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162876

Sigma-Aldrich

Dichloromethylene-dimethyliminium chloride

technical grade

Synonym(s):

(Dichloromethylene)dimethylammonium chloride, Phosgeniminium chloride, Vilsmeier reagent

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About This Item

Linear Formula:
[Cl2C=N(CH3)2]+Cl-
CAS Number:
33842-02-3
Molecular Weight:
162.45
Beilstein:
4157987
EC Number:
251-695-4
MDL number:
MFCD00011870
UNSPSC Code:
12352100
PubChem Substance ID:
24850009
NACRES:
NA.22

grade

technical grade

mp

183-187 °C (dec.) (lit.)

storage temp.

2-8°C

SMILES string

[Cl-].C\[N+](C)=C(\Cl)Cl

InChI

1S/C3H6Cl2N.ClH/c1-6(2)3(4)5;/h1-2H3;1H/q+1;/p-1

InChI key

NRNFKRFWZQQDMD-UHFFFAOYSA-M

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General description

Dichloromethylene-dimethyliminium chloride (Vilsmeier reagent) reacts with o-acetaminophenols under Meth-Cohn conditions to yield 2-formylpyrido[2,1-b]benzoxazoles.

Application

Dichloromethylene-dimethyliminium chloride was used as reagent in the synthesis of selenourea and (R)-2-(2-chloroethyl)pyrrolidine-1-carboxylic acid ethyl ester. It was used for introducing amide chloride group into activated substrates.

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H314,H335

Hazard Classifications

Skin Corr. 1B - STOT SE 3

Target Organs

Respiratory system

Supplementary Hazards

EUH014

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
S56979V
MKBH7794V
S56979
02008HH
15822KN

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J. Prakt. Chem./Chem.-Ztg., 336, 561-561 (1994)
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The Journal of organic chemistry, 74(9), 3286-3292 (2009-04-01)
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