4-chloro-N-phenylaniline

Base Information

• Chemical Name: 4-chloro-N-phenylaniline
• CAS No.: 1205-71-6
• Molecular Formula: C12H10ClN
• Molecular Weight: 203.671
• NSC Number: 231508
• DSSTox Substance ID: DTXSID70152883
• Nikkaji Number: J151.723F
• Wikidata: Q83019657
• Mol file: 1205-71-6.mol

Synonyms:4-chloro-N-phenylaniline;1205-71-6;4-Chlorodiphenylamine;Benzenamine, 4-chloro-N-phenyl-;4-CHLORO-N-PHENYLBENZENAMINE;N-Phenyl-4-chloroaniline;MFCD01027200;p-chlorophenylaniline;NSC231508;N(c1ccccc1)c2ccc(Cl)cc2;SCHEMBL1118626;DTXSID70152883;VPRIGCVCJPKVFZ-UHFFFAOYSA-N;BAA20571;AKOS000281448;NSC 231508;NSC-231508;SB78450;AM803033;BS-14559;SY126150;CS-0038965;A804539

Chemical Property of 4-chloro-N-phenylaniline

Chemical Property:

• Vapor Pressure: 0.000255mmHg at 25°C
• Melting Point: 74°C
• Refractive Index: 1.642
• Boiling Point: 323.8 °C at 760 mmHg
• PKA: 0.27±0.20(Predicted)
• Flash Point: 149.7 °C
• PSA: 12.03000
• Density: 1.216 g/cm³
• LogP: 4.15660
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 203.0501770
• Heavy Atom Count: 14
• Complexity: 158

Purity/Quality:

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

4-Chloro-N-phenylaniline 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)NC2=CC=C(C=C2)Cl

Technology Process of 4-chloro-N-phenylaniline

There total 84 articles about 4-chloro-N-phenylaniline 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%

4-chloro-aniline (106-47-8) + phenylboronic acid (98-80-6) → N-(4-chlorophenyl)aniline (1205-71-6)

Guidance literature:

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

DOI:10.1007/s11164-019-03760-0

Reference yield: 92.0%

4-chlorobenzonitrile (100-00-5) + phenylboronic acid (98-80-6) → N-(4-chlorophenyl)aniline (1205-71-6)

Guidance literature:

4-chlorobenzonitrile; With [2,2]bipyridinyl; [MoO₂Cl₂(dmf)₂]; In toluene; for 0.0333333h;

phenylboronic acid; With triphenylphosphine; In toluene; at 100 ℃; for 20h;

DOI:10.1002/anie.201812806

Reference yield: 88.0%

benzotriazol-1-ol (2592-95-2) + 4-chloro-aniline (106-47-8) → N-(4-chlorophenyl)aniline (1205-71-6)

Guidance literature:

With potassium hydroxide; In dimethyl sulfoxide; at 130 ℃; for 8h;

DOI:10.1007/s10562-018-2580-4

upstream raw materials:

(4-chloro-phenyl)-nitroso-phenyl-amine

4-chloro-aniline

bromobenzene

N-(4-chlorophenyl)acetamide

Downstream raw materials:

2-nitro-benzoic acid-[(4-chloro-phenyl)-phenyl-amide]

2-(2-(((1r,4r)-4-(((4-chlorophenyl)(phenyl)carbamoyloxy)methyl)cyclohexyl)methoxy)acetamido)ethanesulfonic acid

2-(((1r,4r)-4-(((4-chlorophenyl)(phenyl)carbamoyloxy)methyl)cyclohexyl)methoxy)acetic acid chloride

sodium 2-(((1r,4r)-4-(((4-chlorophenyl)(phenyl)carbamoyloxy)methyl)cyclohexyl)methoxy)acetate

Refernces

• 1、 Nakamura, Yuki,Ilies, Laurean,Nakamura, Eiichi. "Iron-catalyzed oxidative monoarylation of primary amines with organozinc reagents". . p. 5998 - 6001. Retrieved 2011.
• 2、 Veisi, Hojat,Ahmadian, Hossein,Mirshokraie, Seyed Ahmad,Didehban, Khadijeh,Zangeneh, Mohammad Mahdi. "CuCl2 heterogenized on metformine-modified polystyrene resin as an antibacterial agent and recyclable nanocatalyst for Ullmann-type C-N coupling reactions". . . Retrieved 2019.
• 3、 Khosravi, Armaqan,Mokhtari, Javad,Naimi-Jamal, Mohammad Reza,Tahmasebi, Sharareh,Panahi, Leila. "Cu2(BDC)2(BPY)-MOF: An efficient and reusable heterogeneous catalyst for the aerobic Chan-Lam coupling prepared via ball-milling strategy". . p. 46022 - 46027. Retrieved 2017.
• 4、 Veisi, Hojat,Hemmati, Saba,Javaheri, Hadis. "N-Arylation of indole and aniline by a green synthesized CuO nanoparticles mediated by Thymbra spicata leaves extract as a recyclable and heterogeneous nanocatalyst". . p. 3155 - 3159. Retrieved 2017.
• 5、 Walker, Benjamin R.,Manabe, Shuhei,Brusoe, Andrew T.,Sevov, Christo S.. "Mediator-Enabled Electrocatalysis with Ligandless Copper for Anaerobic Chan-Lam Coupling Reactions". supporting information. p. 6257 - 6265. Retrieved 2021/05/07.
• 6、 Yang, Fu,Dong, Xuexue,Shen, Yang,Liu, Mengting,Zhou, Hu,Wang, Xuyu,Li, Lulu,Yuan, Aihua,Song, Heng. "Reductive C?N Coupling of Nitroarenes: Heterogenization of MoO3 Catalyst by Confinement in Silica". . p. 3413 - 3421. Retrieved 2021/07/31.