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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:
Molecular Weight:
105.94
Beilstein:
4151240
MDL number:
UNSPSC Code:
12352302
PubChem Substance ID:
NACRES:
NA.22
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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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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.[1][2]

Application

LiTEBH can be used as a reagent:
  • To reduce alkyl halides to alkanes via dehydrogenation reactions.[1][3]
  • For the selective reduction of epoxides to Markovnikov alcohols.[4]
  • To reduce tosylates or mesylates primary alcohols to hydrocarbons.[1]
  • For reductive cyclization reactions for the preparation of useful intermediates.[5]
  • 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.[6]
  • For hydrodefluorination of C-F bonds using Ni catalyst.[1]
  • To prepare alkynyl alcohols from cleavage of cyclic keto-vinyl triflates.[7]
  • In the stereoselective reduction of bicyclic imides,[8] isoquinolines, and pyridines.[9]
  • To prepare tungsten and molybdenum hydride complexes.[10]

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

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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Customers Also Viewed

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
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)
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)

Questions

1–3 of 3 Questions  
  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  3. 超水素化溶液のの購入を検討しています。25MLx4本入りパッケージについて、試料容器はどのようになっているか教えていただけますでしょうか。具体的には、試料容器の形態(アンプル、蓋つき瓶等)、サイズについての情報が知りたいです。よろしくお願い足します。

    1 answer
    1. The 25 mL size is packaged in 35 mL narrow mouth amber glass bottle with a PTFE lined Red Polypropylene cap. Please see the representative image below.

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