197343

Sigma-Aldrich

Methyllithium solution

1.6 M in diethyl ether

Synonym(s):
Lithium methanide, MeLi
Empirical Formula (Hill Notation):
CH3Li
CAS Number:
Molecular Weight:
21.98
Beilstein/REAXYS Number:
3587162
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

vapor density

3 (vs air)

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

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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

1 L in Sure/Seal™
8, 18 L in Kilo-Lab™
4×25, 50, 100, 4×100, 800 mL in Sure/Seal™
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

Signal Word

Danger

Supp Hazards

EUH019 - EUH066

RIDADR

UN 3394 4.3(4.2) / PGI

WGK Germany

WGK 1

Flash Point(F)

1.4 °F - closed cup

Flash Point(C)

-17 °C - closed cup

Certificate of Analysis
Certificate of Origin
A Simplified Approach with 3D Visuals
Vasishta Bhatt
Essentials of Coordination Chemistry: A Simplified Approach with 3D Visuals, 183-183 (2015)
Enantioselective addition of organolithium reagents to 3, 4-dihydroisoquinoline in the presence of (?)-sparteine as an external ligand. Application for the synthesis of isoquinoline alkaloids.
Chrzanowska M
Tetrahedron Asymmetry, 12(10), 1435-1440 (2001)
Kiran Kumar Solingapuram Sai et al.
Applied radiation and isotopes : including data, instrumentation and methods for use in agriculture, industry and medicine, 129, 57-61 (2017-08-15)
We automated radiochemical synthesis of 1-[
Cu-catalyzed enantioselective allylic alkylation with organolithium reagents.
Hornillos V, et al.
Nature Protocols, 12(3), 493-493 (2017)
T Jurca et al.
Dalton transactions (Cambridge, England : 2003), 46(4), 1172-1178 (2017-01-06)
The synthesis of molybdenum oxo-amidinate complexes MoO

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