179728

Sigma-Aldrich

Super-Hydride® solution

1.0 M lithium triethylborohydride in THF

Synonym(s):
Lithium triethylborohydride solution
Linear Formula:
Li(C2H5)3BH
CAS Number:
Molecular Weight:
105.94
Beilstein/REAXYS Number:
4151240
MDL number:
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

reaction suitability

reagent type: reductant

concentration

1.0 M lithium triethylborohydride in THF

density

0.892 g/mL at 25 °C

SMILES string

[Li+].[H][B-](CC)(CC)CC

InChI

1S/C6H16B.Li/c1-4-7(5-2)6-3;/h7H,4-6H2,1-3H3;/q-1;+1

InChI key

WCJAYABJWDIZAJ-UHFFFAOYSA-N

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General description

Super-Hydride® solution (Lithium triethylborohydride or LiTEBH) is widely used as a powerful and selective reducing agent that shows super hydride activity in organic synthesis.

Application

LiTEBH can be used as a reagent:
  • To reduce alkyl halides to alkanes via dehydrogenation reactions.
  • For the selective reduction of epoxides to Markovnikov alcohols.
  • To reduce tosylates or mesylates primary alcohols to hydrocarbons.
  • For reductive cyclization reactions for the preparation of useful intermediates.
  • In the synthesis of hepta(manno-3-deoxy-6-O-t-butyldimethylsilyl)-β-cyclodextrin by reduction of hepta(manno-2,3-anhydro-6-O-t-butyldimethylsilyl)-β-cyclodextrin.
  • For hydrodefluorination of C-F bonds using Ni catalyst.
  • To prepare alkynyl alcohols from cleavage of cyclic keto-vinyl triflates.
  • In the stereoselective reduction of bicyclic imides, isoquinolines, and pyridines.
  • To prepare tungsten and molybdenum hydride complexes.

Packaging

2 L in Sure/Seal™
8, 18 L in Kilo-Lab™
100, 800 mL in Sure/Seal™

Legal Information

Super-Hydride is a registered trademark of Sigma-Aldrich Co. LLC

Signal Word

Danger

Target Organs

Respiratory system

Supp Hazards

EUH014 - EUH019

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

UN 3399A 4.3(3) / PGI

WGK Germany

WGK 1

Flash Point(F)

1.4 °F - closed cup

Flash Point(C)

-17 °C - closed cup

Lithium Triethylborohydride
Zaidlewicz M, et al.
Encyclopedia of Reagents for Organic Synthesis, Second Edition, 1-10 (2001)
Seven-coordinate hydride complexes of molybdenum and tungsten. Crystal and molecular structures of WH(Cl)(CO)2(PMe3)3
Contreras L, et al.
Organometallics, 12(10), 4228-4228 (1993)
Shin Kamijo et al.
Journal of the American Chemical Society, 128(19), 6499-6507 (2006-05-11)
A thorough analysis of the chemistry of vinylogous acyl triflates provides insight into important chemical processes and opens new directions in synthetic technology. Tandem nucleophilic addition/C-C bond cleaving fragmentation reactions of cyclic vinylogous acyl triflates 1 yield a variety of...
Selective reductions. 32. Structural effects on the reduction of epoxides by lithium triethylborohydride. A kinetic study
Brown HC, et al.
The Journal of Organic Chemistry, 48(18), 3091-3096 (1983)
Reduction of isoquinoline and pyridine-containing heterocycles with lithium triethylborohydride (Super-Hydride)
Blough BE and Carroll FI
Tetrahedron Letters, 34(45), 7239-7242 (1993)

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