2-Chloro-6-nitroaniline

Base Information

• Chemical Name: 2-Chloro-6-nitroaniline
• CAS No.: 769-11-9
• Molecular Formula: C6H5ClN2O2
• Molecular Weight: 172.571
• Hs Code.: 2921420090
• European Community (EC) Number: 212-204-9
• NSC Number: 37398
• UNII: R43Y9JM7M3
• DSSTox Substance ID: DTXSID60227690
• Nikkaji Number: J140.779A
• Wikidata: Q22829117
• Mol file: 769-11-9.mol

Synonyms:2-Chloro-6-nitroaniline;769-11-9;2-Chloro-6-nitro-phenylamine;6-Chloro-2-nitroaniline;Benzenamine, 2-chloro-6-nitro-;Aniline, 2-chloro-6-nitro-;EINECS 212-204-9;MFCD00179568;NSC-37398;2-Chloro-6-nitro aniline;Benzenamine,2-chloro-6-nitro-;NSC37398;2-nitro-6-chloroaniline;2-Chloro-6-nitrobenzenamine;SCHEMBL213882;R43Y9JM7M3;DTXSID60227690;CL8396;NSC 37398;STL119729;AKOS000113873;AB04408;DS-0495;PS-4459;AC-11899;SY015647;2-Chloro-6-nitro-phenylamine, AldrichCPR;AM20050590;BB 0244112;CS-0027051;FT-0600705;EN300-53473;A838893;W-203758;Z802556472

Chemical Property of 2-Chloro-6-nitroaniline

Chemical Property:

• Vapor Pressure: 0.003mmHg at 25°C
• Melting Point: 74-75 °C
• Refractive Index: 1.646
• Boiling Point: 284.3 °C at 760 mmHg
• PKA: pK1: 2.41(+1) (25°C)
• Flash Point: 125.8 °C
• PSA: 71.84000
• Density: 1.494 g/cm³
• LogP: 2.93480
• 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: 172.0039551
• Heavy Atom Count: 11
• Complexity: 159

Purity/Quality:

98% ^*data from raw suppliers

2-Chloro-6-nitroaniline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C(=C1)Cl)N)[N+](=O)[O-]

Technology Process of 2-Chloro-6-nitroaniline

There total 17 articles about 2-Chloro-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: 87.0%

1,2-Dichloro-3-nitrobenzene (3209-22-1) → 2-chloro-6-nitroaniline (769-11-9)

Guidance literature:

With ammonium hydroxide; In ethanol; at 100 ℃; for 24h; Autoclave;

DOI:10.1016/j.ejmech.2019.111748

Reference yield: 64.0%

o-azidonitrobenzene (1516-58-1) → 2-chloro-6-nitroaniline (769-11-9) + 2-nitro-aniline (88-74-4) + 4-Chloro-2-nitroaniline (89-63-4)

Guidance literature:

With boron trichloride; In benzene; Ambient temperature;

DOI:10.1039/c39830001065

Reference yield: 46.0%

3-Nitrochlorobenzene (121-73-3) → 2-chloro-6-nitroaniline (769-11-9)

Guidance literature:

With potassium tert-butylate; N-methoxylamine hydrochloride; copper(l) chloride; In N,N-dimethyl-formamide; for 1h;

DOI:10.1021/jm0300835

upstream raw materials:

1,2-Dichloro-3-nitrobenzene

N-(2-chloro-6-nitrophenyl)acetanilide

2,3-dinitrochlorobenzene

tert-butylhypochlorite

Downstream raw materials:

1-chloro-2-iodo-3-nitrobenzene

bis-(2-chloro-6-nitro-phenyl)-diazene

2-bromo-1-chloro-3-nitro-benzene

1,2-Dichloro-3-nitrobenzene

Refernces

• 1、 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.
• 2、 Sohn, Jungsan,Kiburz, Brendan,Li, Zhitao,Deng, Liu,Safi, Alexias,Pirrung, Michael C.,Rudolph, Johannes. "Inhibition of Cdc25 phosphatases by indolyldihydroxyquinones". . p. 2580 - 2588. Retrieved 2007/10/03.