86386-67-6

Basic information

• Product Name: Formamide, N-[(4-chlorophenyl)methyl]-
• Synonyms: N-(4-chlorobenzyl)formamide;N-Formyl-p-chlorobenzylamin;4-chlorobenzylformamide;Formamide,N-[(4-chlorophenyl)methyl];4-Chlorbenzylformamid
• CAS NO: 86386-67-6
• Molecular Formula: C8H8ClNO
• Molecular Weight: 169.611
• Mol File: 86386-67-6.mol
• Article Data: 28

Chemical Properties

• CAS DataBase Reference: Formamide, N-[(4-chlorophenyl)methyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Formamide, N-[(4-chlorophenyl)methyl]-(86386-67-6)
• EPA Substance Registry System: Formamide, N-[(4-chlorophenyl)methyl]-(86386-67-6)

Safety Data

• Hazardous Substances Data: 86386-67-6(Hazardous Substances Data)

Upstream product

• 124-38-9 carbon dioxide 
• 104-86-9 4-chlorobenzylamine 
• 64-18-6 formic acid 
• 104-88-1 4-chlorobenzaldehyde 
• 77287-34-4 formamide 
• 68-12-2 N,N-dimethyl-formamide 
• 623-03-0 4-Cyanochlorobenzene 
• 67-56-1 methanol 
• 201230-82-2 carbon monoxide 
• 1188-33-6 N,N-dimethylformamide diethyl diacetal 
• 109-94-4 formic acid ethyl ester 

Downstream Products

• 1175033-55-2 N-[(4-chlorophenyl)methyl]thioformamide 
• 104936-75-6 N'-tert-Butyl-N-(4-chloro-benzyl)-N-methyl-formamidine 
• 3358-37-0 2-(4-chloro-phenyl)-1-methyl-piperidine 
• 104936-48-3 [1-(4-Chloro-phenyl)-pentyl]-methyl-amine 
• 104936-82-5 2-(4-chloro-phenyl)-1-methyl-pyrrolidine 
• 39546-47-9 p-chlorobenzylisocyanide 
• 104936-73-4 N-methyl-N-[(4-chlorophenyl)methyl]formamide 
• 3472-78-4 3-(4-Chlorphenyl)-1,1,3,3-tetrachlor-2-aza-propen-⁽¹⁾ 

Relevant articles and documents

Chromium-catalysed efficient: N -formylation of amines with a recyclable polyoxometalate-supported green catalyst

A simple and efficient protocol for the formylation of amines with formic acid, catalyzed by a polyoxometalate-based chromium catalyst, is described. Notably, this method shows excellent activity and chemoselectivity for the formylation of primary amines; diamines have also been successfully employed. Importantly, the chromium catalyst is potentially non-toxic, environmentally benign and safer than the widely used high valence chromium catalysts such as CrO3 and K2Cr2O7. The catalyst can be recycled several times with a negligible impact on activity. Finally, a plausible mechanism is provided based on the observation of intermediate and control experiments.

A NHC-silyliumylidene cation for catalytic N?formylation of amines using carbon dioxide

This study describes the use of a silicon(II) complex, namely, the NHC-silyliumylidene cation complex [(IMe)2SiH]I (1, IMe =:C{N(Me)C(Me)}2), to catalyze the chemoselective N-formylation of primary and secondary amines using CO2 and PhSiH3 under mild conditions to afford the corresponding formamides as a sole product (average reaction time: 4.5 h; primary amines, average yield: 95%, average TOF: 8 h?1; secondary amines, average yield: 98%, average TOF: 17 h?1). The activity of 1 and product yields outperform the currently available non-transition-metal catalysts used for this catalysis. Mechanistic studies show that the silicon(II) center in complex 1 catalyzes the C?N bond formation via a different pathway in comparison with non-transition-metal catalysts. It sequentially activates CO2, PhSiH3, and amines, which proceeds via a dihydrogen elimination mechanism, to form formamides, siloxanes, and dihydrogen gas.

One-step synthesis of N, N′-substituted 4-imidazolidinones by an isocyanide-based pseudo-five-multicomponent reaction

A pseudo-five-multicomponent reaction involving an isocyanide, a primary amine, two molecules of formaldehyde and water is reported, which gives N,N′-substituted 4-imidazolidinones when trifluoroethanol is used as the solvent. The reaction proceeds with good yields and with a wide variety of amines and isocyanides, providing an efficient new entry to these heterocycles. A preliminary study of the reaction mechanism suggests that trifluoroethanol, although acting as the solvent, is directly involved as a reagent in the reaction pathway.