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Sigma-Aldrich

n-Butyllithium solution

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2.5 M (in PAO/hexanes mixture)

Synonym(s):

Butyllithium solution, Lithium-1-butanide, n-BuLi, Butyl lithium

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About This Item

Linear Formula:
CH3(CH2)3Li
CAS Number:
Molecular Weight:
64.06
Beilstein:
1209227
MDL number:
UNSPSC Code:
12352142

form

liquid

Quality Level

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

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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.

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Description
Pricing

Signal Word

Danger

Hazard Classifications

Aquatic Chronic 3 - Asp. Tox. 1 - Eye Dam. 1 - Flam. Liq. 3 - Pyr. Liq. 1 - Repr. 2 - Skin Corr. 1B - STOT RE 2 Inhalation - Water-react 1

Target Organs

Nervous system

Supplementary Hazards

Storage Class Code

4.2 - Pyrophoric and self-heating hazardous materials

WGK

WGK 3

Flash Point(F)

88.7 °F

Flash Point(C)

31.5 °C


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