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417297

Sigma-Aldrich

Methylzinc chloride solution

2.0 M in THF

Synonym(s):

Chloromethylzinc

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About This Item

Linear Formula:
CH3ZnCl
CAS Number:
5158-46-3
Molecular Weight:
115.88
Beilstein:
969141
MDL number:
MFCD00192334
UNSPSC Code:
12352103
PubChem Substance ID:
24866136
NACRES:
NA.22

form

liquid

concentration

2.0 M in THF

bp

67 °C

density

1.033 g/mL at 25 °C

SMILES string

C[Zn]Cl

InChI

1S/CH3.ClH.Zn/h1H3;1H;/q;;+1/p-1

InChI key

ASUSLKVOTPUROZ-UHFFFAOYSA-M

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Application

Methylzinc chloride can be used in:
  • Ni-catalyzed one-pot Negishi coupling with amino-heteroaryl chlorides.
  • Cross-coupling with aryl fluorides in the presence of a nickel catalyst.

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Oral - Carc. 2 - Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1B - STOT SE 3

Target Organs

Respiratory system

Supplementary Hazards

EUH019

Storage Class Code

3 - Flammable liquids

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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A convenient one-pot Negishi coupling of amino-heteroaryl chlorides and alkyl bromides
Walters IAS
Tetrahedron Letters, 47(3), 341-344 (2006)
Nickel-catalyzed cross-coupling of aryl fluorides and organozinc reagents
Zhu F and Wang Z
The Journal of Organic Chemistry, 79(10), 4285-4292 (2014)

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