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Sigma-Aldrich

Methyllithium solution

1.6 M in diethyl ether

Sinônimo(s):

Lithium methanide, MeLi

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About This Item

Fórmula empírica (Notação de Hill):
CH3Li
Número CAS:
917-54-4
Peso molecular:
21.98
Beilstein:
3587162
Número MDL:
MFCD00008253
Código UNSPSC:
12352103
ID de substância PubChem:
24851824
NACRES:
NA.22

densidade de vapor

3 (vs air)

Nível de qualidade

100

forma

liquid

composição

halide, ~0.05 M

concentração

1.6 M in diethyl ether

densidade

0.732 g/mL at 25 °C

temperatura de armazenamento

2-8°C

cadeia de caracteres SMILES

[Li]C

InChI

1S/CH3.Li/h1H3;

chave InChI

DVSDBMFJEQPWNO-UHFFFAOYSA-N

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Descrição geral

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.

Aplicação

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.

Embalagem

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

Informações legais

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

Palavra indicadora

Danger

Classificações de perigo

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

Perigos de suplementos

EUH019,EUH066

Código de classe de armazenamento

4.2 - Pyrophoric and self-heating hazardous materials

Classe de risco de água (WGK)

WGK 1

Ponto de fulgor (°F)

1.4 °F - closed cup

Ponto de fulgor (°C)

-17 °C - closed cup

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Certificados de análise (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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Artigos

Reagents for C–C Bond Formation

We carry a large variety of electrophiles and nucleophiles that are widely used in C–C bond-forming reactions. This group of products contains many organometallic reagents as well as commonly-used alkylating and acylating reagents.

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