99512-78-4

Basic information

• Product Name: 4-Nitro-3-trifluormethyldiphenylamin
• Synonyms: 4-Nitro-3-trifluormethyldiphenylamin
• CAS NO: 99512-78-4
• Molecular Weight: 282.222
• Mol File: 99512-78-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 4-Nitro-3-trifluormethyldiphenylamin(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Nitro-3-trifluormethyldiphenylamin(99512-78-4)
• EPA Substance Registry System: 4-Nitro-3-trifluormethyldiphenylamin(99512-78-4)

Safety Data

• Hazardous Substances Data: 99512-78-4(Hazardous Substances Data)

Upstream product

• 14933-91-6 N-phenyl-benzenesulphenamide 
• 384-22-5 2-nitrobenzotrifluoride 
• 393-09-9 4-fluoro-1-nitro-2-trifluoromethyl-benzene 
• 62-53-3 aniline 

Relevant articles and documents

Oxidative nucleophilic aromatic amination of nitrobenzenes

Nitrobenzenes substituted with electron-acceptor groups such as halogen, nitro, trifluoromethyl, pentafluorosulfanyl, or cyano underwent oxidative nucleophilic substitution with lithium salts of arylamines to afford N-aryl-2-nitroanilines.

Development of nonsteroidal antiandrogens: 4-Nitro-3-trifluoro-methyldiphenylamines

For the development of new nonsteroidal antiandrogens a series of 4-nitro-3-trifluoromethyldiphenylamines was synthesized and compounds were tested for their affinities to steroid hormone receptors and for antiandrogenic activities. These compounds were synthesized by reacting 4-nitro-3-trifluoromethylphenylsulfocyanamide-sodium (4) with the corresponding aromatic amines to give the N-(4-nitro-3-trifluoromethylphenylsulfonyl)-N'-phenylguanidines. The crude products were then converted to the desired diphenylamines by Smiles rearrangement and hydrolysis. 2-Hydroxy-4'-nitro-3'-trifluoromethyldiphenylamine (13), which shows a relative binding affinity (RBA) to the androgen receptor (AR) of 6.5% of that of testosterone, exerts a higher affinity than hydroxyflutamide (RBA = 4.5). Shift of the hydroxy-function to position 3 or 4 as well as N-methylation caused a decrease in AR-affinity. Compounds exerting AR-affinity were tested for antiandrogenic activity. Compound 13 showed the best antiandrogenic effect, though less than the well-known antiandrogen flutamide.