468568

Hexyllithium solution

2.3 M in hexane

• Synonym(s): 1-Hexyllithium, n-Hexyllithium, Hexane - lithium complex
• Linear Formula: CH₃(CH₂)₅Li
• CAS Number: 21369-64-2
• Molecular Weight: 92.11
• Beilstein: 3600261
• MDL number: MFCD00191446
• UNSPSC Code: 12352103
• PubChem Substance ID: 24870524
• NACRES: NA.22

Properties

• Quality Level: 200
• concentration: 2.3 M in hexane
• bp: 69 °C
• density: 0.708 g/mL at 25 °C
• storage temp.: 2-8°C
• SMILES string: [Li]CCCCCC
• InChI: 1S/C6H13.Li/c1-3-5-6-4-2;/h1,3-6H2,2H3;
• InChI key: RMKNFFPDYCVCDI-UHFFFAOYSA-N

Description

General description

Hexyllithium solution is an organolithium compound used in organic synthesis as a strong base, alkylating agent, and lithiation reagent.

Application

Hexyllithium solution can be used as an alkylating agent in the:

• Ni-catalyzed cross-coupling with aryl halides.
• Cu-catalyzed enantioselective allylic alkylation.

It can also be used as a lithiation agent for the lithiation of azetidines.

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,GHS08,GHS05,GHS07,GHS09
• Signal Word: Danger
• Hazard Statements: H225,H250,H260,H304,H314,H336,H361f,H373,H411
• Precautionary Statements: 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. 1A - 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 3
• Flash Point(F): 15.8 °F - closed cup
• Flash Point(C): -9 °C - closed cup
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves