280909

(Chloromethylene)dimethyliminium chloride

95%

• Synonym(s): (Chlormethylene)dimethylammonium chloride, Arnold′s reagent, Dimethylchloroformiminium chloride, Vilsmeier reagent
• Linear Formula: ClCH=N(CH₃)₂Cl
• CAS Number: 3724-43-4
• Molecular Weight: 128.00
• UNSPSC Code: 12352101
• NACRES: NA.22
• PubChem Substance ID: 24856957
• EC Number: 425-970-6
• Beilstein/REAXYS Number: 3566322
• MDL number: MFCD00011868
• Assay: 95%
• Form: solid

Properties

• Quality Level: 200
• assay: 95%
• form: solid
• reaction suitability: reaction type: C-C Bond Formation
• impurities: <5% DMF
• mp: 132 °C (dec.) (lit.)
• functional group: amine, chloro
• 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 β-lactams from β-amino acids via carboxyl activation and cyclodehydration. Also used to convert α-aminonitriles into 4-chloroimidazoles.

Safety Information

• pictograms: GHS08,GHS05,GHS07
• signalword: Danger
• hcodes: H302,H314,H360D
• pcodes: P260 - P280 - P301 + P312 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338
• Hazard Classifications: Acute Tox. 4 Oral - Eye Dam. 1 - Repr. 1B - Skin Corr. 1A
• supp_hazards: EUH014
• Storage Class: 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
• ppe: Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges