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Fórmula lineal:
CH3(CH2)3Li
Número CAS:
Peso molecular:
64.06
UNSPSC Code:
12352103
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
1209227
Concentration:
2.0 M in cyclohexane
Form:
liquid
Servicio técnico
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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
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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Danger
target_organs
Central nervous system
supp_hazards
Clase de almacenamiento
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
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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)
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)
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)




