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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/REAXYS Number:
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

signalword

Danger

hcodes

H314,H335

Hazard Classifications

Skin Corr. 1B - STOT SE 3

target_organs

Respiratory system

supp_hazards

EUH014

Storage Class

8A - Combustible corrosive hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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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J. Prakt. Chem./Chem.-Ztg., 336, 561-561 (1994)
Ke-Lai Li et al.
The Journal of organic chemistry, 74(9), 3286-3292 (2009-04-01)
o-Acetaminophenols (2) reacted with Vilsmeier reagent under Meth-Cohn conditions to yield 2-formylpyrido[2,1-b]benzoxazoles (5) unexpectedly besides the known compounds 2-(benzoxazol-2'-yl)-3-dimethylaminoacroleins (4). Refluxing 4 in acetic anhydride gave 4-formylpyrido[2,1-b]benzoxazoles (6), an isomer of 5. Both 5a and 6a were structurally characterized by
A facile synthesis of N/C-terminal selenourea tethered glycosylated amino acids.
Sureshbabu VV, et al.
Indian J. Chem. B, 52(7), 895-900 (2013)
Asymmetric transformation of L-homoserine lactone to an optically active 2-substituted pyrrolidine for clemastine.
Kim SJ, et al.
Tetrahedron Asymmetry, 22(20), 1901-1905 (2011)
Ruhamah Yunis et al.
Physical chemistry chemical physics : PCCP, 21(23), 12288-12300 (2019-05-30)
The synthesis and characterisation of new solid-state electrolytes is a key step in advancing the development of safer and more reliable electrochemical energy storage technologies. Organic ionic plastic crystals (OIPCs) are an increasingly promising class of material for application in

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