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230707

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:
109-72-8
Molecular Weight:
64.06
Beilstein:
1209227
MDL number:
MFCD00009414
PubChem Substance ID:
24853832
NACRES:
NA.22

form

liquid

Quality Level

200

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
20159186171302120
n-Butyllithium solution 2.5 M in hexanes

Sigma-Aldrich

230707

n-Butyllithium solution

n-Butyllithium solution 2.7 M in heptane

Sigma-Aldrich

20159

n-Butyllithium solution

n-Butyllithium solution 1.6 M in hexanes

Sigma-Aldrich

186171

n-Butyllithium solution

n-Butyllithium solution 2.0 M in cyclohexane

Sigma-Aldrich

302120

n-Butyllithium solution

concentration

2.5 M in hexanes

concentration

2.7 M in heptane

concentration

1.6 M in hexanes

concentration

2.0 M in cyclohexane

density

0.693 g/mL at 25 °C

density

0.71 g/mL at 20 °C

density

0.68 g/mL at 25 °C

density

0.775 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

-

Quality Level

200

Quality Level

200

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.
View returnable container options.

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

Respiratory system

Supplementary Hazards

EUH014

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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Yuqiang Ma et al.
ACS nano, 9(7), 7383-7391 (2015-07-01)
Two-dimensional (2D) semiconducting monolayer transition metal dichalcogenides (TMDCs) have stimulated lots of interest because they are direct bandgap materials that have reasonably good mobility values. However, contact between most metals and semiconducting TMDCs like 2H phase WSe2 are highly resistive
Enantioselective total synthesis of the marine toxin (-)-gymnodimine employing a Barbier-type macrocyclization.
Ke Kong et al.
Angewandte Chemie (International ed. in English), 48(40), 7402-7405 (2009-09-04)
Deyu Li et al.
The Journal of organic chemistry, 73(6), 2373-2381 (2008-02-26)
A system consisting of a chiral lithium amide and n-BuLi in tol-d(8) solution was investigated with (1)H and (13)C INEPT DOSY, (6)Li and (15)N NMR, and other 2D NMR techniques. A mixed 2:1 trimeric complex was identified as the major
Michael A Tarselli et al.
Organic letters, 11(20), 4596-4599 (2009-10-09)
A procedure for the coupling of aliphatic imines with allylic and allenic alkoxides is described. The success of these studies was enabled by a unique reactivity profile of Ti(IV) isopropoxide/n-BuLi compared to well-known Ti(IV) isopropoxide/RMgX systems.
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
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