23896-88-0

Basic information

• Product Name: N-(2-METHOXY-PHENYL)-FORMAMIDE
• Synonyms: N-(2-METHOXY-PHENYL)-FORMAMIDE;(2-Methoxyanilino)formaldehyde;NSC-53664;ORTHO-FORMANISIDIDE
• CAS NO: 23896-88-0
• Molecular Formula: C₈H₉NO₂
• Molecular Weight: 151.16
• Mol File: 23896-88-0.mol
• Article Data: 52

Chemical Properties

• Melting Point: 84 °C
• Boiling Point: 328.7°Cat760mmHg
• Flash Point: 152.6°C
• Appearance: /
• Density: 1.16g/cm³
• Vapor Pressure: 0.000186mmHg at 25°C
• Refractive Index: 1.57
• PKA: 14.37±0.70(Predicted)
• CAS DataBase Reference: N-(2-METHOXY-PHENYL)-FORMAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2-METHOXY-PHENYL)-FORMAMIDE(23896-88-0)
• EPA Substance Registry System: N-(2-METHOXY-PHENYL)-FORMAMIDE(23896-88-0)

Safety Data

• Hazardous Substances Data: 23896-88-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C8H9NO2/c1-11-8-5-3-2-4-7(8)9-6-10/h2-6H,1H3,(H,9,10)

Upstream product

• 90-04-0 2-methoxy-phenylamine 
• 149-73-5 trimethyl orthoformate 
• 123-91-1 1,4-dioxane 
• 10541-78-3 2-methoxy-N-methylaniline 
• 51673-84-8 dimethoxyacetaldehyde 
• 667-27-6 Ethyl bromodifluoroacetate 
• 91-23-6 2-Nitroanisole 
• 16712-16-6 ammonium formate 
• 31791-97-6 2-methoxybenzohydroxamic acid 
• 77287-34-4 formamide 
• 21615-34-9 2-Methoxybenzoyl chloride 
• 1988-22-3 4-chlorophenyl formate 
• 141-53-7 sodium formate 
• 68-12-2 N,N-dimethyl-formamide 

Downstream Products

• 10541-78-3 2-methoxy-N-methylaniline 
• 15258-52-3 N-allyl-N-methyl-o-anisidine 
• 151657-66-8 N-benzyl-N-methyl-o-anisidine 
• 90-04-0 2-methoxy-phenylamine 
• 28354-25-8 2-((2-methoxyphenyl)amino) acetonitrile 
• 71862-04-9 N-(2-methoxy-4-nitrophenyl)formamide 
• 14223-46-2 o-Methoxy-phenylisoselenocyanat, o-Methoxy-phenylselenosenfoel 
• 952959-44-3 1-(2-methoxyphenyl)-1H-imidazole-4-carboxylic acid 
• 6609-56-9 2-methoxy-benzonitrile 

Relevant articles and documents

Copper-Catalyzed Cascade N-Dealkylation/N-Methyl Oxidation of Aromatic Amines by Using TEMPO and Oxygen as Oxidants

A novel tandem N-dealkylation and N-methyl aerobic oxidation of tertiary aromatic amines to N-arylformamides using copper and TEMPO has been developed. This methodology suggested an alternative synthetic route from N-methylarylamines to N-arylformamides.

HCl-mediated transamidation of unactivated formamides using aromatic amines in aqueous media

We report transamidation protocol to synthesize a range of secondary and tertiary amides from weakly nucleophilic aromatic and hetero-aryl amines with low reactive formamide derivatives, utilizing hydrochloric acid as catalyst. This current acid mediated strategy is beneficial because it eliminates the need for a metal catalyst, promoter or additives in the reaction, simplifies isolation and purification. Notably, this approach conventionally used to synthesize molecules on gram scales with excellent yields and a high tolerance for functional groups.

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.