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

Description

(Chloromethylene)dimethyliminium chloride, also known as (Chloromethylene)dimethylammonium chloride, is a pale brown to yellowish-brown crystalline powder. It is a versatile reagent or reactant used in various chemical reactions and synthesis processes due to its unique chemical properties.

Uses

Used in Pharmaceutical Synthesis:
(Chloromethylene)dimethyliminium chloride is used as a formylating agent for the synthesis of beta-lactams, which are essential components in the development of antibiotics. It is also used in the preparation of anti-poxvirus agents, contributing to the development of treatments for viral infections.
Used in Organic Chemistry:
In the field of organic chemistry, (Chloromethylene)dimethyliminium chloride serves as a reagent or reactant for the synthesis of various compounds, including:
N-vinyl substituted indoles via cross-coupling of NH-indoles with vinyl bromides
Multi-ring-fused 2-pyridone-based fluorescent scaffolds
Ester prodrugs as anti-poxvirus agents
Trimethine cyanine dyes for sensing G-quadruplex formation
Phospha-isosteres via Hundsdiecker-Barton iododecarboxylation
2-Azetidinones via [2+2]-cycloaddition
Used in Material Science:
(Chloromethylene)dimethyliminium chloride is widely used for studying organic photosensitizers, which find application in dye-sensitized solar cells. This contributes to the development of more efficient and sustainable energy sources.

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 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 88-95-9 Phthaloyl dichloride 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 67-66-3 chloroform 

Downstream Products

• 100-10-7 4-dimethylamino-benzaldehyde 
• 4351-55-7 cholesteryl formate 
• 98-09-9 benzenesulfonyl chloride 
• 14758-19-1 (β,β'-dichloro-isopropyl)-dimethyl-amine 
• 73759-73-6 Chlormalondialdehyd-anil 
• 6006-65-1 N,N-dimethylformamide dipropyl acetal 
• 5239-65-6 N,N'-Dicyclohexyl-α--malonamid 
• 23587-42-0 Tetramethyl <(Dimethylamino)methylene>bisphosphonate 
• 1188-33-6 N,N-dimethylformamide diethyl diacetal 
• 100378-98-1 1,2,3,4-tetrakis-formyloxy-butane 
• 905-96-4 3,3'-diethyloxacarbocyanine iodide 
• 7089-20-5 [3-chloro-3-(4-chloro-phenyl)-allylidene]-dimethyl-ammonium; perchlorate 
• 4291-13-8 2-(4-nitrophenyl)-1,3,4-oxadiazole 
• 18855-52-2 tetraethyl dimethylaminomethylenediphosphonate 

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.