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302120

Sigma-Aldrich

n-Butyllithium solution

2.0 M in cyclohexane

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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/REAXYS Number:
1209227
MDL number:
PubChem Substance ID:
NACRES:
NA.22

form

liquid

Quality Level

concentration

2.0 M in cyclohexane

bp

80 °C

density

0.775 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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1 of 4

This Item
23070720159230715
vibrant-m

302120

n-Butyllithium solution

vibrant-m

230707

n-Butyllithium solution

vibrant-m

20159

n-Butyllithium solution

vibrant-m

230715

n-Butyllithium solution

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

100

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

form

liquid

form

liquid

form

liquid

form

liquid

density

0.775 g/mL at 25 °C

density

0.693 g/mL at 25 °C

density

0.71 g/mL at 20 °C

density

0.761 g/mL at 25 °C

bp

80 °C

bp

-

bp

-

bp

-

General description

n-Butyllithium (n-BuLi) is an organolithium reagent widely used as a strong base (superbase) in organic synthesis for the preparation of various chemical intermediates. It is also used as a reagent for lithium-halogen exchange and lithium-metal transmetalation reactions. n-BuLi is capable of lithiating carbon acids.

Application

n-Butyllithium (2.0 M in cyclohexane) can be used as:      
  • A polymerization initiator to synthesize polystyrenes by anionic polymerization of styrene.      
  • A strong base in the diastereoselective alkylation reactions.
  • A reagent to synthesize 2-benzoylpyrroles by reacting benzaldehydes with di(1H-pyrrol-1-yl)zirconium(IV) chloride complex.

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

signalword

Danger

Hazard Classifications

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

target_organs

Respiratory system

supp_hazards

Storage Class

4.3 - Hazardous materials, which set free flammable gases upon contact with water

wgk_germany

WGK 2

flash_point_f

-0.4 °F - closed cup

flash_point_c

-18 °C - closed cup

ppe

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


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Comparison of the synthetic utility of n-butyllithium and lithium diisopropylamide in the metalations of N, N-dialkyltoluamides.
Ludt RE, et al
The Journal of Organic Chemistry, 38(9), 1668-1674 (1973)
High-field proton NMR study of the aggregation and complexation of n-butyllithium in tetrahydrofuran.
McGarrity JF and Ogle CA.
Journal of the American Chemical Society, 107(7), 1805-1810 (1985)
Arene-metal complexes. 13. Reaction of substituted (benzene) tricarbonylchromium complexes with n-butyllithium.
Card RJ and Trahanovsky WS.
The Journal of Organic Chemistry, 45(13), 2560-2566 (1980)
Lithium intercalation via n-butyllithium of the layered transition metal dichalcogenides.
Dines MB.
Materials Research Bulletin, 10(4), 287-291 (1975)
Jennifer L Rutherford et al.
Journal of the American Chemical Society, 124(2), 264-271 (2002-01-10)
6Li and (13)C NMR spectroscopic studies were carried out on [(6)Li]n-BuLi and [(6)Li]PhLi (RLi) in toluene-d(8) containing the following diamines: N,N,N',N'-tetramethylethylenediamine (TMEDA), N,N,N',N'-tetraethylethylenediamine, 1,2-dipyrrolidinoethane, 1,2-dipiperidinoethane, N,N,N',N'-tetramethylpropanediamine, trans-(R,R)-N,N,N',N'-tetramethylcyclohexanediamine, and (-)-sparteine. Dimers of general structure (RLi)(2)S(2) (S = chelating diamine) are formed

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