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195596 Aldrich

sec-Butyllithium solution

1.4 M in cyclohexane

Synonym: Lithium-2-butanide, s-BuLi

  • CAS Number 598-30-1

  • Linear Formula CH3CH2CH(CH3)Li

  • Molecular Weight 64.06

  •  Beilstein Registry Number 3587206

  •  MDL number MFCD00009323

  •  PubChem Substance ID 24851700

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Properties

Related Categories 25mL Sure/Seal Reagents, Acids & Bases, Alkyl, Bases, Chemical Synthesis,
InChI Key   VATDYQWILMGLEW-UHFFFAOYSA-N
concentration   1.4 M in cyclohexane
density   0.769 g/mL at 25 °C
storage temp.   2-8°C

Description

Packaging

4×25, 50, 100, 800 mL in Sure/Seal™

The 25 mL Sure/Seal bottle is recommended as a single-use bottle. Repeated punctures will likely result in decreased performance of product.

Application

sec-Butyllithium solution (1.4M in cyclohexane) has been used in the multi-step synthesis of 5-methyl-5,6-dihydrothymidine (5-MDHT) from thymidine. It has also been used in the copper-catalyzed asymmetric allylic alkylation (AAA) of allyl bromides, chlorides, and ethers in the presence of a chiral ligand.

Legal Information

Sure/Seal is a trademark of Sigma-Aldrich Co. LLC

Safety & Documentation

Safety Information

Signal word 
Danger
Precautionary statements 
RIDADR 
UN3394 - class 4.2 - PG 1 - EHS - Organometallic substance, liquid, pyrophoric, water-reactive, HI: all (not BR)
WGK Germany 
2
Flash Point(F) 
1.4 °F
Flash Point(C) 
-17 °C

Documents

Certificate of Analysis

Certificate of Origin


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Protocols & Articles

Articles

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Acids and bases have been used by chemists for centuries, and are among the most fundamental reagents employed in synthetic organic chemistry. This Aldrich product line ranges from Brønsted and Lewis...
Chemfiles Volume 1 Article 3

MRT - Three-Stage Lithium-Organic Synthesis

Benefit from MRT & Flow Chemistry: cost & time savings, highly reliable synthesis protocol guaranteeing constant quality.
Matthias Junkers
Aldrich ChemFiles 2009, 9.4, 17.
Keywords: Continuous flow chemistry, Microreactor technology

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Enantioenriched chiral alkyl boronic esters are highly useful reagents that can be easily prepared and subsequently transformed into a variety of functional groups.1 To add to the arsenal of transfor...
Keywords: Alkynylations, Asymmetric synthesis, Deprotonations, Eliminations, Iodinations, Olefinations

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References

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