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280909 Sigma-Aldrich

(Chloromethylene)dimethyliminium chloride

95%

Synonym: (Chlormethylene)dimethylammonium chloride, Arnold′s reagent, Dimethylchloroformiminium chloride, Vilsmeier reagent

  • CAS Number 3724-43-4

  • Linear Formula ClCH=N(CH3)2Cl

  • Molecular Weight 128.00

  •  Beilstein/REAXYS Number 3566322

  •  EC Number 425-970-6

  •  MDL number MFCD00011868

  •  PubChem Substance ID 24856957

  •  NACRES NA.22

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Properties

Related Categories C-C Bond Formation, Chemical Synthesis, Other Synthetic Reagents for C-C Bond Formation, Synthetic Reagents
Quality Level   200
assay   95%
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

Description

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

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Supplemental Hazard Statements 
EUH014
RIDADR 
UN 3261 8 / PGII
WGK Germany 
WGK 3

Documents

Certificate of Analysis (COA)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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