4-Chloroaniline

Base Information

• Chemical Name: 4-Chloroaniline
• CAS No.: 106-47-8
• Molecular Formula: C6H6ClN
• Molecular Weight: 127.573
• Hs Code.: 2921.42
• European Community (EC) Number: 203-401-0
• ICSC Number: 0026
• NSC Number: 36941
• UN Number: 2018
• UNII: Z553SGH315
• DSSTox Substance ID: DTXSID9020295
• Nikkaji Number: J2.759.605C,J4.034G
• Wikipedia: 4-Chloroaniline
• Wikidata: Q413515
• Metabolomics Workbench ID: 51281
• ChEMBL ID: CHEMBL15888
• Mol file: 106-47-8.mol

Synonyms:4-chloroaniline;4-chloroaniline hydrochloride;4-chloroaniline, trifluoroboron salt (1:1);p-chloroaniline;p-chlorophenylamine;para-chloroaniline

Chemical Property of 4-Chloroaniline

Chemical Property:

• Appearance/Colour: Clear amber liquid
• Vapor Pressure: 0.209mmHg at 25°C
• Melting Point: 67-70 °C(lit.)
• Refractive Index: 1.5546
• Boiling Point: 174.1 °C at 760 mmHg
• PKA: 4.15(at 25℃)
• Flash Point: 60.7 °C
• PSA: 26.02000
• Density: 1.23 g/cm³
• LogP: 2.50340
• Storage Temp.: 2-8°C
• Solubility.: 2.2g/l
• Water Solubility.: 0.3 g/100 mL (20℃)
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 127.0188769
• Heavy Atom Count: 8
• Complexity: 66.9
• Transport DOT Label: Poison

Purity/Quality:

99% ^*data from raw suppliers

4-?Chloroaniline(4-Chlorophenylamine) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T，N，F
• Hazard Codes: T:Toxic;;
• Statements: R23/24/25:; R43:; R45:; R50/53:
• Safety Statements: S45:; S53:; S60:; S61:

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Amines, Aromatic
• Canonical SMILES: C1=CC(=CC=C1N)Cl
• Inhalation Risk: A harmful concentration of airborne particles can be reached quickly when dispersed.
• Effects of Short Term Exposure: The substance is irritating to the eyes. The substance may cause effects on the red blood cells. This may result in lesions of blood cells and the formation of methaemoglobin. Medical observation is indicated. The effects may be delayed.
• Effects of Long Term Exposure: Repeated or prolonged contact may cause skin sensitization. The substance may have effects on the spleen. Tumours have been detected in experimental animals but may not be relevant to humans.
• Physical properties: Yellowish-white solid with a mild, sweetish odor. Odor threshold concentration is 287 ppm (quoted, Keith and Walters, 1992).
• Uses: 4-Chloroaniline is an important raw material in production of agricultural chemicals, azo dyes and pigments, cosmetics, and pharmaceutical products. It is used as an intermediate in the manufacture of chromophore AS-LB, as well as in pharmaceutical intermediates such as chlordiazepoxide and phena tincture. It is also an intermediate for the herbicide Anilofos, the insecticide chlorbenzuron and the plant growth regulator Inabenfide.

Technology Process of 4-Chloroaniline

There total 524 articles about 4-Chloroaniline 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: 68.0%

bromochlorobenzene (106-39-8) → bis(4-chlorophenyl)amine (6962-04-5) + 4-chloro-aniline (106-47-8)

Guidance literature:

With lithium amide; (CyPF-t-Bu)PdCl₂; In 1,2-dimethoxyethane; at 60 ℃; for 20h;

DOI:10.1021/ja064005t

Reference yield: 42.0%

N-(4-chlorophenyl)acetamide (539-03-7) → 2-amino-5-chloroacetophenone (1685-19-4) + 4-chloro-aniline (106-47-8)

Guidance literature:

In cyclohexane; at 25 ℃; Inert atmosphere; Irradiation;

DOI:10.1039/c5pp00349k

Reference yield: 17.0%

4-Cyanochlorobenzene (623-03-0) + 4-chlorobenzonitrile (100-00-5) → 4-chlorobenzanilide (6833-15-4) + 4,4'-dichlorobenzanilide (39193-06-1) + 4-chloro-aniline (106-47-8) + aniline (62-53-3)

Guidance literature:

With 9,10-dihydroanthracene; water; at 356.85 ℃; for 3h; Kinetics;

DOI:10.1021/jo0265885

upstream raw materials:

bromochlorobenzene

1-methyl-4-nitrosobenzene

4-chloro-benzoic acid bromoamide

2-methyl-5-nitro-N-phenylbenzenesulfonamide

Downstream raw materials:

N,N-bis(2-hydroxyethyl)-p-chloroaniline

2-(4-chloro-anilino)-ethanethiol

2,5-Bis(p-chlorophenyl)thiophene

2-(4-chlorophenyl)thiophene

Refernces

• 1、 Yadav, Veena,Gupta, Shweta,Kumar, Rupesh,Singh, Gajendra,Lagarkha, Rekha. "Polymeric PEG35k-Pd nanoparticles: Efficient and recyclable catalyst for reduction of nitro compounds". . p. 213 - 222. Retrieved 2012.
• 2、 Makaryan, I. A.. "CONVERSION OF N-ARYLHYDROXYLAMINES IN THE PRESENCE OF METAL COMPLEXES AND HETEROGENEOUS CATALYSTS". . p. 2569 - 2570. Retrieved 1988.
• 3、 Thomas, Christopher,Wu, Marvin,Billingsley, Kelvin L.. "Amination-Oxidation Strategy for the Copper-Catalyzed Synthesis of Monoarylamines". . p. 330 - 335. Retrieved 2016.
• 4、 Taheri-Ledari, Reza,Rahimi, Jamal,Maleki, Ali,Shalan, Ahmed Esmail. "Ultrasound-assisted diversion of nitrobenzene derivatives to their aniline equivalents through a heterogeneous magnetic Ag/Fe3O4-IT nanocomposite catalyst". . p. 19827 - 19835. Retrieved 2020.
• 5、 Lu, Chunshan,Wang, Mengjun,Feng, Zhenlong,Qi, Yani,Feng, Feng,Ma, Lei,Zhang, Qunfeng,Li, Xiaonian. "A phosphorus-carbon framework over activated carbon supported palladium nanoparticles for the chemoselective hydrogenation of para-chloronitrobenzene". . p. 1581 - 1589. Retrieved 2017.
• 6、 Li, Xin,Wang, Yue,Li, Liqun,Huang, Wenqing,Xiao, Zicheng,Wu, Pingfan,Zhao, Wenbo,Guo, Wei,Jiang, Peng,Liang, Minghui. "Deficient copper decorated platinum nanoparticles for selective hydrogenation of chloronitrobenzene". . p. 11294 - 11300. Retrieved 2017.
• 7、 McClelland, Robert A.,Kahley, Mary Jo,Davidse, P. Adriaan,Hadzialic, Gordana. "Acid-base properties of arylnitrenium ions". . p. 4794 - 4803. Retrieved 1996.
• 8、 Zhu, Zhongwei,Genaev, Alexander M.,Salnikov, George E.,Koltunov, Konstantin Yu.. "Superelectrophilic activation of 1-nitronaphthalene in the presence of aluminum chloride. Reactions with benzene and cyclohexane". . p. 9129 - 9132. Retrieved 2018.
• 9、 Pirkuliev,Brel,Akhmedov,Zefirov,Stang. "Xenon difluoride-trimethylsilyl isocyanate-triflic acid as a new system for the amination of aromatic compounds". . p. 172 - 173. Retrieved 2001.
• 10、 Bustamante, Tatiana M.,Dinamarca, Robinson,Torres, Cecilia C.,Pecchi, Gina,Campos, Cristian H.. "Pd-Co catalysts prepared from palladium-doped cobalt titanate precursors for chemoselective hydrogenation of halonitroarenes". . . Retrieved 2020.