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241814

Sigma-Aldrich

Lithium tri-tert-butoxyaluminum hydride solution

1.0 M in THF

Synonym(s):

LTTBA, Lithium hydrotri-tert-butoxyaluminate, Tri-tert-butoxyaluminumlithium hydride

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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
MDL number:
MFCD00011532
UNSPSC Code:
12352000
PubChem Substance ID:
24854332
NACRES:
NA.22

form

liquid

reaction suitability

reagent type: reductant

concentration

1.0 M in THF

density

0.904 g/mL at 25 °C

SMILES string

[Li+].CC(C)(C)O[AlH-](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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General description

Lithium tri-tert-butoxyaluminum hydride is a mild reducing agent mainly used for the selective reduction of ketones.

Application

  • Reducing agent

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Oral - Carc. 2 - Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1B - STOT SE 3 - Water-react 1

Target Organs

Respiratory system

Supplementary Hazards

EUH014,EUH019

Storage Class Code

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

WGK

WGK 1

Flash Point(F)

1.4 °F - closed cup

Flash Point(C)

-17 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Synthesis of an enantiomerically pure intermediate containing the CD substructure of taxol.
Isaacs RC, et al.
The Journal of Organic Chemistry, 58(15), 3938-3941 (1993)
Synthesis of an Anti???Amino Epoxide by One?Carbon Homologation of an ??Amino Ester:(2S, 3S)?1, 2?Epoxy?3?(Boc?Amino)?4?Phenylbutane.
Wang D & Nugent WA
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The use of 4, 4-disubstituted nopinones for natural-product synthesis. Synthesis of elemanoid sesquiterpenes.
Kato M, et al.
The Journal of Organic Chemistry, 56(25), 7071-7076 (1991)
Stereoselectivity of lithium tri-tert-butoxyaluminum hydride.
Ashby EC, et al.
The Journal of Organic Chemistry, 36(1), 197-199 (1971)
M Gobbini et al.
Bioorganic & medicinal chemistry, 6(10), 1889-1894 (1998-12-05)
The four stereoisomers of the 2-hydroxy derivatives of digitoxigenin and 3-epidigitoxigenin have been synthesized, their structures established by NMR, and their binding affinity for the digitalis receptor on Na+, K(+)-ATPase evaluated. These derivatives showed lower affinities than the parent compounds.

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