230707
n-Butyllithium solution
2.5 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:
Molecular Weight:
64.06
UNSPSC Code:
12352103
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
1209227
Concentration:
2.5 M in hexanes
Form:
liquid
form
liquid
Quality Level
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
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:
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.
Legal Information
Sure/Seal is a trademark of Sigma-Aldrich Co. LLC
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Danger
target_organs
Central nervous system
supp_hazards
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
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
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n-Butyllithium
Ovaska TV, et al.
eEROS (Encyclopedia of Reagents for Organic Synthesis) (2001)
Rhodium pincer complexes of 2, 2?-bis (diphenylphosphino) diphenylamine
Winter AM, et al.
Journal of Organometallic Chemistry, 682(1-2), 149-154 (2003)
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)