1,4-Naphthalenedione, 2-chloro-5-nitro-3-(phenylamino)-

Base Information

• Chemical Name: 1,4-Naphthalenedione, 2-chloro-5-nitro-3-(phenylamino)-
• CAS No.: 22360-48-1
• Molecular Formula: C₁₆H₉ClN₂O₄
• Molecular Weight: 328.711
• DSSTox Substance ID: DTXSID00479318
• Nikkaji Number: J2.141.970B
• Wikidata: Q82313303
• Mol file: 22360-48-1.mol

Synonyms:22360-48-1;1,4-Naphthalenedione, 2-chloro-5-nitro-3-(phenylamino)-;2-anilino-3-chloro-8-nitro-1,4-naphthoquinone;DTXSID00479318

Chemical Property of 1,4-Naphthalenedione, 2-chloro-5-nitro-3-(phenylamino)-

Chemical Property:

• XLogP3: 3.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 328.0250845
• Heavy Atom Count: 23
• Complexity: 563

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)NC2=C(C(=O)C3=C(C2=O)C(=CC=C3)[N+](=O)[O-])Cl

Technology Process of 1,4-Naphthalenedione, 2-chloro-5-nitro-3-(phenylamino)-

There total 2 articles about 1,4-Naphthalenedione, 2-chloro-5-nitro-3-(phenylamino)- 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:

2,3-dichloro-5-nitro-1,4-naphthoquinone (22360-86-7) + aniline (62-53-3) → 2-anilino-3-chloro-8-nitro-1,4-naphthoquinone (22360-48-1) + 2-anilino-3-chloro-5-nitro-1,4-naphthoquinone (22360-89-0)

Guidance literature:

aniline; With FDMP resin; sodium cyanoborohydride; acetic acid; In N,N-dimethyl-formamide; at 25 ℃; for 16h;

2,3-dichloro-5-nitro-1,4-naphthoquinone; With 2,6-di-tert-butyl-pyridine; In dichloromethane; at 25 ℃; for 2h;

With trifluoroacetic acid; In dichloromethane; at 25 ℃; for 0.25h; Title compound not separated from byproducts;

DOI:10.1016/j.tetlet.2005.01.049

Reference yield:

→ 2-anilino-3-chloro-8-nitro-1,4-naphthoquinone (22360-48-1)

Guidance literature:

Verb. /BRN= 884229/, Anilin, A., Rueckfluss (zwei Produkte);

Reference yield: 89.0%

2-anilino-3-chloro-8-nitro-1,4-naphthoquinone (22360-48-1) + 2-amino-benzenethiol (137-07-5) → 6-anilino-4-nitro-5H-benzophenothiazin-5-one (111680-50-3)

Guidance literature:

In pyridine;

DOI:10.1007/BF00809949

upstream raw materials:

2,3-dichloro-5-nitro-1,4-naphthoquinone

aniline

Downstream raw materials:

6-Anilino-11-aza-4-nitro-5H-benzo<6,5-a>phenoxazin-5-one

6-anilino-4-nitro-5H-benzophenothiazin-5-one

4-amino-6-anilino-5H-benzophenothiazin-5-one

4-acetylamino-6-anilino-5H-benzophenothiazin-5-one