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417246

Sigma-Aldrich

二甲基锌 溶液

1.0 M in heptane

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别名:
Dimethylzinc
线性分子式:
(CH3)2Zn
CAS号:
544-97-8
分子量:
95.46
Beilstein:
3587195
MDL编号:
MFCD00014854
PubChem化学物质编号:
24866132
NACRES:
NA.22

形式

liquid

浓度

1.0 M in heptane

bp

44-46 °C

密度

0.724 g/mL at 25 °C

SMILES字符串

C[Zn]C

InChI

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

InChI key

AXAZMDOAUQTMOW-UHFFFAOYSA-N

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相关类别

一般描述

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.

应用

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.

警示用语：

Danger

危险分类

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

靶器官

Central nervous system

储存分类代码

4.2 - Pyrophoric and self-heating hazardous materials

WGK

WGK 3

闪点(°F)

30.2 °F - closed cup

闪点(°C)

-1 °C - closed cup

个人防护装备

Faceshields, Gloves, Goggles

法规信息

监管及禁止进口产品

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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)
Diethylzinc
Georges-Pierre and E
Synlett, 1937-1938 (2014)
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.
Dimethylzinc-mediated alkynylation of imines
Lorenzo Z et al.
The Journal of Organic Chemistry, 71, 1558-1562 (2006)
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