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364401

Sigma-Aldrich

Dimethylzinc solution

2.0 M in toluene

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:
24862428
NACRES:
NA.22

Quality Level

100

concentration

2.0 M in toluene

density

0.931 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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Application

Dimethylzinc 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 enantioselective synthesis of alkyl and aralkyl secondary amines via one-pot three-component coupling reaction in the presence of zirconium tetraisopropoxide.
  • A methylating reagent for the methylation of fluoroalkylated pyruvates in the presence of a copper/chiral diphosphine catalyst.
  • An activator for radical trifluoromethylation of silyl enol ethers leading to α-trifluoromethyl ketones.

Signal Word

Danger

Hazard Classifications

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

Target Organs

Central nervous system

Storage Class Code

4.2 - Pyrophoric and self-heating hazardous materials

WGK

WGK 3

Flash Point(F)

1.4 °F - closed cup

Flash Point(C)

-17 °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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Koichi Mikami et al.
Organic letters, 8(21), 4671-4673 (2006-10-06)
[reaction: see text] The radical trifluoromethylation of ketone silyl enol ethers gave alpha-CF(3) ketones in good yields with wide scope of the ketonic substrates including acyclic ketones and cyclopentanone. The use of dialkylzinc to activate the silyl enol ethers is
Radical trifluoromethylation of ketone silyl enol ethers by activation with dialkylzinc.
Mikami K, et al.
Organic Letters, 8(21), 4671-4673 (2006)
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)
Copper-catalyzed asymmetric methylation of fluoroalkylated pyruvates with dimethylzinc.
Aikawa K, et al.
Beilstein Journal of Organic Chemistry, 14(1), 576-582 (2018)

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