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Sigma-Aldrich

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
Beilstein:
3587195
MDL number:
MFCD00014854
UNSPSC Code:
12352103
PubChem Substance ID:
24866132
NACRES:
NA.22

form

liquid

concentration

1.0 M in heptane

bp

44-46 °C

density

0.724 g/mL at 25 °C

SMILES string

C[Zn]C

InChI

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

InChI key

AXAZMDOAUQTMOW-UHFFFAOYSA-N

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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.

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.

Signal Word

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 Code

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
A strategy for C-H activation of pyridines: direct C-2 selective alkenylation of pyridines by Nickel/Lewis Acid catalysis.
Nakao Y, et al.
Journal of the American Chemical Society, 130(8), 2448-2449 (2008)
Three-component catalytic asymmetric synthesis of aliphatic amines.
Porter JR, et al.
Journal of the American Chemical Society, 123(42), 10409-10410 (2001)
Dimethylzinc-mediated alkynylation of imines
Lorenzo Z et al.
The Journal of Organic Chemistry, 71, 1558-1562 (2006)
View All Related Papers

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