230707

n-Butyllithium solution

2.5 M in hexanes

• Synonym(s): n-BuLi, Butyl lithium, Butyllithium solution, Lithium-1-butanide
• Linear Formula: CH₃(CH₂)₃Li
• CAS Number: 109-72-8
• Molecular Weight: 64.06
• Beilstein/REAXYS Number: 1209227
• MDL number: MFCD00009414
• UNSPSC Code: 12352103
• PubChem Substance ID: 24853832
• NACRES: NA.22

Properties

• form: liquid
• Quality Level: 200
• 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

Description

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:      

• 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.

View returnable container options.

Legal Information

Sure/Seal is a trademark of Sigma-Aldrich Co. LLC

Safety Information

• pictograms: GHS02,GHS08,GHS05,GHS07,GHS09
• signalword: Danger
• hcodes: H225,H250,H260,H304,H314,H336,H361f,H411
• pcodes: P210 - P231 + P232 - P280 - P301 + P330 + P331 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338 - P370 + P378
• 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
• target_organs: Central nervous system
• supp_hazards: EUH014
• Storage Class: 4.2 - Pyrophoric and self-heating hazardous materials
• wgk_germany: WGK 3
• flash_point_f: -7.6 °F - closed cup
• flash_point_c: -22 °C - closed cup