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197343

Sigma-Aldrich

Methyllithium solution

1.6 M in diethyl ether

Synonym(s):

Lithium methanide, MeLi

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About This Item

Empirical Formula (Hill Notation):
CH3Li
CAS Number:
917-54-4
Molecular Weight:
21.98
Beilstein:
3587162
MDL number:
MFCD00008253
UNSPSC Code:
12352103
PubChem Substance ID:
24851824
NACRES:
NA.22

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

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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

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

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Oral - Flam. Liq. 2 - Pyr. Liq. 1 - Skin Corr. 1B - STOT SE 3 - Water-react 1

Supplementary Hazards

EUH019,EUH066

Storage Class Code

4.2 - Pyrophoric and self-heating hazardous materials

WGK

WGK 1

Flash Point(F)

1.4 °F - closed cup

Flash Point(C)

-17 °C - closed cup

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Certificates of Analysis (COA)

Lot/Batch Number
STBK4962
SHBM2496
STBJ6141
SHBL4713
SHBL3856

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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-[
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)
A Simplified Approach with 3D Visuals
Vasishta Bhatt
Essentials of Coordination Chemistry: A Simplified Approach with 3D Visuals, 183-183 (2015)
Mingyang Zhang et al.
Macromolecular rapid communications, 41(18), e2000323-e2000323 (2020-08-11)
Carbon monoxide (CO) has emerged as a potential therapeutic agent for the treatment of many diseases. However, the therapeutic outcome is highly dependent on the dosages and administration sites. Hence, there is mounting interest in the development of CO-releasing materials
Cu-catalyzed enantioselective allylic alkylation with organolithium reagents.
Hornillos V, et al.
Nature Protocols, 12(3), 493-493 (2017)
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