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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:
4151240
MDL number:
PubChem Substance ID:
NACRES:
NA.22

form

liquid

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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This Item
703508214965214973
form

liquid

form

liquid

form

liquid

form

liquid

reaction suitability

reagent type: reductant

reaction suitability

reagent type: reductant

reaction suitability

reagent type: reductant

reaction suitability

reagent type: reductant

density

0.892 g/mL at 25 °C

density

0.883 g/mL at 25 °C

density

0.731 g/mL at 25 °C

density

1.23 g/mL at 25 °C

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

concentration

1.0 M lithium triethylborohydride in THF

concentration

10 % (w/w), 2.3 M in 2-methyltetrahydrofuran

concentration

1.0 M in heptane

concentration

1.0 M in methylene chloride

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.

Legal Information

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

Signal Word

Danger

Hazard Classifications

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

Supplementary Hazards

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

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