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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:
38721-52-7
Molecular Weight:
190.10
Beilstein:
4007327
MDL number:
MFCD00011708
UNSPSC Code:
12352000
PubChem Substance ID:
24850749
NACRES:
NA.22

form

liquid

Quality Level

200

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

Packaging

View returnable container options.

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

EUH019

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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Stereoselective synthesis of a novel pseudopeptide hapten for the generation of hydrolytic catalytic antibodies
Rodriguez AC, et al.
Tetrahedron Asymmetry, 15(12), 1847-1855 (2004)
L-Selectride as a General Reagent for the O-Demethylation and N-Decarbomethoxylation of Opium Alkaloids and Derivatives1.
Coop A, et al.
The Journal of Organic Chemistry, 63(13), 4392-4396 (1998)
A General and Simple Diastereoselective Reduction by L-Selectride: Efficient Synthesis of Protected (4S, 5S)-Dihydroxy Amides.
Yin B, et al.
Molecules (Basel), 15(4), 2771-2781 (2010)
Lithium Tri-sec-butylborohydride
Hubbard JL and Dake G.
e-EROS Encyclopedia of Reagents for Organic Synthesis. (2012)
Collective syntheses of icetexane Natural Products based on biogenetic hypotheses
Thommen C, et al.
Chemistry?A European Journal , 23(1), 120-127 (2017)
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