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Merck
CN

179728

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
UNSPSC Code:
12352302
NACRES:
NA.22
PubChem Substance ID:
24850649
MDL number:
MFCD00011703
Beilstein/REAXYS Number:
4151240
Form:
liquid

Key Documents

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InChI

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

SMILES string

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

InChI key

WCJAYABJWDIZAJ-UHFFFAOYSA-N

form

liquid

reaction suitability

reagent type: reductant

concentration

1.0 M lithium triethylborohydride in THF

density

0.892 g/mL at 25 °C

Quality Level

200

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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

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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

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

Regulatory Information

危险化学品
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Certificates of Analysis (COA)

Lot/Batch Number
0000427347
0000427347
0000324354
0000324354
0000143566

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Reduction of isoquinoline and pyridine-containing heterocycles with lithium triethylborohydride (Super-Hydride)
Blough BE and Carroll FI
Tetrahedron Letters, 34(45), 7239-7242 (1993)
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)
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)
Sci. Synth., 2, 13-89 (2003)
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)
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