58569-87-2

Basic information

• Product Name: N-(1-chloroethylidene)-N-methylmethanaminium chloride
• Synonyms: methanaminium, N-(1-chloroethylidene)-N-methyl-, chloride (1:1); N-(1-Chloroethylidene)-N-methylmethanaminium chloride
• CAS NO: 58569-87-2
• Molecular Formula: C₄H₉ClN*Cl
• Molecular Weight: 142.027
• Mol File: 58569-87-2.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: N-(1-chloroethylidene)-N-methylmethanaminium chloride(CAS DataBase Reference)
• NIST Chemistry Reference: N-(1-chloroethylidene)-N-methylmethanaminium chloride(58569-87-2)
• EPA Substance Registry System: N-(1-chloroethylidene)-N-methylmethanaminium chloride(58569-87-2)

Safety Data

• Hazardous Substances Data: 58569-87-2(Hazardous Substances Data)

Upstream product

• 67-66-3 chloroform 
• 127-19-5 N,N-dimethyl acetamide 
• 18871-66-4 N,N-dimethylacetamide dimethyl acetal 
• 75-44-5 phosgene 

Downstream Products

• 932-16-1 N-methyl-2-acetylpyrrole 
• 932-62-7 3-acetyl-1-methyl-1H-pyrrole 
• 1072-83-9 2-Acetylpyrrole 
• 1193-79-9 2-acetyl-5-methylfuran 
• 123-86-4 acetic acid butyl ester 
• 2623-23-6 L-menthyl acetate 
• 58114-25-3 N,N-dimethylaminoethane hydrochloride 
• 5525-85-9 N-Cyclohexylbrenztraubensaeure-amid 

Relevant articles and documents

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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.

A One-Pot Synthesis of Highly Functionalized Purines

Highly substituted purines were synthesized in good to high yields through a one-pot straightforward metal-free scalable method, using the Traube synthesis adapted to Vilsmeier-type reagents. From 5-amino-4-chloropyrimidines, new 9-aryl-substituted chloropurines and intermediates for peptide nucleic acid synthesis were prepared. Variant procedures allowing a rapid synthesis of ribonucleosides and 7-benzylpurine from 5-amidino-6-aminopyrimidines are also reported to illustrate the high potential of this versatile toolbox. This route appears to be particularly interesting in the field of nucleic acids for a direct and rapid access to various new 8-alkylpurine nucleosides.

Syntheses of 4-substituted 2-(trichloromethyl)quinazolines under mild conditions by benzyne [4+2] cycloaddition

An experimentally simple and convenient synthesis of 4-susbstituted 2-(trichloromethyl)quinazolines by cycloaddition of benzyne with 2-(trichloromethyl)-1,3-diazabutadienes was developed. The 2-(trichloromethyl)-1,3-diazabutadienes (R1 = H and Me) were prepared from trichloroacetamidine and the appropriate N,N-dimethylamide dimethyl acetal or from trichloroacetamidine and a Vilsmeier-Haack reagent containing an aryl group.