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
Regulatory Information
危险化学品
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Articles
Transformative reagents enable selective conversions within molecules containing sensitive functionalities under mild reactions.
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.
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
Lawrence M Pratt et al.
The Journal of organic chemistry, 68(16), 6387-6391 (2003-08-05)
The effects of lithium dialkylamide structure, mixed aggregate formation, and solvation on the stereoselectivity of ketone enolization were examined. Of the lithium dialkylamides examined, lithium tetramethylpiperidide (LiTMP) in THF resulted in the best enolization selectivity. The stereoselectivity was further improved
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 230707-800ML | 04061837880711 |
| 230707-PZ | 04061826597293 |
| 230707-100ML | 04061837880667 |
| 230707-18L-C | 04061837880674 |
| 230707-18L-KL | 04061837880681 |
| 230707-20L | 04061837880698 |
| 230707-4X100ML | 04061838782854 |
| 230707-4X25ML | 04061837880704 |
| 230707-8L | 04061837880728 |