4'-cyanobenzanilide

Base Information

• Chemical Name: 4'-cyanobenzanilide
• CAS No.: 10278-46-3
• Molecular Formula: C14H10 N2 O
• Molecular Weight: 222.246
• Hs Code.: 2926909090
• European Community (EC) Number: 233-623-3
• UNII: HEJ7AD7TPX
• DSSTox Substance ID: DTXSID80145504
• Nikkaji Number: J236.739D
• Wikidata: Q83010069
• Mol file: 10278-46-3.mol

Synonyms:Benzanilide,4'-cyano- (7CI,8CI); 4'-Cyanobenzanilide; N-(4-Cyanophenyl)benzamide;p-Benzamidobenzonitrile

Chemical Property of 4'-cyanobenzanilide

Chemical Property:

• Boiling Point: 314.9oC at 760 mmHg
• Flash Point: 144.2oC
• PSA: 52.89000
• Density: 1.22g/cm3
• LogP: 2.88358
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 222.079312947
• Heavy Atom Count: 17
• Complexity: 303

Purity/Quality:

98%,99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(=O)NC2=CC=C(C=C2)C#N

Technology Process of 4'-cyanobenzanilide

There total 49 articles about 4'-cyanobenzanilide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

4-iodobenzonitrile (3058-39-7) + benzamide (55-21-0,27208-38-4) → N-(4-cyanophenyl)benzamide (10278-46-3)

Guidance literature:

With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In tetrahydrofuran; at 45 ℃; for 18h;

DOI:10.1021/ja012610k

Reference yield: 98.0%

benzoic acid methyl ester (93-58-3,5705-52-2,80226-58-0) + 4-Aminobenzonitrile (873-74-5) → N-(4-cyanophenyl)benzamide (10278-46-3)

Guidance literature:

With sodium t-butanolate; In neat (no solvent); at 20 ℃; for 1h; Inert atmosphere; Schlenk technique; Green chemistry;

DOI:10.1039/d1gc00720c

Reference yield: 96.0%

benzoyl chloride (98-88-4) + 4-Aminobenzonitrile (873-74-5) → N-(4-cyanophenyl)benzamide (10278-46-3)

Guidance literature:

With N,N-dimethyl acetamide; at 0 - 23 ℃; for 2h; Green chemistry;

DOI:10.1055/s-0037-1609342

upstream raw materials:

benzoyl chloride

4-Aminobenzonitrile

carbon monoxide

benzene

Downstream raw materials:

N-(4-cyano-phenyl)-benzimidoyl chloride

2-(benzyloxy)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

2-phenylbenzo[d]oxazole-6-carbonitrile

N-[4-(1H-tetrazole-5-yl)phenyl]benzamide

Refernces

• 1、 Li, Min-Xin,Li, Mei-Ling,Tang, Yan-Ling,Sun, Yun,Qu, Lu,Huang, Feng,Mao, Ze-Wei. "Exploration of Cu-catalyzed regioselective hydrodehalogenation of o-haloanilides using EtOH as hydrogen source". . . Retrieved 2021.
• 2、 Shugrue,Defrancisco,Metrano,Brink,Nomoto,Linton. "Detection of weak hydrogen bonding to fluoro and nitro groups in solution using H/D exchange". . p. 2223 - 2227. Retrieved 2016.
• 3、 Wang, Zhen,Kuninobu, Yoichiro,Kanai, Motomu. "Molybdenum-mediated desulfurization of dhiols and disulfides". . p. 1869 - 1872. Retrieved 2014.
• 4、 Wu, Xinghua,Hu, Longqin. "Amide bond formation from selenocarboxylates and aromatic azides". . p. 8401 - 8405. Retrieved 2005.
• 5、 Yadav, Deepika,Awasthi, Satish Kumar. "An unsymmetrical covalent organic polymer for catalytic amide synthesis". . p. 179 - 186. Retrieved 2019.
• 6、 Sharma, Pallavi,Moorhouse, Adam D.,Moses, John E.. "Microwave-enhanced reaction of thioacids with azides in aqueous medium". . p. 2384 - 2386. Retrieved 2011.
• 7、 McGuire, Ryan T.,Paffile, Julia F. J.,Zhou, Yuqiao,Stradiotto, Mark. "Nickel-Catalyzed C-N Cross-Coupling of Ammonia, (Hetero)anilines, and Indoles with Activated (Hetero)aryl Chlorides Enabled by Ligand Design". . p. 9292 - 9297. Retrieved 2019.
• 8、 Chen, Cheng,Cheng, Hua,Du, Min-Chen,Qian, Liang,Qin, Xin,Sang, Wei,Yao, Wei-Zhong,Yuan, Ye,Zhang, Rui. "A practical and sustainable protocol for direct amidation of unactivated esters under transition-metal-free and solvent-free conditions". supporting information. p. 3972 - 3982. Retrieved 2021/06/17.