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417246

Sigma-Aldrich

Dimethylzinc solution

1.0 M in heptane

Sinônimo(s):

Dimethylzinc

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About This Item

Fórmula linear:
(CH3)2Zn
Número CAS:
544-97-8
Peso molecular:
95.46
Beilstein:
3587195
Número MDL:
MFCD00014854
Código UNSPSC:
12352103
ID de substância PubChem:
24866132
NACRES:
NA.22

forma

liquid

Nível de qualidade

100

concentração

1.0 M in heptane

pb

44-46 °C

densidade

0.724 g/mL at 25 °C

cadeia de caracteres SMILES

C[Zn]C

InChI

1S/2CH3.Zn/h2*1H3;

chave InChI

AXAZMDOAUQTMOW-UHFFFAOYSA-N

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Descrição geral

Dimethylzinc (Zn(CH3)2) is a methylating reagent used to prepare methylated organic compounds as well as organometallic compounds containing methyl groups . It is also utilized as a reagent to prepare amino alcohols, oximes, and hydrazones from arylamines, alkoxyamines, and dialkylhydrazines respectively, by radical addition reaction in the presence of air and THF.

Dimethylzinc is a diorganozinc reagent and nucleophile used in the synthesis of propargylic amines.

Aplicação

Dimethylzinc solution can be used as:
  • A catalyst with nickel for the stereoselective C−2 alkenylation and dialkenylation of pyridine derivatives by alkynes to give monoalkenylation products.
  • A reagent with aldehydes and 2-methoxyaniline for the synthesis of enantioselective alkyl and aralkyl secondary amines via one-pot three-component coupling reaction in the presence of zirconium tetraisopropoxide.
  • A methylating reagent for methylation of fluoroalkylated pyruvates in the presence of copper/chiral diphosphine catalyst.

Palavra indicadora

Danger

Classificações de perigo

Aquatic Acute 1 - Aquatic Chronic 1 - Asp. Tox. 1 - Eye Dam. 1 - Flam. Liq. 2 - Pyr. Liq. 1 - Skin Corr. 1B - STOT SE 3 - Water-react 2

Órgãos-alvo

Central nervous system

Código de classe de armazenamento

4.2 - Pyrophoric and self-heating hazardous materials

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

30.2 °F - closed cup

Ponto de fulgor (°C)

-1 °C - closed cup

Equipamento de proteção individual

Faceshields, Gloves, Goggles

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Certificados de análise (COA)

Lot/Batch Number
SHBL2186
SHBJ4691
SHBH1126V
SHBF9286V
SHBD5977V

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Kohsuke Aikawa et al.
Beilstein journal of organic chemistry, 14, 576-582 (2018-04-07)
The catalytic asymmetric methylation of fluoroalkylated pyruvates is shown with dimethylzinc as a methylating reagent in the presence of a copper catalyst bearing a chiral phosphine ligand. This is the first catalytic asymmetric methylation to synthesize various α-fluoroalkylated tertiary alcohols
Formation of transient dimethylzinc, dimethylcadmium, and dimethyllead species via methylation of zinc (2+), cadmium (2+), and lead (2+) by a trans-dimethylcobalt complex
Witman MW and Weber JH
Inorganic Chemistry, 16(10), 2512-2515 (1977)
Tito Akindele et al.
Accounts of chemical research, 42(2), 345-355 (2008-12-31)
Developments in modern organic synthesis owe much to the field of radical chemistry. Mild reaction conditions, high selectivity, good functional group tolerance and high product yield are features that have made reactions involving radical species indispensable tools for synthetic chemists.
Copper-catalyzed asymmetric methylation of fluoroalkylated pyruvates with dimethylzinc.
Aikawa K, et al.
Beilstein Journal of Organic Chemistry, 14(1), 576-582 (2018)
Three-component catalytic asymmetric synthesis of aliphatic amines.
Porter JR, et al.
Journal of the American Chemical Society, 123(42), 10409-10410 (2001)
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