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Merck

417246

Dimethylzinc solution

1.0 M in heptane

Synonym(s):

Dimethylzinc

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About This Item

Linear Formula:
(CH3)2Zn
CAS Number:
544-97-8
Molecular Weight:
95.46
UNSPSC Code:
12352103
NACRES:
NA.22
PubChem Substance ID:
24866132
MDL number:
MFCD00014854
Beilstein/REAXYS Number:
3587195

Key Documents

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Product Name

Dimethylzinc solution, 1.0 M in heptane

InChI

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

SMILES string

C[Zn]C

InChI key

AXAZMDOAUQTMOW-UHFFFAOYSA-N

form

liquid

concentration

1.0 M in heptane

bp

44-46 °C

density

0.724 g/mL at 25 °C

Quality Level

100

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Application

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.

General description

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.

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Danger

Hazard Classifications

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

target_organs

Central nervous system

Storage Class

4.2 - Pyrophoric and self-heating hazardous materials

wgk

WGK 3

flash_point_f

30.2 °F - closed cup

flash_point_c

-1 °C - closed cup

ppe

Faceshields, Gloves, Goggles

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Certificates of Analysis (COA)

Lot/Batch Number
SHBN5111
SHBL2186
SHBJ4691
SHBH1126V
SHBF9286V

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