N-(4-Chlorophenyl)-2-nitroaniline

Base Information

• Chemical Name: N-(4-Chlorophenyl)-2-nitroaniline
• CAS No.: 23008-56-2
• Molecular Formula: C12H9ClN2O2
• Molecular Weight: 248.669
• Hs Code.: 2921440000
• European Community (EC) Number: 245-377-4
• UNII: XSJ8CPM4LS
• DSSTox Substance ID: DTXSID00177564
• Nikkaji Number: J37.805D
• Wikidata: Q83047890
• Mol file: 23008-56-2.mol

Synonyms:N-(4-Chlorophenyl)-2-nitroaniline;23008-56-2;4-Chloro-2'-nitrodiphenylamine;N-(4-Chlorophenyl)-2-nitrobenzenamine;2-(4-Chlorophenylamino)nitrobenzene;2-Nitro-4'-chlorodiphenylamine;EINECS 245-377-4;2-(4-Chlorophenylamino)-1-nitrobenzene;Benzenamine, N-(4-chlorophenyl)-2-nitro-;Benzenamine,N-(4-chlorophenyl)-2-nitro-;XSJ8CPM4LS;2-Nitro-4'-chlordiphenylamin;SCHEMBL247794;4'-Chloro-2-nitrodiphenylamin;4'-Chloro-2-nitrodiphenylamine;DTXSID00177564;2-(4-chloroanilino)-nitrobenzene;MFCD02683544;STL481290;AKOS015914915;2-Nitro-4'-chlorodiphenylamine, 98%;4-Chloro-N-(2-nitrophenyl)benzenamine;DS-6268;AC-10682;C.I.10336;N-(4-chlorophenyl)-N-(2-nitrophenyl)amine;CS-0156624;FT-0658139;A816481;Q-200451

Chemical Property of N-(4-Chlorophenyl)-2-nitroaniline

Chemical Property:

• Melting Point: 145-148 °C(lit.)
• Boiling Point: 377.219 °C at 760 mmHg
• PKA: -3.90±0.40(Predicted)
• Flash Point: 181.936 °C
• PSA: 57.85000
• Density: 1.387 g/cm³
• LogP: 4.58800
• Storage Temp.: 2-8°C(protect from light)
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 248.0352552
• Heavy Atom Count: 17
• Complexity: 262

Purity/Quality:

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

2-?Nitro-?4''-?chlorodiphenylamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C(=C1)NC2=CC=C(C=C2)Cl)[N+](=O)[O-]
• Uses: 2-?Nitro-?4''-?chlorodiphenylamine is a reagent used in the synthesis of novel 4-phenoxyquinoline derivatives as c-Met kinase inhibitors. Intermediate for Clofazimine.

Technology Process of N-(4-Chlorophenyl)-2-nitroaniline

There total 8 articles about N-(4-Chlorophenyl)-2-nitroaniline 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: 96.0%

4-chloro-aniline (106-47-8) + ortho-nitrofluorobenzene (1493-27-2,127723-77-7) → N-(4-chlorophenyl)-2-nitroaniline (23008-56-2)

Guidance literature:

With triethylamine; In neat (no solvent); at 140 ℃; for 9h;

DOI:10.1016/j.tetlet.2020.151599

Reference yield: 95.0%

2-nitrophenylboronic acid (5570-19-4) + 4-chloro-aniline (106-47-8) → N-(4-chlorophenyl)-2-nitroaniline (23008-56-2)

Guidance literature:

With potassium fluoride; In dimethyl sulfoxide; at 130 ℃; for 2h; Inert atmosphere;

DOI:10.1007/s11164-019-03760-0

Reference yield: 80.0%

4-chloro-aniline (106-47-8) + 2-Chloronitrobenzene (88-73-3) → N-(4-chlorophenyl)-2-nitroaniline (23008-56-2)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; at 80 ℃; for 1h;

DOI:10.1081/SCC-120022180

upstream raw materials:

2-nitro-N-phenylaniline

sodium acetate

4-chloro-aniline

2-Chloronitrobenzene

Downstream raw materials:

2,4-dinitro-4'-chloro diphenylamine

1-(4-chlorophenyl)-1,3-dihydro-2H-benzoimidazol-2-one

ethyl 4-(4-chlorophenyl)-3-oxo-3,4-dihydroquinoxaline-2-carboxylate

C₁₉H₁₉ClN₄

Refernces

• 1、 Xu, Zhi-Bin,Lu, Ying,Guo, Zong-Ru. "An efficient and fast procedure for the preparation of 2-nitrophenylamines under microwave conditions". . p. 564 - 566. Retrieved 2003.
• 2、 Cui, Jian-Lan,Wang, Ning,Wang, Xiao,Yu, Si-Yuan,Zhong, Cong-Shan. "A green and practical reduction of N-(4-chlorophenyl)-2-nitroaniline and its derivatives to corresponding N-substituted-benzene-1,2-diamines using thiourea dioxide". supporting information. . Retrieved 2020/01/22.
• 3、 Qi, Xinxin,Zhou, Rong,Peng, Jin-Bao,Ying, Jun,Wu, Xiao-Feng. "Selenium-Catalyzed Carbonylative Synthesis of 2-Benzimidazolones from 2-Nitroanilines with TFBen as the CO Source". supporting information. p. 5161 - 5164. Retrieved 2019/01/25.