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Sigma-Aldrich

n-Butyllithium solution

2.5 M in hexanes

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Synonym(s):
n-BuLi, Butyl lithium, Butyllithium solution, Lithium-1-butanide
Linear Formula:
CH3(CH2)3Li
CAS Number:
Molecular Weight:
64.06
Beilstein:
1209227
MDL number:
PubChem Substance ID:
NACRES:
NA.22

form

liquid

Quality Level

concentration

2.5 M in hexanes

density

0.693 g/mL at 25 °C

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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This Item
20159302120230715
concentration

2.5 M in hexanes

concentration

2.7 M in heptane

concentration

2.0 M in cyclohexane

concentration

11.0 M in hexanes

density

0.693 g/mL at 25 °C

density

0.71 g/mL at 20 °C

density

0.775 g/mL at 25 °C

density

0.761 g/mL at 25 °C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

100

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

Packaging

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

Legal Information

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

Signal Word

Danger

Hazard Classifications

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

Target Organs

Central nervous system

Supplementary Hazards

Storage Class Code

4.2 - Pyrophoric and self-heating hazardous materials

WGK

WGK 3

Flash Point(F)

-7.6 °F - closed cup

Flash Point(C)

-22 °C - closed cup


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Winter AM, et al.
Journal of Organometallic Chemistry, 682(1-2), 149-154 (2003)
n-Butyllithium
Ovaska TV, et al.
eEROS (Encyclopedia of Reagents for Organic Synthesis) (2001)
Microstructure-thermal property relationship of high trans-1, 4-poly (butadiene) produced by anionic polymerization of 1, 3-butadiene using an initiator composed of alkyl aluminum, n-butyl lithium, and barium alkoxide
Benvenuta-Tapia JJ, et al.
Polym. Eng. Sci., 49(1), 1-10 (2009)
Graeme Barker et al.
Organic letters, 12(18), 4176-4179 (2010-08-20)
A diamine-free protocol for the s-BuLi-mediated lithiation-trapping of N-Boc heterocycles has been developed. In the optimized procedure, lithiation is accomplished using s-BuLi in THF at -30 °C for only 5 or 10 min. Subsequent electrophilic trapping or transmetalation-Negishi coupling delivered
Lawrence M Pratt et al.
The Journal of organic chemistry, 68(16), 6387-6391 (2003-08-05)
The effects of lithium dialkylamide structure, mixed aggregate formation, and solvation on the stereoselectivity of ketone enolization were examined. Of the lithium dialkylamides examined, lithium tetramethylpiperidide (LiTMP) in THF resulted in the best enolization selectivity. The stereoselectivity was further improved

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