3-Chloroaniline

Base Information

• Chemical Name: 3-Chloroaniline
• CAS No.: 108-42-9
• Deprecated CAS: 1083238-51-0
• Molecular Formula: C6H6ClN
• Molecular Weight: 127.573
• Hs Code.: 2921.42
• European Community (EC) Number: 203-581-0
• ICSC Number: 0130
• NSC Number: 17581
• UN Number: 2019
• UNII: 6GKR52SKIY
• DSSTox Substance ID: DTXSID0024761
• Nikkaji Number: J2.759.604E,J2.422H
• Wikidata: Q2497496
• ChEMBL ID: CHEMBL325415
• Mol file: 108-42-9.mol

Synonyms:3-chloroaniline;3-chloroaniline hydrochloride;m-chloroaniline;meta-chloroaniline

Chemical Property of 3-Chloroaniline

Chemical Property:

• Appearance/Colour: clear pale yellow to brown liquid
• Vapor Pressure: 1 mm Hg ( 63.5 °C)
• Melting Point: -11--9 °C(lit.)
• Refractive Index: 1.5941
• Boiling Point: 227.8 °C at 760 mmHg
• PKA: 3.46(at 25℃)
• Flash Point: 123.9 °C
• PSA: 26.02000
• Density: 1.216
• LogP: 2.50340
• Storage Temp.: Store below +30°C.
• Solubility.: 6.2g/l
• Water Solubility.: 6.8 g/L (20 ºC)
• 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: 74.9
• Transport DOT Label: Poison

Purity/Quality:

99%min ^*data from raw suppliers

3-?Chloroaniline(3-Chlorobenzenamine) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,N
• Hazard Codes: T,N
• Statements: 23/24/25-33-50/53
• Safety Statements: 28-36/37-45-60-61-28A

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Amines, Aromatic
• Canonical SMILES: C1=CC(=CC(=C1)Cl)N
• Inhalation Risk: No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
• Effects of Short Term Exposure: The substance is irritating to the eyes and skin. The substance may cause effects on the blood. This may result in the formation of methaemoglobin. Medical observation is indicated. The effects may be delayed.
• Effects of Long Term Exposure: The substance may have effects on the blood. This may result in the formation of methaemoglobin.
• Uses: 3-Chlorobenzenamine is used in the synthesis of pyrimidoazepine analogs as serotonin 5-HT2A and 5-HT2C receptor ligands for the treatment of obesity. Also used in the synthesis of novel COX-2 inhibito rs.

Technology Process of 3-Chloroaniline

There total 144 articles about 3-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: 81.4%

3-Nitrochlorobenzene (121-73-3) → aniline (62-53-3) + 3-chloro-aniline (108-42-9) + 3,3'-dichloroazobenzene (15426-14-9,106131-20-8,106131-24-2) + 3,3'-dichloroazoxybenzene (139-24-2,71297-98-8)

Guidance literature:

With bis(acetylacetonato)palladium(II); phosphorus; hydrogen; In N,N-dimethyl-formamide; benzene; at 50 ℃; for 1.75h; under 1520.1 Torr; Time; chemoselective reaction; Catalytic behavior;

DOI:10.1134/S0023158417010104

Reference yield: 81.0%

3-Nitrochlorobenzene (121-73-3) → aniline (62-53-3) + 3-chloro-aniline (108-42-9)

Guidance literature:

With Rh/Al₂O₃; hydrogen; In water; toluene; at 80 ℃; for 24h; under 30003 Torr; Reagent/catalyst;

DOI:10.1016/j.catcom.2016.05.016

Reference yield: 60.0%

3,3'-dichloroazoxybenzene (139-24-2,71297-98-8) + sodium thiomethoxide (5188-07-8) → Dimethyldisulphide (624-92-0) + 3-Chloro-4-methylsulfanyl-phenylamine (5211-01-8) + 3-chloro-aniline (108-42-9)

Guidance literature:

In isopropyl alcohol; for 1h; Heating;

DOI:10.1016/S0040-4039(00)76537-3

upstream raw materials:

1-methyl-4-nitrosobenzene

3-chloro-benzoic acid bromoamide

3-Nitrochlorobenzene

m-chlorophenylbiguanide hydrochloride

Downstream raw materials:

6-oxo-6H-pyran-2-carboxylic acid-(3-chloro-anilide)

2-amino-N-(3-chlorophenyl)benzamide

2-(3-chloro-phenyl)-4-nitro-isoindoline-1,3-dione

4,5,6,7-tetrachloro-2-(3-chloro-phenyl)-isoindoline-1,3-dione

Refernces

Halogen bonding synthon modularity in coordination compounds

10.1021/acs.cgd.5b00282

The research aims to understand how the crystal structure of [HgBr2(L3,4?diCl)] is influenced by its single-component precursors [HgBr2(L3?Cl)] and [HgBr2(L4?Cl)], where L represents a N-(chlorinatedphenyl)-2-pyrazinecarboxamide ligand. The researchers found that the crystal packing of [HgBr2(L3,4?diCl)] retains the Cl···N and Cl···Br halogen bonding synthons reminiscent of the single components, demonstrating structural modularity based on halogen bonding interactions. This is the first report on structural modularity in coordination compounds and could be instrumental in inorganic crystal engineering, particularly in polymorphism and crystal structure prediction. The chemicals used in the process include 3-chloroaniline, 4-chloroaniline, 3,4-dichloroaniline, pyrazinecarboxylic acid, and HgBr2.