4-Chloro-2-nitroaniline

Base Information

• Chemical Name: 4-Chloro-2-nitroaniline
• CAS No.: 89-63-4
• Molecular Formula: C6H5ClN2O2
• Molecular Weight: 172.571
• Hs Code.: H3(NO2)NH2 MOL WT. 172.57
• European Community (EC) Number: 201-925-4
• NSC Number: 3546
• UN Number: 2237
• UNII: 1929LY233C
• DSSTox Substance ID: DTXSID4030384
• Nikkaji Number: J3.549A
• Wikidata: Q27252057
• ChEMBL ID: CHEMBL166405
• Mol file: 89-63-4.mol

Synonyms:4-chloro-2-nitroaniline

Chemical Property of 4-Chloro-2-nitroaniline

Chemical Property:

• Appearance/Colour: bright orange powder
• Vapor Pressure: 0.000667mmHg at 25°C
• Melting Point: 115-119 °C
• Refractive Index: 1.646
• Boiling Point: 308.8 °C at 760 mmHg
• PKA: pK1: 1.10(+1) (25°C)
• Flash Point: 140.5 °C
• PSA: 71.84000
• Density: 1.494 g/cm³
• LogP: 2.93480
• Storage Temp.: room temp
• Solubility.: 0.5g/l (anhydrous substance)
• Water Solubility.: INSOLUBLE
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 172.0039551
• Heavy Atom Count: 11
• Complexity: 159
• Transport DOT Label: Poison

Purity/Quality:

99% ^*data from raw suppliers

4-Chloro-2-nitroaniline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+, N, T
• Hazard Codes: T+,N,T
• Statements: 26/27/28-33-51/53
• Safety Statements: 28-36/37-45-61-28A

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitroanilines
• Canonical SMILES: C1=CC(=C(C=C1Cl)[N+](=O)[O-])N
• Uses: A nitro-aromatic amine with mutagenicity and carcinogenicity 4-Chloro-2-nitroaniline is used almost exclusively as an intermediate in the synthesis of pigments. The greatest potential for human exposure to 4-chloro-2- nitroaniline is in production and use of pigments made from the compound. 4-Chloro-2-nitroaniline is used as pharmaceutical intermediate.

Technology Process of 4-Chloro-2-nitroaniline

There total 71 articles about 4-Chloro-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: 99.2%

2-nitro-aniline (88-74-4) → 4-Chloro-2-nitroaniline (89-63-4)

Guidance literature:

With N-chloro-N-(benzenesulfonyl)benzenesulfonamide; In acetonitrile; at 20 - 25 ℃; for 0.0833333h; Green chemistry;

DOI:10.1016/j.tetlet.2020.152689

Reference yield: 99.0%

N-(2-nitro-4-chlorophenyl)benzamide (52010-24-9) → 4-Chloro-2-nitroaniline (89-63-4)

Guidance literature:

With potassium hydroxide; In methanol; at 20 ℃; for 12h;

DOI:10.1002/chem.201404000

Reference yield: 92.0%

4-chloro-aniline (106-47-8) → 4-Chloro-2-nitroaniline (89-63-4)

Guidance literature:

With nickel ammonium sulfate; nitric acid; In chloroform; water; at 20 ℃; for 3h;

DOI:10.1081/SCC-100103545

upstream raw materials:

piperidine

3-bromo-butyric acid-(4-chloro-2-nitro-anilide)

N-(4-chloro-2-nitrophenyl)-acetamide

2-fluoro-5-chloronitrobenzene

Downstream raw materials:

4-Chloro-2-nitrofumaranilic acid

4-chloro-2-nitrobenzonitrile

N,N'-bis-(4-chloro-2-nitro-phenyl)-urea

4-Oxo-4H-chromene-2-carboxylic acid (4-chloro-2-nitro-phenyl)-amide

Refernces

• 1、 Misal, Balu,Palav, Amey,Ganwir, Prerna,Chaturbhuj, Ganesh. "Activator free, expeditious and eco-friendly chlorination of activated arenes by N-chloro-N-(phenylsulfonyl)benzene sulfonamide (NCBSI)". supporting information. . Retrieved 2021/01/04.
• 2、 Rogers, David A.,Bensalah, Adam T.,Espinosa, Alvaro Tomas,Hoerr, John L.,Refai, Fares H.,Pitzel, Amy K.,Alvarado, Juan J.,Lamar, Angus A.. "Amplification of Trichloroisocyanuric Acid (TCCA) Reactivity for Chlorination of Arenes and Heteroarenes via Catalytic Organic Dye Activation". supporting information. p. 4229 - 4233. Retrieved 2019/06/17.