color 

Clear to slightly turbid colorless

Water Solubility 

Reacts with water.

Sensitive 

Air & Moisture Sensitive

BRN 

5796791

Exposure limits

ACGIH: TWA 50 ppm; STEL 100 ppm (Skin)
OSHA: TWA 200 ppm(590 mg/m3)
NIOSH: IDLH 2000 ppm; TWA 200 ppm(590 mg/m3); STEL 250 ppm(735 mg/m3)

Stability:

Stable. Incompatible with alcohols. Reacts violently with water. Highly flammable.

InChIKey

BYBIDFZFKATBFH-UHFFFAOYSA-N

CAS DataBase Reference

17476-04-9(CAS DataBase Reference)

EPA Substance Registry System

Aluminate(1-), hydrotris(2-methyl-2-propanolato)-, lithium, (T-4)- (17476-04-9)

Safety

Hazard Codes 

F,C,T

Risk Statements 

60-61-10-14/15-19-34-14-11-15-35-40-37

Safety Statements 

53-26-36/37/39-43-45-16-43B-6A

RIDADR 

UN 3399 4.3/PG 1

WGK Germany 

1

RTECS 

OJ5585000

F 

10-21

TSCA 

Yes

HazardClass 

4.3

PackingGroup 

II

HS Code 

29055900

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H260In contact with water releases flammable gases which may ignite spontaneously

H314Causes severe skin burns and eye damage

Precautionary statements

P223Keep away from any possible contact with water, because of violent reaction and possible flash fire.

P231+P232Handle under inert gas. Protect from moisture.

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Lithium tri-tert-butoxyaluminum hydride Chemical Properties,Usage,Production

Chemical Properties

Lithium tri-tert-butoxyaluminum hydride is a white powder with a melting point of 319°C, which is sublimated under vacuum at 280°C. It is soluble in ethylene glycol dimethyl ether, diglyme and tetrahydrofuran, and slightly soluble in ether. Stable in dry air, hydrolyzed slowly in moist air. Lithium tri-tert-butoxyaluminum hydride is a mild and highly selective reducing agent. Ketones, aldehydes and acid chlorides can be reduced in diethyl ether or diglyme at 0°C, fatty acid esters and nitriles are not reduced, but phenyl esters of fatty acids and alicyclic acids can be reduced.

Uses

antimicrobial, cholesterol lowering agent, for ion-permeable synthetic membranes

Uses

Lithium tri-tert-butoxyaluminum hydride is less reactive than lithium aluminum hydride (LAH) and is very useful in selective reductions of acyl halides, aldehydes, ketones, and esters. It is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dye stuff. LAH, is a reducing agent commonly employed in modern organic synthesis.

Preparation

Lithium aluminum hydride reacts with tert-butanol in ether to prepare Lithium tri-tert-butoxyaluminum hydride.
LiAlH4+3 (CH3)3COH→LiAlH[OC(CH3)3] 3+3 H2

General Description

Lithium tri-tert-butoxyaluminum hydride is a mild reducing agent mainly used for the selective reduction of ketones. It is very suitable for selective reductions on account of its mild reducing power, the most important of these being the reduction of steroid ketones. In addition to chemical selectivity, a certain stereoselectivity is shown in the reduction of cyclic ketones.

reaction suitability

reagent type: reductant