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Merck
CN

230715

n-Butyllithium solution

11.0 M in hexanes

Synonym(s):

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

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About This Item

Linear Formula:
CH3(CH2)3Li
CAS Number:
109-72-8
Molecular Weight:
64.06
UNSPSC Code:
12352103
NACRES:
NA.22
PubChem Substance ID:
24853833
MDL number:
MFCD00009414
Beilstein/REAXYS Number:
1209227

Key Documents

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Product Name

n-Butyllithium solution, 11.0 M in hexanes

InChI

1S/C4H9.Li/c1-3-4-2;/h1,3-4H2,2H3;

SMILES string

[Li]CCCC

InChI key

MZRVEZGGRBJDDB-UHFFFAOYSA-N

form

liquid

concentration

11.0 M in hexanes

density

0.761 g/mL at 25 °C

storage temp.

2-8°C

Quality Level

100

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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.

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.

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

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Danger

Hazard Classifications

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

target_organs

Central nervous system, Nervous system

supp_hazards

EUH014

Storage Class

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

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
SHBT4394
SDBB2894
SDBB3717
SHBS0026
STBL0917

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n-Butyllithium
Ovaska TV, et al.
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2001)
Diphenylphosphine.
Bianco, VD et al.
Inorganic Syntheses, 16(10), 161-163 (1976)
Preparation, Properties, and Safe Handling of Commercial Organolithiums: Alkyllithiums, Lithium sec-Organoamides, and Lithium Alkoxides.
Rathman, Terry `Li? and Schwindeman, James A
Organic Process Research & Development, 18(10), 1192-1210 (2014)
n-Butyllithium.
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)
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Articles

Selective Metalation and Additions

Transformative reagents enable selective conversions within molecules containing sensitive functionalities under mild reactions.

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