2-Chloro-4-methyl-6-nitroaniline

Base Information

• Chemical Name: 2-Chloro-4-methyl-6-nitroaniline
• CAS No.: 5465-33-8
• Molecular Formula: C7H7ClN2O2
• Molecular Weight: 186.598
• Hs Code.: 2921430090
• European Community (EC) Number: 226-768-9
• NSC Number: 28974
• DSSTox Substance ID: DTXSID90203109
• Nikkaji Number: J210.535G
• Wikidata: Q83076468
• Mol file: 5465-33-8.mol

Synonyms:2-chloro-4-methyl-6-nitroaniline;5465-33-8;2-CHLORO-4-METHYL-6-NITRO-PHENYLAMINE;2-Chloro-6-nitro-p-toluidine;EINECS 226-768-9;NSC28974;Benzenamine, 2-chloro-4-methyl-6-nitro-;SCHEMBL8574365;DTXSID90203109;AMY17108;MFCD08059084;NSC 28974;NSC-28974;AKOS017515336;s10853;(2-chloro-4-methyl-6-nitrophenyl)amine;BS-17048;CS-0153376;FT-0705341;EN300-180038;A830293;F8885-0221

Chemical Property of 2-Chloro-4-methyl-6-nitroaniline

Chemical Property:

• Vapor Pressure: 0.000717mmHg at 25°C
• Melting Point: 63-65 °C
• Refractive Index: 1.627
• Boiling Point: 307.6 °C at 760 mmHg
• PKA: -1.62±0.25(Predicted)
• Flash Point: 139.8 °C
• PSA: 71.84000
• Density: 1.415 g/cm³
• LogP: 3.24320
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 186.0196052
• Heavy Atom Count: 12
• Complexity: 183

Purity/Quality:

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

2-Chloro-4-methyl-6-nitroaniline 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=C(C(=C1)Cl)N)[N+](=O)[O-]
• Uses: 2-Chloro-4-methyl-6-nitroaniline is a useful reagent in the preparation of phenylalanines as selective AMPA and kainate receptor ligands.

Technology Process of 2-Chloro-4-methyl-6-nitroaniline

There total 5 articles about 2-Chloro-4-methyl-6-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: 95.0%

2-chloro-4-methyl-benzenamine (615-65-6) → 2-chloro-4-methyl-6-nitroaniline (5465-33-8)

Guidance literature:

With 4-nitro-4-methyl-2,3,5,6-tetrabromo-2,5-cyclohexadien-1-one; In trifluoroacetic acid; for 3h; Ambient temperature;

DOI:10.1055/s-1989-27387

Reference yield: 29.0%

4-methyl-2-nitroaniline (89-62-3) → 2-chloro-4-methyl-6-nitroaniline (5465-33-8)

Guidance literature:

With N-chloro-succinimide; In acetonitrile; Heating;

DOI:10.1021/jm000199q

Reference yield:

N-(2-chloro-4-methylphenyl)acetamide (18931-78-7) → 2-chloro-4-methyl-6-nitroaniline (5465-33-8)

Guidance literature:

With nitric acid; at 20 ℃; man verseift das Acetylderivat mit Schwefelsaeure;

upstream raw materials:

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

4-methyl-2-nitroaniline

2-chloro-4-methyl-benzenamine

nitric acid

Downstream raw materials:

4-iodo-3-chloro-5-nitro-toluene

acetylamino-(3,4-dichloro-benzyl)-malonic acid diethyl ester

2,3-dichloro-5-methylphenylamine

(RS)-5-(5-(2-amino-2-carboxyethyl)-2,3-dichlorophenyl)thiophene-2-carboxylic acid

Refernces

• 1、 Grella,Danso-Danquah,Safo,Joshi,Kister,Marden,Hoffman,Abraham. "Synthesis and structure - Activity relationships of chiral allosteric modifiers of hemoglobin". . p. 4726 - 4737. Retrieved 2007/10/03.
• 2、 Lemaire, M.,Guy, A.,Boutin, P.,Guette, J. P.. "Direct Nitration of Anilines Using Nitrocyclohexadienones". . p. 761 - 763. Retrieved 2007/10/02.