Skip to Content
Merck
All Photos(2)

Key Documents

View All Documentation

178497

Sigma-Aldrich

L-Selectride® solution

1.0 M in THF

Synonym(s):

Lithium tri-sec-butylborohydride solution

Sign Into View Organizational & Contract Pricing
All Photos(2)

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
Pricing and availability is not currently available.

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

Looking for similar products? Visit Product Comparison Guide

Related Categories

General description

L-Selectride® is an air and water sensitive solution[1] mainly used as a bulky stereoselective hydride reducing agent.[2]

Application

L-Selectride® can be used as a reagent for:
  • The stereoselective reduction of ketone to alcohol.[3]
  • The selective demethylation of tert alcohol.[4]

L-Selectride® solution may be used in the O-demethylation and N-demethylation of opium alkaloids and their derivatives.[5]
  • 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

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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
SHBJ6879
SHBJ4403
SHBD6189V
63296DKV
58397EJ

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Collective syntheses of icetexane Natural Products based on biogenetic hypotheses
Thommen C, et al.
Chemistry?A European Journal , 23(1), 120-127 (2017)
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)
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)
View All Related Papers

Questions

1–2 of 2 Questions  

  1. 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

      Helpful?

  2. 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

      Helpful?

Reviews

No rating value

Active Filters

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service