939412

n-Butyllithium solution

2.5 M (in PAO/hexanes mixture)

• Synonym(s): n-BuLi, Butyl lithium, Butyllithium solution, Lithium-1-butanide, n-BuLi
• Linear Formula: CH₃(CH₂)₃Li
• CAS Number: 109-72-8
• Molecular Weight: 64.06
• Beilstein: 1209227
• MDL number: MFCD00009414
• UNSPSC Code: 12352142

Properties

• form: liquid
• Quality Level: 100
• concentration: 2.5 M (in PAO/hexanes mixture)
• color: colorless to yellow
• storage temp.: 2-8°C
• SMILES string: [Li]CCCC
• InChI: 1S/C4H9.Li/c1-3-4-2;/h1,3-4H2,2H3;
• InChI key: MZRVEZGGRBJDDB-UHFFFAOYSA-N

Description

General description

n-Butyllithium (n-BuLi) is an organolithium reagent commonly used as a strong base in organic synthesis. It is also used as a lithium source for a wide range of lithium bases, such as lithium amides, acetylides, and alkoxides.

Application

n-BuLi can be used as a strong base to form corresponding lithium salts by the deprotonation of nitrogen, oxygen, phosphorus, and carbon acids. Heterocyclic compounds, such as furans, thiophenes, oxazoles, pyrroles, etc, can be lithiated α to the ring heteroatom using n-BuLi. These lithiated salts react in situ with alkyl halides to obtain useful organic compounds by the formation of the C-C bond. n-BuLi is also a useful reagent for lithium–halogen exchange reactions. Synthesis of various other useful reagents such as lithium diisopropylamide (LDA) and diphenylphosphine is done by in situ reaction with n-BuLi In the polymerization of dienes, n-BuLi is employed as an initiator.




The product is also used in the following reactions:

• Anionic rearrangement reactions
  
• Metal-halogen interchange and transmetalation reactions
• Elimination reactions
• [1,2]- and [1,4]-Wittig rearrangement reaction
• Anionic homo-Fries rearrangement reaction
• Asymmetric carbolithiation

Features and Benefits

This product is formulated in a solution of polyalphaolefin (PAO) and hexanes to prevent pyrophoric reactions when exposed to air, affording improved safety and usability.