3724-43-4

Basic information

• Product Name: (Chloromethylene)dimethyliminium chloride
• Synonyms: (CHLOROMETHYLENE)DIMETHYLAMMONIUM CHLORIDE;CHLOROMETHYLENEDIMETHYLIMINIUM CHLORIDE;N-CHLOROMETHYLEN-N,N-DIMETHYLAMMONIUM CHLORIDE;VILSMEIER REAGENT;(Chloromethylene)dimethylammoniumchlorlde;n-(chloromethylene)-n-methyl-methanaminiuchloride;Vilsmeier;N-Chloromethylene-N,N-Dimethyl Ammonium Chloride
• CAS NO: 3724-43-4
• Molecular Formula: C₃H₇ClN*Cl
• Molecular Weight: 128
• EINECS: 425-970-6
• Mol File: 3724-43-4.mol
• Article Data: 21

Chemical Properties

• Melting Point: 132 °C (dec.)(lit.)
• Boiling Point: 204.27°C (rough estimate)
• Flash Point: °C
• Appearance: Pale brown to yellow-brown/Crystalline Powder
• Density: 1.3578 (rough estimate)
• Refractive Index: 1.4525 (estimate)
• Storage Temp.: 2-8°C
• Water Solubility: reacts
• Sensitive: Moisture Sensitive
• BRN: 3566322
• CAS DataBase Reference: (Chloromethylene)dimethyliminium chloride(CAS DataBase Reference)
• NIST Chemistry Reference: (Chloromethylene)dimethyliminium chloride(3724-43-4)
• EPA Substance Registry System: (Chloromethylene)dimethyliminium chloride(3724-43-4)

Safety Data

• Hazard Codes: T
• Statements: 61-20/21/22-34-22-14-35
• Safety Statements: 53-26-36/37/39-45
• RIDADR: UN 3261
• WGK Germany: 1
• F: 8-10
• TSCA: Yes
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 3724-43-4(Hazardous Substances Data)

Usage

Chemical Properties

Pale brown to yellowish-brown crystalline powder

Uses

Different sources of media describe the Uses of 3724-43-4 differently. You can refer to the following data:
1. (Chloromethylene)dimethylammonium chloride is used in the synthesis of beta-lactams, n-vinyl substituted indoles and fused 2-pyridone rings and 2-azetidinones. It is used as a formylating agent and used in the preparation of anti-poxvirus agents. It is used in Staudinger reaction and Hundsdiecker-barton iododecarboxylation reaction. It is widely used for studying organic photosensitizers, which finds application in dye-sensitized solar cells.
2. Reagent or Reactant for the synthesis of: β-Lactams vis the Staudinger reactionN-vinyl substituted indoles via cross coupling of NH-indoles with vinyl bromidesMulti ring-fused 2-pyridone-based fluorescent scaffoldester prodrugs as anti-poxvirus agentsTrimethine cyanine dyes for sensing G-quadruplex formationPhospha-isosteres via Hundsdiecker-Barton iododecacarboxylation2-Azetidinones via [2+2]-cycloadditionUsed for studying organic photosensitizers for application in dye-sensitized solar cells

InChI:InChI=1/C3H7ClN/c1-5(2)3-4/h3H,1-2H3/q+1

Upstream product

• 75-44-5 phosgene 
• 68-12-2 N,N-dimethyl-formamide 
• 79-37-8 oxalyl dichloride 
• 18964-31-3 2,3-dichloro-5-dichloromethylene-2-cyclopentene-1,4-dione 
• 88-95-9 Phthaloyl dichloride 
• 67-66-3 chloroform 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 32315-10-9 bis(trichloromethyl) carbonate 

Downstream Products

• 100-10-7 4-dimethylamino-benzaldehyde 
• 4351-55-7 cholesteryl formate 
• 98-09-9 benzenesulfonyl chloride 
• 73759-73-6 Chlormalondialdehyd-anil 
• 6006-65-1 N,N-dimethylformamide dipropyl acetal 
• 1188-33-6 N,N-dimethylformamide diethyl diacetal 
• 7089-20-5 [3-chloro-3-(4-chloro-phenyl)-allylidene]-dimethyl-ammonium; perchlorate 
• 4291-13-8 2-(4-nitrophenyl)-1,3,4-oxadiazole 
• 91395-88-9 β-Chlor-4-dimethylamino-α-formyl-zimtaldehyd 
• 91395-82-3 β-Chlor-4-dimethylamino-3-formyl-zimtaldehyd 
• 1192-58-1 N-methylpyrrole aldehyde 
• 36929-60-9 3-formyl-1-methylpyrrole 
• 51076-46-1 2-(4-pyridyl)-propan-1,3-dione 
• 80645-64-3 1-(N,N-Dimethylamino)-3-(N,N-dimethyl)-2-(pyrid-4-yl)-prop-1-en-chlorid-hydrochlorid 

Relevant articles and documents

Photo-on-Demand Synthesis of Vilsmeier Reagents with Chloroform and Their Applications to One-Pot Organic Syntheses

The Vilsmeier reagent (VR), first reported a century ago, is a versatile reagent in a variety of organic reactions. It is used extensively in formylation reactions. However, the synthesis of VR generally requires highly toxic and corrosive reagents such as POCl3, SOCl2, or COCl2. In this study, we found that VR is readily obtained from a CHCl3 solution containing N,N-dimethylformamide or N,N-dimethylacetamide upon photo-irradiation under O2 bubbling. The corresponding Vilsmeier reagents were obtained in high yields with the generation of gaseous HCl and CO2 as byproducts to allow their isolations as crystalline solid products amenable to analysis by X-ray crystallography. With the advantage of using CHCl3, which bifunctionally serves as a reactant and a solvent, this photo-on-demand VR synthesis is available for one-pot syntheses of aldehydes, acid chlorides, formates, ketones, esters, and amides.

PROCESS FOR PREPARING SOLID (CHLORINE METHYLENE) DIMETHYL AMMONIUM CHLORIDE

Solid (chloro methylene) dimethyl ammonium chloride of in manufacturing method, said method, and phthalic anhydride raw material is first acyl with Neel thio chloride and method for chlorinating side is performed on the stacking section for stacking o-reel chloride, again chloride reel-o N, reacts with N-dimethylformamide (chloro methylene) dimethyl ammonium chloride and, and phthalic anhydride is obtained, N of increased amount of generated, and phthalic anhydride, dissolving the-dimethylformamide N, solid-liquid through separation of solid (chloro methylene) dimethyl ammonium chloride to obtain. the method number 1-step reaction through the interrupt input is an input from the data input sulfur dioxide, high vacuum under conditions protruded from sulfur dioxide and does not require the removal of, , moderating reaction conditions, to implemented very easily in.

New preparation method for Vilsmeier reagent and related imidoyl chlorides

An environmentally benign and inexpensive preparation method is described of some imidoyl chlorides, including the Vilsmeier reagent (VR), by using phthaloyl dichloride. Synthetic applications were demonstrated using the isolated VR or VR prepared in situ for the transformation of acids to acid chlorides, alcohols to chlorides, and the formylation of dimethylaminobenzene.