3,5-Dichloro-4-nitroaniline

Base Information

• Chemical Name: 3,5-Dichloro-4-nitroaniline
• CAS No.: 59992-52-8
• Molecular Formula: C₆H₄Cl₂N₂O₂
• Molecular Weight: 207.016
• DSSTox Substance ID: DTXSID00396359
• Nikkaji Number: J141.330I
• Wikidata: Q82197026
• Mol file: 59992-52-8.mol

Synonyms:3,5-dichloro-4-nitroaniline;59992-52-8;3,5-Dichlor-4-nitroanilin;SCHEMBL6673368;DTXSID00396359;STK365411;Benzenamine, 3,5-dichloro-4-nitro-;AKOS005442625

Chemical Property of 3,5-Dichloro-4-nitroaniline

Chemical Property:

• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 205.9649828
• Heavy Atom Count: 12
• Complexity: 173

Purity/Quality:

99% ^*data from raw suppliers

3,5-Dichloro-4-nitroaniline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=C(C=C(C(=C1Cl)[N+](=O)[O-])Cl)N
• Uses: 3,5-Dichloro-4-nitroaniline can be used as modulators of nuclear hormone receptor function.

Technology Process of 3,5-Dichloro-4-nitroaniline

There total 6 articles about 3,5-Dichloro-4-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: 86.0%

2,4,6-trichloronitrobenzene (18708-70-8) → 3,5-dichloro-2-nitroaniline (122584-83-2) + 2,6-dichloro-4-aminonitrobenzene (59992-52-8)

Guidance literature:

2,4,6-trichloronitrobenzene; With sodium azide; In dimethyl sulfoxide; at 20 ℃; for 20h;

With sodium tetrahydroborate; copper(II) sulfate; In ethanol; dichloromethane; at 20 ℃; for 1h;

DOI:10.1021/jm061410m

Reference yield:

1-(2,4-dichloro-3-nitrophenyl)pyridin-1-ium trifluoromethanesulfonate → 2,6-dichloro-4-aminonitrobenzene (59992-52-8) + 2,4-dichloro-3-nitroaniline (129825-24-7)

Guidance literature:

With piperidine; In acetonitrile; at 20 ℃; for 14h; Overall yield = 68 mg; Sealed tube; Inert atmosphere;

DOI:10.1002/anie.201810261

Reference yield:

2,6-dichloronitrobenzene (601-88-7) → 2,6-dichloro-4-aminonitrobenzene (59992-52-8) + 2,4-dichloro-3-nitroaniline (129825-24-7)

Guidance literature:

Multi-step reaction with 2 steps

1: tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate / acetonitrile / 1.5 h / Sealed tube; Schlenk technique; Inert atmosphere; Irradiation

2: piperidine / acetonitrile / 14 h / 20 °C / Sealed tube; Inert atmosphere

With piperidine; tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; In acetonitrile;

DOI:10.1002/anie.201810261

upstream raw materials:

N-(3,5-dichlorophenyl)-acetamide

2,4,6-trichloronitrobenzene

2,6-dichloronitrobenzene

Downstream raw materials:

4-nitro-2,6-dichloroaniline

2,6-dichloro-p-phenylenediamine

acetic acid-(3,5-dichloro-4-nitro-anilide)

4'-cyano-3,5-dichloro-2',4,6'-trinitrodiphenylamine

Refernces

• 1、 Giannouli, Vasiliki,Kostakis, Ioannis K.,Pouli, Nicole,Marakos, Panagiotis,Kousidou, Olga Ch.,Tzanakakis, George N.,Karamanos, Nikos K.. "Design, synthesis, and evaluation of the antiproliferative activity of a series of novel fused xanthenone aminoderivatives in human breast cancer cells". . p. 1716 - 1719. Retrieved 2007/10/03.