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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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

PRTR

Class I Designated Chemical Substances

FSL

Group 3: Spontaneously combustible substances and water- reactive materials
Materials containing Organometallic compounds
Hazardous rank II
2nd spontaneously combustible materials and water reactive materials

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

178497-100ML:4548173109855
178497-18L-C:
178497-PZ:
178497-8L:4548173109886
178497-100L:
178497-18L:4548173109862
178497-BULK:
178497-VAR:
178497-90L:4548173249742
178497-800ML:4548173109879
178497-200L:4548173249735
178497-18L-KL:
178497-20L:

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Certificates of Analysis (COA)

Lot/Batch Number
SHBJ6879
SHBJ4403
SHBD6189V
63296DKV
46896KKV

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Li JJ, et al.
Modern Organic Synthesis in the Laboratory (2007)
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)
Lithium Tri-sec-butylborohydride
Hubbard JL and Dake G.
e-EROS Encyclopedia of Reagents for Organic Synthesis. (2012)
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)

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