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179728

Sigma-Aldrich

Super-Hydride® solution

1.0 M lithium triethylborohydride in THF

Synonym(s):

Lithium triethylborohydride solution

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About This Item

Linear Formula:
Li(C2H5)3BH
CAS Number:
22560-16-3
Molecular Weight:
105.94
Beilstein:
4151240
MDL number:
MFCD00011703
UNSPSC Code:
12352302
PubChem Substance ID:
24850649
NACRES:
NA.22

form

liquid

Quality Level

200

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

View returnable container options.

Legal Information

Super-Hydride is a registered trademark of Merck KGaA, Darmstadt, Germany

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

PRTR

Class I Designated Chemical Substances

FSL

Group 4: Flammable liquids
Type 1 petroleums
Hazardous rank II
Water insoluble liquid

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

179728-VAR:
179728-18L-C:
179728-20L:
179728-90L:4548173249889
179728-BULK:
179728-100L:
179728-8L:4548173110592
179728-2L:
179728-PZ:
179728-200L:4548173249872
179728-800ML:4548173110585
179728-4X25ML:4548173372129
179728-100ML:4548173110561
179728-18L:4548173110578

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Certificates of Analysis (COA)

Lot/Batch Number
0000324354
0000324354
SHBP1665
0000143566
SHBN6965

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Sci. Synth., 2, 13-89 (2003)
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)
Synthesis of the first per (3-deoxy)-cyclooligosaccharide: hepta (manno-3-deoxy-6-Ot-butyldimethylsilyl)-β-cyclodextrin
Kelly DR and Mishal AK
Tetrahedron Asymmetry, 10(18), 3627-3648 (1999)
Reduction of isoquinoline and pyridine-containing heterocycles with lithium triethylborohydride (Super-Hydride)
Blough BE and Carroll FI
Tetrahedron Letters, 34(45), 7239-7242 (1993)
Regio-and stereoselective reduction of bicyclic imides for the asymmetric synthesis of highly substituted pyrrolidines
Deprez P, et al.
Tetrahedron, 49(18), 3781-3792 (1993)
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