1934-92-5

Basic information

• Product Name: N-methylbenzanilide
• Synonyms: N-methylbenzanilide;N-Benzoyl-N-methylaniline;N-Methyl-N-phenylbenzamide;N-Phenyl-N-methylbenzamide
• CAS NO: 1934-92-5
• Molecular Formula: C₁₄H₁₃NO
• Molecular Weight: 211.25912
• EINECS: 217-704-0
• Mol File: 1934-92-5.mol
• Article Data: 144

Chemical Properties

• Melting Point: 57.5-59 °C
• Boiling Point: 341.3°Cat760mmHg
• Flash Point: 154.4°C
• Appearance: /
• Density: 1.13g/cm³
• Vapor Pressure: 8.12E-05mmHg at 25°C
• Refractive Index: 1.618
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 0.41±0.50(Predicted)
• CAS DataBase Reference: N-methylbenzanilide(CAS DataBase Reference)
• NIST Chemistry Reference: N-methylbenzanilide(1934-92-5)
• EPA Substance Registry System: N-methylbenzanilide(1934-92-5)

Safety Data

• Hazardous Substances Data: 1934-92-5(Hazardous Substances Data)

Usage

General Description

N-methylbenzanilide is a chemical compound with the molecular formula C14H13NO. It is a white crystalline solid that is commonly used as an intermediate in the production of pharmaceuticals, dyes, and other organic compounds. N-methylbenzanilide is also utilized as a reagent for the synthesis of various organic molecules, due to its ability to participate in a wide range of reactions. Its structure includes a benzene ring with a methyl and aniline group attached, giving it both aromatic and amide properties. Due to its versatility and stability, N-methylbenzanilide is widely employed in the chemical industry for various synthetic applications.

InChI:InChI=1/C14H13NO/c1-15(13-10-6-3-7-11-13)14(16)12-8-4-2-5-9-12/h2-11H,1H3

Upstream product

• 98-88-4 benzoyl chloride 
• 121-69-7 N,N-dimethyl-aniline 
• 100-61-8 N-methylaniline 
• 65-85-0 benzoic acid 
• 93-98-1 N-phenyl benzoyl amide 
• 74-88-4 methyl iodide 
• 18106-71-3 dimethyl benzoylphosphonate 
• 33224-04-3 N-methyl-N-phenyl-2-nitrobenzenesulfenanilide 
• 591-51-5 phenyllithium 
• 1117-97-1 N,0-dimethylhydroxylamine 
• 77-78-1 dimethyl sulfate 
• 24197-72-6 S-(2-nitrophenyl)benzenecarbothiolate 
• 4931-66-2 methyl 5-oxopyrrolidine-2-carboxylate 
• 591-50-4 iodobenzene 

Downstream Products

• 93-89-0 benzoic acid ethyl ester 
• 72046-54-9 O,N-dimethyl-N-phenylbenzimidatonium trifluoromethanesulfonate 
• 479-45-8 tetryl 
• 59073-67-5 N-methyl-N-(α-methylsulfanyl-benzyliden)-anilinium; iodide 
• 100-51-6 benzyl alcohol 
• 100-61-8 N-methylaniline 
• 1618672-97-1 dimethyl 2-[(N-methyl-N-phenylamino)(phenyl)methylene]malonate 
• 119-61-9 benzophenone 
• 5123-13-7 5,5-dimethyl-2-phenyl-1,3,2-dioxaborinane 
• 1439356-84-9 methyl 1-methyl-4-oxo-2-phenyl-1,4-dihydroquinoline-3-carboxylate 
• 15190-67-7 α-(N-methylanilino)-α-phenylacetonitrile 
• 54343-55-4 3-Benzoyl-1-methyl-2-pyrrolidinone 
• 50361-97-2 3-benzoyl-1-methylpiperidin-2-one 
• 18871-71-1 N,N-dimethyl 3-oxo-3-phenyl-propanamide 

Relevant articles and documents

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Simple and convenient synthesis of tertiary benzanilides using dichlorotriphenylphosphorane

Various tertiary benzanilide derivatives were effectively synthesized from substituted benzoic acid and N-monoalkylated aniline using dichlorotriphenylphosphorane in chloroform. Yields were generally high, even when an electron-withdrawing group substituted the aromatic ring of aniline, or when an electron-donating group substituted the aromatic ring of benzoic acid. Allyl, Boc, MPM and the Z group were unaffected under these conditions.

PCl3-mediated transesterification and aminolysis of tert-butyl esters via acid chloride formation

A PCl3-mediated conversion of tert-butyl esters into esters and amides in one-pot under air is developed. This novel protocol is highlighted by the synthesis of skeletons of bioactive molecules and gram-scale reactions. Mechanistic studies revealed that this transformation involves the formation of an acid chloride in situ, which is followed by reactions with alcohols or amines to afford the desired products.

Direct Amidation of Esters by Ball Milling**

The direct mechanochemical amidation of esters by ball milling is described. The operationally simple procedure requires an ester, an amine, and substoichiometric KOtBu and was used to prepare a large and diverse library of 78 amide structures with modest to excellent efficiency. Heteroaromatic and heterocyclic components are specifically shown to be amenable to this mechanochemical protocol. This direct synthesis platform has been applied to the synthesis of active pharmaceutical ingredients (APIs) and agrochemicals as well as the gram-scale synthesis of an active pharmaceutical, all in the absence of a reaction solvent.