14315-16-3

Basic information

• Product Name: 3-AMINOBENZANILIDE
• Synonyms: 3-amino-benzanilid;3-aminobenzoicacidanilide;3-amino-n-phenyl-benzamid;M-AMINOBENZANILIDE;N-Phenyl-3-aminobenzamide;3-azanyl-N-phenyl-benzamide
• CAS NO: 14315-16-3
• Molecular Formula: C₁₃H₁₂N₂O
• Molecular Weight: 212.25
• EINECS: 238-257-8
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts
• Mol File: 14315-16-3.mol
• Article Data: 15

Chemical Properties

• Melting Point: 124～125℃
• Boiling Point: 323.9 °C at 760 mmHg
• Flash Point: 149.7 °C
• Appearance: /
• Density: 1.244 g/cm³
• Vapor Pressure: 0.000254mmHg at 25°C
• Refractive Index: 1.688
• CAS DataBase Reference: 3-AMINOBENZANILIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-AMINOBENZANILIDE(14315-16-3)
• EPA Substance Registry System: 3-AMINOBENZANILIDE(14315-16-3)

Safety Data

• Statements: 52/53
• HazardClass: IRRITANT
• Hazardous Substances Data: 14315-16-3(Hazardous Substances Data)

Usage

General Description

3-Aminobenzanilide, also known by its IUPAC name N-Phenyl-3-aminobenzoic acid anilide, is an organic chemical compound with the molecular formula C13H12N2O. It appears as a light yellow powder and primarily used in scientific research. It falls under the class of compounds known as benzamides, which are organic compounds containing a carboxamide group (CONH2) attached to a benzene ring. As with many chemicals, appropriate precautions should be taken while handling 3-aminobenzanilide as it may pose health and environmental risks.

InChI:InChI=1/C13H12N2O/c14-11-6-4-5-10(9-11)13(16)15-12-7-2-1-3-8-12/h1-9H,14H2,(H,15,16)

Upstream product

• 7664-93-9 sulfuric acid 
• 21563-72-4 3-Aminobenzoyl chloride 
• 62-53-3 aniline 
• 121-90-4 m-nitrobenzoic acid chloride 
• 15151-51-6 3-aminobenzoic acid hydrochloride 
• 121-92-6 3-nitrobenzoic acid 
• 111331-82-9 3-[(tert-butoxycarbonyl)amino]benzoic acid 
• 874337-73-2 C₁₈H₂₀N₂O₃ 
• 2243-73-4 5-nitrobenzanilide 
• 99-05-8 meta-aminobenzoic acid 

Downstream Products

• 90233-67-3 N-Phenyl-3-(pyrrolidine-1-sulfonylamino)-benzamide 
• 874337-76-5 diethyl ({[3-(anilinocarbonyl)phenyl]amino}methylene)malonate 
• 1400659-69-9 C₁₆H₁₅FN₂O₂ 
• 1395923-49-5 C₂₄H₂₂N₂O₂ 
• 1395923-14-4 C₂₈H₂₂N₂O₂ 
• 1395923-67-7 C₂₇H₂₀N₂O₃ 
• 1388657-36-0 3-(2-chloro-acetylamino)-N-phenylbenzamide 
• 1273179-12-6 3-[(diphenylthiophosphoryl)amino]-N-phenylbenzenecarbothioamide 
• 1273179-10-4 3-[(diphenylthiophosphoryl)amino]-N-phenylbenzamide 

Relevant articles and documents

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Fragmentation of Protonated N-(3-Aminophenyl)Benzamide and Its Derivatives in Gas Phase

An ion of m/z 110.06036 (ion formula [C6H8NO]+; error: 0.32 mDa) was observed in the collision induced dissociation tandem mass spectrometry experiments of protonated N-(3-aminophenyl)benzamide, which is a rearrangement product ion purportedly through nitrogen-oxygen (N–O) exchange. The N–O exchange rearrangement was confirmed by the MS/MS spectrum of protonated N-(3-aminophenyl)-O18-benzamide, where the rearranged ion, [C6H8NO18]+ of m/z 112 was available because of the presence of O18. Theoretical calculations using Density Functional Theory (DFT) at B3LYP/6-31?g(d) level suggest that an ion-neutral complex containing a water molecule and a nitrilium ion was formed via a transition state (TS-1), followed by the water molecule migrating to the anilide ring, eventually leading to the formation of the rearranged ion of m/z 110. The rearrangement can be generalized to other protonated amide compounds with electron-donating groups at the meta position, such as, –OH, –CH3, –OCH3, –NH(CH3)2, –NH-Ph, and –NHCOCH3, all of which show the corresponding rearranged ions in MS/MS spectra. However, the protonated amide compounds containing electron-withdrawing groups, including –Cl, –Br, –CN, –NO2, and –CF3, at the meta position did not display this type of rearrangement during dissociation. Additionally, effects of various acyl groups on the rearrangement were investigated. It was found that the rearrangement can be enhanced by substitution on the ring of the benzoyl with electron-withdrawing groups. [Figure not available: see fulltext.]

Synthesis and antiviral activity of substituted bisaryl amide compounds as novel influenza virus inhibitors

The influenza virus is a persistent cause of mortality and morbidity on an annual basis and thus presents itself as an important target for pharmaceutical investigation. In this work, substituted bisaryl amide compounds were found to be a new class of potential anti-influenza agents, and a series of substituted bisaryl amide compounds were synthesised and evaluated for their anti-influenza virus activities. The analysis of the results produced a preliminary structure-activity relationship study (SAR). Compounds 1a, 1g, 1h, 1j, 1l and 1n exhibited clear antiviral activities against the influenza A (A/Guangdong Luohu/219/2006, H1N1) virus with 50% inhibitory concentrations (IC50) for virus growth ranging from 12.5 to 59.0 μM. Specifically, compound 1j also possessed antiviral activity against both oseltamivir-resistant influenza (A/Jinnan/15/2009) virus and influenza B (B/Jifang/13/97) virus with IC 50 values of 9.2 μM and 21.4 μM, respectively. Compound 1j is thus worth further investigation as an anti-influenza virus candidate.