93-98-1

Basic information

• Product Name: BENZANILIDE
• Synonyms: N-PHENYLBENZAMIDE;N-BENZOYLANILINE;BENZANILIDE;Benzamide, N-phenyl-;Benzamide,N-phenyl-;Benzanilid;Benzoic acid anilide;Benzoylanilide
• CAS NO: 93-98-1
• Molecular Formula: C₁₃H₁₁NO
• Molecular Weight: 197.23
• EINECS: 202-292-7
• Product Categories: Pharmaceutical Intermediates
• Mol File: 93-98-1.mol
• Article Data: 1061

Chemical Properties

• Melting Point: 161-163 °C(lit.)
• Boiling Point: 117 °C10 mm Hg(lit.)
• Flash Point: 117°C/10mm
• Appearance: Grayish to yellow-green/Powder
• Density: 1,315 g/cm3
• Vapor Pressure: 0.0261mmHg at 25°C
• Refractive Index: 1.6050 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: H2O: insoluble
• PKA: 13.52±0.70(Predicted)
• Water Solubility: Insoluble
• Merck: 14,1061
• BRN: 1102980
• CAS DataBase Reference: BENZANILIDE(CAS DataBase Reference)
• NIST Chemistry Reference: BENZANILIDE(93-98-1)
• EPA Substance Registry System: BENZANILIDE(93-98-1)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 22-24/25-36-26
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 93-98-1(Hazardous Substances Data)

Usage

Chemical Properties

greyish to yellow-green powder

Uses

Different sources of media describe the Uses of 93-98-1 differently. You can refer to the following data:
1. manufacture of dyes and perfumes.
2. Benzanilide is used to make dyes, active pharmaceutical ingredients and perfumes. It is also used to study the influence of beta-cyclodextrin on photorearrangement of acetanilide, benzanilide and ethyl phenyl carbonate. Further, it is used as an amide model compound to study the reaction between the amide and epoxy. In addition to this, it reacts with aryltriflates in the presence of palladium-based catalyst system to get N-(2,6-diarylbenzoyl)anilines.

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 24, p. 187, 1987 DOI: 10.1002/jhet.5570240135The Journal of Organic Chemistry, 20, p. 1482, 1955 DOI: 10.1021/jo01128a004Tetrahedron Letters, 31, p. 1063, 1990 DOI: 10.1016/S0040-4039(00)94431-9

General Description

Benzanilide undergoes diarylation with aryl triflates or bromides in the presence of a palladium-based catalyst system to form corresponding N-(2,6-diarylbenzoyl)anilines. It is used in manufacture of dyes and perfumes.

Purification Methods

Crystallise benzanilide from pet ether (b 70-90o) using a Soxhlet extractor, and dry it overnight at 120o. Also crystallise it from EtOH. [Beilstein 12 IV 417.]

InChI:InChI=1/C13H11NO/c15-13(11-7-3-1-4-8-11)14-12-9-5-2-6-10-12/h1-10H,(H,14,15)

Upstream product

• 110-86-1 pyridine 
• 574-66-3 Benzophenone oxime 
• 98-09-9 benzenesulfonyl chloride 
• 79-37-8 oxalyl dichloride 
• 60-29-7 diethyl ether 
• 940-38-5 phenylcarbamoyl azide 
• 64-17-5 ethanol 
• 23796-78-3 N,N'-dibenzoyl-N,N'-diphenyl-thiourea 
• 141-52-6 sodium ethanolate 
• 43199-43-5 benzoic acid-(phenyl-dithiocarbamic acid )-anhydride 
• 4971-80-6 ethyl N-benzoylcarbamate 
• 859202-68-9 5-anilino-3-methyl-5-phenyl-isoxazol-4-one 
• 64-19-7 acetic acid 
• 29313-18-6 N-nitroso-benzanilide 

Downstream Products

• 3027-01-8 N,N-dibenzoylaniline 
• 2556-46-9 N,N'-diphenylbenzamidine 
• 2866-82-2 N-(4-chlorophenyl)benzamide 
• 1020-39-9 N-(2-chlorophenyI)benzamide 
• 100961-09-9 N-benzoyl-N-dichloroacetyl-aniline 
• 14805-58-4 N,N'-dibenzoyl-N,N'-diphenyl-oxalamide 
• 20349-66-0 (4‐(methyl(phenyl)amino)phenyl)(phenyl)methanone 
• 1015-89-0 6(5H)-phenanthridinone 
• 883-93-2 2-Phenylbenzothiazole 
• 32586-68-8 2-phenylbenzo[d][1,3]selenazole 
• 1015-89-0 phenanthridin-6-ol 
• 7477-73-8 1,5-diphenyltetrazole 
• 4771-08-8 N-(3-nitrophenyl)benzamide 
• 7702-38-7 N-(4-bromophenyl)benzamide 

Relevant articles and documents

Proton-Transfer Spectroscopy of Benzanilide. The Amide-Imidol Tautomerism

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Synthesis and characterization of nano-cellulose immobilized phenanthroline-copper (I) complex as a recyclable and efficient catalyst for preparation of diaryl ethers, N-aryl amides and N-aryl heterocycles

Functionalized nanocellulose was prepared and employed for immobilization of phenanthroline-copper(I) complex to afford cellulose nanofibril grafted heterogeneous copper catalyst [CNF-phen-Cu(I)]. This nanocatalyst was well characterized using FT-IR, NMR, XRD, CHNS, AAS, TGA, EDX and SEM. The activities of the synthesized catalyst were examined in the synthesis of diaryl ethers via C-O cross-coupling of phenols and aryl iodides, as well as, the preparation of N-aryl amides and N-aryl heterocycles through C-N cross-coupling of amides and N-H heterocycle compounds with aryl halides. In this trend, various substrates containing electron-donating and electron-withdrawing groups were exploited to evaluate the generality of this catalytic protocol. Accordingly, the catalyst demonstrated remarkable catalytic efficiency for both C-N and C-O cross-coupling reactions, thereby resulting in good to excellent yields of the desired products. Furthermore, the recoverability experiments of the catalyst showed that it can be readily retrieved by simple filtration and successfully reused several times with negligible loss of its catalytic activity.

TBAI-catalyzed C–N bond formation through oxidative coupling of benzyl bromides with amines: a new avenue to the synthesis of amides

A new green approach for the synthesis of amide through TBAI-catalyzed oxidative coupling of benzyl bromides with amine was developed in the presence of tert-butyl hydroperoxide (TBHP) as an oxidant. Various electron-donating and withdrawing groups containing benzyl bromides and various amines, were subjected to the reaction and transformed to the corresponding amide in good to excellent yields.