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

Description

N-methylbenzanilide, with the molecular formula C14H13NO, is a white crystalline solid that serves as a versatile intermediate in the synthesis of pharmaceuticals, dyes, and other organic compounds. Its structure, featuring a benzene ring with a methyl and aniline group, endows it with both aromatic and amide properties, making it a stable and widely used compound in the chemical industry for diverse synthetic applications.

Uses

Used in Pharmaceutical Industry:
N-methylbenzanilide is used as a key intermediate for the production of various pharmaceuticals, leveraging its ability to participate in a wide range of chemical reactions to facilitate the synthesis of medicinal compounds.
Used in Dye Industry:
In the dye industry, N-methylbenzanilide is utilized as an intermediate for the synthesis of different types of dyes, capitalizing on its chemical properties to create a variety of colorants for various applications.
Used in Organic Synthesis:
N-methylbenzanilide is employed as a reagent in organic synthesis, where its versatility allows for the creation of a broad spectrum of organic molecules, contributing to the development of new chemical entities and materials.

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

• 93-98-1 N-phenyl benzoyl amide 
• 6780-39-8 E-[2-methoxy-1-phenyl-methylene]-phenylamine 
• 98-88-4 benzoyl chloride 
• 121-69-7 N,N-dimethyl-aniline 
• 100-61-8 N-methylaniline 
• 65-85-0 benzoic acid 
• 74-88-4 methyl iodide 
• 18106-71-3 dimethyl benzoylphosphonate 
• 74-96-4 ethyl bromide 
• 2628-58-2 N-methylthiobenzanilide 
• 88070-48-8 N-methylbenzamide 
• 83566-44-3 tetraphenylbismuth 4-methylbenzenesulfonate 
• 69859-25-2 3-chloro-N-methyl-N-phenylbenzothioamide 
• 33224-04-3 N-methyl-N-phenyl-2-nitrobenzenesulfenanilide 

Downstream Products

• 33672-82-1 N-(4-nitrophenyl)-N-methylbenzamide 
• 2628-58-2 N-methylthiobenzanilide 
• 56844-88-3 N'-benzyl-N-methyl-N-phenyl-benzamidine 
• 100-52-7 benzaldehyde 
• 4903-36-0 N-phenyl-benzimidoyl chloride 
• 479-45-8 tetryl 
• 93-89-0 benzoic acid ethyl ester 
• 72046-54-9 O,N-dimethyl-N-phenylbenzimidatonium trifluoromethanesulfonate 
• 530-44-9 4-(Dimethylamino)benzophenone 
• 74-87-3 methylene chloride 
• 614-30-2 N-methyl-N-phenyl-benzenemethanamine 
• 6941-23-7 1,2-bis(N-methyl-N-phenylamino)-1,2-diphenylethane 
• 100-61-8 N-methylaniline 
• 100-51-6 benzyl alcohol 

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.

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.

Pd-Catalyzed Double-Decarbonylative Aryl Sulfide Synthesis through Aryl Exchange between Amides and Thioesters

We report the palladium-catalyzed double-decarbonylative synthesis of aryl thioethers by an aryl exchange reaction between amides and thioesters. In this method, amides serve as aryl donors and thioesters are sulfide donors, enabling the synthesis of valuable aryl sulfides. The use of Pd/Xantphos without any additives has been identified as the catalytic system promoting the aryl exchange by C(O)-N/C(O)-S cleavages. The method is amenable to a wide variety of amides and sulfides.