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302120

n-Butyllithium solution

2.0 M in cyclohexane

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:
24858234
MDL number:
MFCD00009414
Beilstein/REAXYS Number:
1209227
Concentration:
2.0 M in cyclohexane
Form:
liquid
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form

liquid

Quality Level

200

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

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

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signalword

Danger

target_organs

Central nervous system

supp_hazards

EUH014

Storage Class

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

flash_point_f

-0.4 °F - closed cup

flash_point_c

-18 °C - closed cup

ppe

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

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

Regulatory Information

危险化学品

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Certificates of Analysis (COA)

Lot/Batch Number
SHBM6165
SHBM6164
SHBL9015
SHBL0397
SHBK9728

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Articles

Selective Metalation and Additions

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

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)
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)
View All Related Papers

Global Trade Item Number

SKUGTIN
302120-PZ04061823822282
302120-100ML04061837881015
302120-4X25ML04061826665725
302120-800ML04061837881022