230715

n-Butyllithium solution

11.0 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: 1209227
• MDL number: MFCD00009414
• PubChem Substance ID: 24853833
• NACRES: NA.22

Properties

• form: liquid
• Quality Level: 100
• concentration: 11.0 M in hexanes
• density: 0.761 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 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 reacting in situ with alkyl halides to obtain useful organic compounds by the formation of the C-C bond.

Application

n-BuLi can be used as a reagent for lithium-halogen exchange reactions. Synthesis of various other useful reagents such as lithium diisopropylamide (LDA) and diphenylphosphine is prepared by in situ reaction with n-BuLi . In the polymerization of dienes, it can be employed as an initiator.

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

Safety Information

• Pictograms: GHS02,GHS05,GHS07,GHS08,GHS09
• Signal Word: Danger
• Hazard Statements: H225 - H250 - H260 - H304 - H314 - H336 - H361f - H373 - H411
• Precautionary Statements: P210 - P231 + P232 - P280 - P301 + P310 + P331 - P301 + P330 + P331 - P303 + P361 + P353 - P305 + P351 + P338 + P310 - 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 RE 2 Inhalation - STOT SE 3 - Water-react 1
• Target Organs: Central nervous system, Nervous system
• Supplementary Hazards: EUH014
• Storage Class Code: 4.2 - Pyrophoric and self-heating hazardous materials
• WGK: WGK 2
• Flash Point(F): -7.6 °F - closed cup
• Flash Point(C): -22 °C - closed cup
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves