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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/REAXYS Number:
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

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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

supp_hazards

EUH014,EUH019

Storage Class

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

wgk_germany

WGK 1

flash_point_f

1.4 °F - closed cup

flash_point_c

-17 °C - closed cup

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

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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Contreras L, et al.
Organometallics, 12(10), 4228-4228 (1993)
Lithium Triethylborohydride
Zaidlewicz M, et al.
Encyclopedia of Reagents for Organic Synthesis, Second Edition, 1-10 (2001)
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Chemical modification of paraherquamide. 1. Unusual reactions and absolute stereochemistry
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The Journal of Organic Chemistry, 54(11), 2657-2663 (1989)
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