230715

Sigma-Aldrich

n-Butyllithium solution

11.0 M in hexanes

Sinónimos:
Butyl lithium, Lithium-1-butanide, Butyllithium solution, n-BuLi
Fórmula lineal:
CH3(CH2)3Li
Número de CAS:
Peso molecular:
64.06
Beilstein/REAXYS Number:
1209227
MDL number:
PubChem Substance ID:
NACRES:
NA.22

form

liquid

Quality Level

concentration

11.0 M in hexanes

density

0.761 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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General description

n-Butyllithium (n-BuLi) is an organolithium reagent commonly 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 reacting in situ with alkyl halides to obtain useful organic compounds by the formation of the C-C bond.

Application

n-BuLi can be used as a reagent for lithium-halogen exchange reactions. Synthesis of various other useful reagents such as lithium diisopropylamide (LDA) and diphenylphosphine is prepared by in situ reaction with n-BuLi . In the polymerization of dienes, it can be employed as an initiator.

Packaging

4×25, 100 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.

Legal Information

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

signalword

Danger

hazcat

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

Target Organs

Central nervous system, Nervous system

Supp Hazards

EUH014

storage_class_code

4.2 - Pyrophoric and self-heating hazardous materials

WGK Germany

WGK 2

Flash Point F

-7.6 °F - closed cup

Flash Point C

-22 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificado de Análisis

Certificado de origen

Diphenylphosphine.
Bianco, VD et al.
Inorganic Syntheses, 16(10), 161-163 (1976)
Rhodium pincer complexes of 2, 2?-bis (diphenylphosphino) diphenylamine
Winter AM, et al.
Journal of Organometallic Chemistry, 682(1-2), 149-154 (2003)
n-Butyllithium
Ovaska TV, et al.
Encyclopedia of Reagents for Organic Synthesis, Second Edition (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)
n-Butyllithium.
eEROS (Encyclopedia of Reagents for Organic Synthesis) (2001)

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