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Key Documents

178497

Sigma-Aldrich

L-Selectride® solution

1.0 M in THF

Synonym(s):

Lithium tri-sec-butylborohydride solution

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About This Item

Linear Formula:
Li[CH(CH3)CH2CH3]3BH
CAS Number:
Molecular Weight:
190.10
Beilstein:
4007327
MDL number:
UNSPSC Code:
12352000
PubChem Substance ID:
NACRES:
NA.22

form

liquid

Quality Level

reaction suitability

reagent type: reductant

concentration

1.0 M in THF

density

0.89 g/mL at 25 °C

SMILES string

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

InChI

1S/C12H28B.Li/c1-7-10(4)13(11(5)8-2)12(6)9-3;/h10-13H,7-9H2,1-6H3;/q-1;+1

InChI key

ACJKNTZKEFMEAK-UHFFFAOYSA-N

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General description

L-Selectride® is an air and water sensitive solution mainly used as a bulky stereoselective hydride reducing agent.

Application

L-Selectride solution may be used in the O-demethylation and N-demethylation of opium alkaloids and their derivatives.
L-Selectride® can be used as a reagent for:
  • The stereoselective reduction of ketone to alcohol.
  • The selective demethylation of tert alcohol.

  • Reducing agent

Reagent for:
  • Enantioselective synthesis of a-amino acids via reduction of N-tert-butanesulfinyl ketimine esters
  • Diastereoselective reduction reactions
  • Hydride reduction of the Danishefsky pyranones
  • Asymmetric reductive aldol reaction of enones with a-alkoxy aldehydes
  • Synthesis of alkanols by carbonylation reactions

Legal Information

6538 is a trademark of American Type Culture Collection
Selectride is a registered trademark of Merck KGaA, Darmstadt, Germany

Signal Word

Danger

Hazard Classifications

Carc. 2 - Flam. Liq. 2 - Pyr. Liq. 1 - Skin Corr. 1B - STOT SE 3 - Water-react 1

Target Organs

Respiratory system

Supplementary Hazards

Storage Class Code

4.2 - Pyrophoric and self-heating hazardous materials

WGK

WGK 3

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

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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