197343

Methyllithium solution

1.6 M in diethyl ether

• Synonym(s): Lithium methanide, MeLi
• Empirical Formula (Hill Notation): CH₃Li
• CAS Number: 917-54-4
• Molecular Weight: 21.98
• Beilstein/REAXYS Number: 3587162
• MDL number: MFCD00008253
• UNSPSC Code: 12352103
• PubChem Substance ID: 24851824
• NACRES: NA.22

Properties

• vapor density: 3 (vs air)
• Quality Level: 100
• form: liquid
• composition: halide, ~0.05 M
• concentration: 1.6 M in diethyl ether
• density: 0.732 g/mL at 25 °C
• storage temp.: 2-8°C
• SMILES string: [Li]C
• InChI: 1S/CH3.Li/h1H3;
• InChI key: DVSDBMFJEQPWNO-UHFFFAOYSA-N

Description

General description

Methyllithium is an organolithium reagent mainly used for deprotonation and as a source of methyl anion. It is a strong base and a strong nucleophile.

Application

Methyllithium solution (1.6M in diethyl ether) has been used for the asymmetric allylic alkylation (AAA) of allylic electrophiles in the presence of a chiral copper catalyst. This protocol leads to the C-C bond formation of tertiary and quaternary stereogenic centers with high enantioselectivity. It can also be used for the synthesis of (−)-salsolidine by reacting with 6,7-dimethoxy-3,4-dihydroisoquinoline in the presence of (−)-sparteine as a chiral ligand.

Packaging

The 25 mL Sure/Seal^™ bottle is recommended as a single-use bottle. Repeated punctures will likely result in decreased performance of product.

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Legal Information

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

Safety Information

• pictograms: GHS02,GHS05,GHS07
• signalword: Danger
• hcodes: H225,H250,H260,H302,H314,H336
• pcodes: P210 - P222 - P223 - P231 + P232 - P370 + P378 - P422
• Hazard Classifications: Acute Tox. 4 Oral - Flam. Liq. 2 - Pyr. Liq. 1 - Skin Corr. 1B - STOT SE 3 - Water-react 1
• supp_hazards: EUH019,EUH066
• Storage Class: 4.2 - Pyrophoric and self-heating hazardous materials
• wgk_germany: WGK 1
• flash_point_f: 1.4 °F - closed cup
• flash_point_c: -17 °C - closed cup