2-((4-Chloro-2-nitrophenyl)amino)benzoic acid

Base Information

• Chemical Name: 2-((4-Chloro-2-nitrophenyl)amino)benzoic acid
• CAS No.: 60091-87-4
• Molecular Formula: C13H9ClN2O4
• Molecular Weight: 292.678
• Hs Code.: 2922499990
• UNII: HB9LQ2397X
• DSSTox Substance ID: DTXSID40476386
• Wikidata: Q82307610
• Mol file: 60091-87-4.mol

Synonyms:60091-87-4;2-((4-Chloro-2-nitrophenyl)amino)benzoic acid;2-(4-chloro-2-nitroanilino)benzoic acid;2-[(4-Chloro-2-nitrophenyl)amino]-benzoic acid;2-[(4-chloro-2-nitrophenyl)amino]benzoic acid;2-(4-Chloro-2-nitrophenylamino)benzoic acid;Benzoic acid,2-[(4-chloro-2-nitrophenyl)amino]-;2-((4-Chloro-2-nitrophenyl)amino)benzoicacid;HB9LQ2397X;SCHEMBL2112961;DTXSID40476386;GBBIOGPNJFKJOD-UHFFFAOYSA-N;AKOS015961104;AB21115;AC-13019;AS-77412;2-(4-chloro-2-nitro-anilino)benzoic acid;N-(4-chloro-2-nitrophenyl)anthranilic acid;CS-0156706;D95007;Anthranilic acid, N-(4-chloro-2-nitrophenyl)-;A832593;Benzoic acid, 2-[(4-chloro-2-nitrophenyl)amino]-

Chemical Property of 2-((4-Chloro-2-nitrophenyl)amino)benzoic acid

Chemical Property:

• Vapor Pressure: 9.86E-09mmHg at 25°C
• Melting Point: 246-247 °C(Solv: ethanol (64-17-5))
• Refractive Index: 1.698
• Boiling Point: 445.9 °C at 760 mmHg
• PKA: 3.59±0.36(Predicted)
• Flash Point: 223.5 °C
• PSA: 95.15000
• Density: 1.525 g/cm³
• LogP: 4.28620
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Methanol (Slightly, Heated)
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 292.0250845
• Heavy Atom Count: 20
• Complexity: 374

Purity/Quality:

99% ^*data from raw suppliers

2-[(4-Chloro-2-nitrophenyl)amino]benzoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C(=C1)C(=O)O)NC2=C(C=C(C=C2)Cl)[N+](=O)[O-]
• Uses: 2-[(4-Chloro-2-nitrophenyl)amino]benzoic Acid is an diazepinomicin derivative with potential antcancer activity. 2-[(4-Chloro-2-nitrophenyl)amino]benzoic Acid is also an impurity in the synthesis of Clozepine, an antipsychotic. 2-[(4-Chloro-2-nitrophenyl)amino]benzoic Acid is an diazepinomicin derivative with potential antcancer activity. 2-[(4-Chloro-2-nitrophenyl)amino]benzoic Acid is also an impurity in the synthesis of Clozepine (C587500), an antipsychotic.

Technology Process of 2-((4-Chloro-2-nitrophenyl)amino)benzoic acid

There total 15 articles about 2-((4-Chloro-2-nitrophenyl)amino)benzoic acid 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: 97.0%

2-fluoro-5-chloronitrobenzene (345-18-6) + anthranilic acid (118-92-3,159201-01-1,50816-84-7,80206-34-4,104809-47-4) → 2-(4-Chlor-2-nitrophenyl)aminobenzencarbonsaeure (60091-87-4)

Guidance literature:

With caesium carbonate; In N,N-dimethyl-formamide; at 120 ℃;

DOI:10.1016/j.bmcl.2021.127911

Reference yield: 74.0%

ortho-nitrobenzoic acid (552-16-9,104810-18-6) + 2-chloro-5-bromonitrobenzene (41513-04-6) → 2-(4-Chlor-2-nitrophenyl)aminobenzencarbonsaeure (60091-87-4)

Guidance literature:

ortho-nitrobenzoic acid; 2-chloro-5-bromonitrobenzene; With copper; potassium carbonate; In i-Amyl alcohol; for 4h; Reflux;

With hydrogenchloride; In water;

Reference yield: 74.0%

2-chloro-5-bromonitrobenzene (41513-04-6) + anthranilic acid (118-92-3,159201-01-1,50816-84-7,80206-34-4,104809-47-4) → 2-(4-Chlor-2-nitrophenyl)aminobenzencarbonsaeure (60091-87-4)

Guidance literature:

With copper; potassium carbonate; In various solvent(s); for 4h; Heating;

DOI:10.1071/CH02093

upstream raw materials:

anthranilic acid

2,5-dichloronitrobenzene

2-chloro-5-bromonitrobenzene

2-fluoro-5-chloronitrobenzene

Downstream raw materials:

8,11-dichloro-5H-dibenzo[b,e][1,4]-diazepine

methyl 2-[(4-chloro-2-nitrophenyl)amino]benzoate

C₁₃H₈Cl₂N₂O₃

clozaril

Refernces

• 1、 Watanabe, Hitoshi,Ishida, Kyoji,Yamamoto, Masanori,Horiguchi, Masakuni,Isobe, Yoshiaki. "Synthesis and pharmacological evaluation of 11-(1,6-dimethyl-1,2,3,6-tetrahydropyridin-4-yl)-5H-dibenzo[b,e][1,4]diazepines with clozapine-like receptor occupancy at dopamine D1/D2 receptor". supporting information. . Retrieved 2020/10/02.
• 2、 Yu, Yongguo,Wu, Jianbo,Lei, Fan,Chen, Lei,Wan, Weili,Hai, Li,Guan, Mei,Wu, Yong. "Design, synthesis and anticancer activity evaluation of diazepinomicin derivatives". . p. 369 - 373. Retrieved 2013/07/26.