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280909

Sigma-Aldrich

(Chloromethylene)dimethyliminium chloride

95%

Synonym(s):
Vilsmeier reagent, Dimethylchloroformiminium chloride, Arnold′s reagent, (Chlormethylene)dimethylammonium chloride
Linear Formula:
ClCH=N(CH3)2Cl
CAS Number:
Molecular Weight:
128.00
Beilstein:
3566322
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

95%

form

solid

reaction suitability

reaction type: C-C Bond Formation

impurities

<5% DMF

mp

132 °C (dec.) (lit.)

storage temp.

2-8°C

SMILES string

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

InChI

1S/C3H7ClN.ClH/c1-5(2)3-4;/h3H,1-2H3;1H/q+1;/p-1

InChI key

QQVDYSUDFZZPSU-UHFFFAOYSA-M

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Application

Reagent or Reactant for the synthesis of:
  • β-Lactams vis the Staudinger reaction
  • N-vinyl substituted indoles via cross coupling of NH-indoles with vinyl bromides
  • Multi ring-fused 2-pyridone-based fluorescent scaffold
  • ester prodrugs as anti-poxvirus agents
  • Trimethine cyanine dyes for sensing G-quadruplex formation
  • Phospha-isosteres via Hundsdiecker-Barton iododecacarboxylation
  • 2-Azetidinones via [2+2]-cycloaddition

Used for studying organic photosensitizers for application in dye-sensitized solar cells
Reagent used to prepare ß-lactams from ß-amino acids via carboxyl activation and cyclodehydration. Also used to convert α-aminonitriles into 4-chloroimidazoles.

Packaging

5, 25 g in glass bottle

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Repr. 1B - Skin Corr. 1A

Supplementary Hazards

Storage Class Code

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

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Certificate of Origin

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