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L2904

Sigma-Aldrich

Lithium tri-tert-butoxyaluminum hydride

97%

Synonym(s):

LTBA, Lithium aluminum-tri-tert-butoxyhydride

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About This Item

Linear Formula:
LiAlH[OC(CH3)3]3
CAS Number:
17476-04-9
Molecular Weight:
254.27
Beilstein:
5796791
EC Number:
241-490-8
MDL number:
MFCD00011532
UNSPSC Code:
12352000
PubChem Substance ID:
24896329
NACRES:
NA.22

Quality Level

100

Assay

97%

reaction suitability

reagent type: reductant

mp

300-319 °C (dec.) (lit.)

SMILES string

[H][Al]([Li])(OC(C)(C)C)(OC(C)(C)C)OC(C)(C)C

InChI

1S/3C4H9O.Al.Li.H/c3*1-4(2,3)5;;;/h3*1-3H3;;;/q3*-1;+2;+1;

InChI key

BYBIDFZFKATBFH-UHFFFAOYSA-N

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Application

  • Reducing agent
Lithium tri-tert-butoxyaluminum hydride (LTBA) is a stable, mild reducing agent that is used to selectively reduce aldehydes and ketones in the presence of esters. It can also be used to reduce imidoyl chlorides to aldimines and aromatic disulfides to the corresponding thiols.

Pictograms

FlameCorrosion
GHS02,GHS05

Signal Word

Danger

Hazard Statements

H260,H314

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B - Water-react 1

Supplementary Hazards

EUH014

Storage Class Code

4.3 - Hazardous materials which set free flammable gases upon contact with water

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SHBQ6520
SHBN9172
SHBJ6003
SHBJ3406
SHBG9725V

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Remarkably facile reductive opening of tetrahydrofuran and related ethers by lithium tri-tert-butoxyaluminohydride in the presence of triethylborane.
Brown H C, et al.
Journal of the American Chemical Society, 94(5), 1750-1751 (1972)
Rapid and selective reduction of functionalized aromatic disulfides with lithium tri-tert-butoxyaluminohydride. A remarkable steric and electronic control. Comparison of various hydride reagents.
Krishnamurthy S and Aimino D
The Journal of Organic Chemistry, 54(18), 4458-4462 (1989)
Electrolytic Decarboxylation. 6. A Convenient Synthesis of 3-(cis-3-Hexenyl)-2-cyclopentenone, a Precursor of cis-Jasmone Synthesis.
Torii S, et al.
Bulletin of the Chemical Society of Japan, 55(12), 3947-3948 (1982)
Facile preparation of polyfluoroalkylated aldimines from polyfluoroalkanoic acids.
Takagi J, et al.
Synthesis, 2007(11), 1624-1628 (2007)

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