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:
Molecular Weight:
105.94
UNSPSC Code:
12352302
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
4151240
Form:
liquid
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
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
Legal Information
Super-Hydride is a registered trademark of Merck KGaA, Darmstadt, Germany
signalword
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
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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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
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 179728-100ML | 04061838754417 |
| 179728-800ML | 04061838754424 |
| 179728-2L | 04061838118370 |
| 179728-18L-C | 04061838230737 |
| 179728-8L | 04061838125286 |
| 179728-4X25ML | 04065268444467 |