(dichloromethylidene)dimethylazanium chloride

• ChemBase ID: 148068
• Molecular Formular: C3H6Cl3N
• Molecular Mass: 162.44544
• Monoisotopic Mass: 160.95658224
• SMILES: C[N+](=C(Cl)Cl)C.[Cl-]
• Canonical SMILES: ClC(=[N+](C)C)Cl.[Cl-]
• InChI: InChI=1S/C3H6Cl2N.ClH/c1-6(2)3(4)5;/h1-2H3;1H/q+1;/p-1
• InChIKey: NRNFKRFWZQQDMD-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: (dichloromethylidene)dimethylazanium chloride
• IUPAC Traditional name: (dichloromethylidene)dimethylazanium chloride
• Synonyms: Phosgeniminium chloride; (Dichloromethylene)dimethylammonium chloride; Vilsmeier reagent; Dichloromethylene-dimethyliminium chloride; N,N-Dimethylphosgeniminium chloride; "Phosgeniminium chloride"; (Dichloromethylene)dimethylammonium chloride; (二氯亚甲基)二甲基氯化铵; Vilsmeier 试剂; 二氯亚甲基二甲基氯化铵; (二氯亚甲基)二甲基氯化铵

Database IDs

• CAS Number: 33842-02-3
• EC Number: 251-695-4
• MDL Number: MFCD00011870
• Beilstein Number: 4157987
• PubChem SID: 24850009; 162242246
• PubChem CID: 2723945

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): -1.963418
• LogD (pH = 7.4): -1.963418
• Log P: -1.963418
• Molar Refractivity: 40.2806 cm^3
• Polarizability: 11.098925 Å^3
• Polar Surface Area: 3.01 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 183-187 °C (dec.)(lit.); ca 185°C dec.

Safety Information

• Storage Warning: Moisture Sensitive
• European Hazard Symbols: Corrosive (C)
• UN Number: 3261; UN3261
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 3; II
• Risk Statements: 14-34; 14-34-37
• Safety Statements: 26-36/37/39-45
• TSCA Listed: 否
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H314-H318; H314-H335
• GHS Precautionary statements: P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A; P261-P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 3261 8/PG 3
• Supplemental Hazard Statements: Reacts violently with water.
• Storage Temperature: 2-8°C

Product Information

• Purity: 95%
• Grade: technical grade
• Linear Formula: [Cl2C=N(CH3)2]+Cl-

DETAILS

Sigma Aldrich - 162876

Application
Introduces amide chloride group into activated substrates.1
Packaging
5, 25 g in glass bottle

REFERENCES

• Reaction with a phenol yields, after hydrolysis, the diaryl carbonate: Angew. Chem. Int. Ed., 10, 573 (1971). For reactions with active methylene compounds, see: Angew. Chem. Int. Ed., 10, 574, 575 (1971). 2-Hydroxy acetophenones lead to 2-dimethylamino chromones: J. Org. Chem., 57, 6502 (1992); 61, 3218 (1996):
  
• Dehydrates aldoximes and aldehyde phenylhydrazones to nitriles: Synthesis, 563 (1974), 201 (1985), respectively. N, N-dialkylureas are dehydrated to carbodiimides: Tetrahedron Lett., 37, 7047 (1996).
• Converts THP protected alcohols directly to alkyl chlorides in good yield: Tetrahedron Lett., 38, 3517 (1997).
• For review of reactions, including use as Mannich or Vilsmeier intermediates, see: Angew. Chem. Int. Ed., 12, 806 (1973).
• See also (Chloromethylene)dimethylammonium chloride, B24172.
• Effects cyanation of electron-rich aromatics and heterocycles: Tetrahedron Lett., 27, 1939 (1986).