86439-16-9

Basic information

• Product Name: 3-trifluoromethyl-5-phenyl-2,6-dicyanoaniline
• Synonyms: 3-trifluoromethyl-5-phenyl-2,6-dicyanoaniline
• CAS NO: 86439-16-9
• Molecular Weight: 287.244
• Mol File: 86439-16-9.mol

Chemical Properties

• CAS DataBase Reference: 3-trifluoromethyl-5-phenyl-2,6-dicyanoaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 3-trifluoromethyl-5-phenyl-2,6-dicyanoaniline(86439-16-9)
• EPA Substance Registry System: 3-trifluoromethyl-5-phenyl-2,6-dicyanoaniline(86439-16-9)

Safety Data

• Hazardous Substances Data: 86439-16-9(Hazardous Substances Data)

Upstream product

• 326-06-7 1-Phenyl-4,4,4-trifluorobutane-1,3-dione 
• 109-77-3 malononitrile 

Downstream Products

• 917234-37-8 3-amino-2-[imino(phenyl)methyl]-5-(trifluoromethyl)biphenyl-4-carbonitrile 
• 917234-39-0 3-amino-4-[imino(phenyl)methyl]-5-(trifluoromethyl)biphenyl-2-carbonitrile 
• 1256952-52-9 10-phenyl-5-(thiophen-2-yl)-8-(trifluoromethyl)-2,3-dihydroimidazo[1,2-c]quinazoline-7-carboxamide 
• 1256952-50-7 5-(4-hydroxyphenyl)-10-phenyl-8-(trifluoromethyl)-2,3-dihydroimidazo[1,2-c]quinazoline-7-carboxamide 
• 1256952-48-3 5-(furan-2-yl)-10-phenyl-8-(trifluoromethyl)-2,3-dihydroimidazo[1,2-c]quinazoline-7-carboxamide 
• 1256952-46-1 8-phenyl-5-(thiophen-2-yl)-10-(trifluoromethyl)-2,3-dihydroimidazo[1,2-c]quinazoline-7-carboxamide 
• 1256952-44-9 5-(4-hydroxyphenyl)-8-phenyl-10-(trifluoromethyl)-2,3-dihydroimidazo[1,2-c]quinazoline-7-carboxamide 
• 1256952-42-7 5-(furan-2-yl)-8-phenyl-10-(trifluoromethyl)-2,3-dihydroimidazo[1,2-c]quinazoline-7-carboxamide 
• 1256952-76-7 4-oxo-5-phenyl-2-(thiophen-2-yl)-7-(trifluoromethyl)-3,4-dihydroquinazoline-8-carboxamide 
• 1256952-74-5 2-(4-hydroxyphenyl)-4-oxo-5-phenyl-7-(trifluoromethyl)-3,4-dihydroquinazoline-8-carboxamide 
• 1256952-72-3 2-(furan-2-yl)-4-oxo-5-phenyl-7-(trifluoromethyl)-3,4-dihydroquinazoline-8-carboxamide 
• 1256952-70-1 4-oxo-7-phenyl-2-(thiophen-2-yl)-5-(trifluoromethyl)-3,4-dihydroquinazoline-8-carboxamide 
• 1256952-68-7 2-(4-hydroxyphenyl)-4-oxo-7-phenyl-5-(trifluoromethyl)-3,4-dihydroquinazoline-8-carboxamide 
• 1256952-66-5 2-(furan-2-yl)-4-oxo-7-phenyl-5-(trifluoromethyl)-3,4-dihydroquinazoline-8-carboxamide 

Relevant articles and documents

Synthesis, anti-inflammatory evaluation and docking studies of some new fluorinated fused quinazolines

A series of novel 8/10-trifluoromethyl-substituted-imidazo[1,2-c] quinazolines have been synthesized and evaluated in vivo (rat paw edema) for their anti-inflammatory activity and in silico (docking studies) to recognize the hypothetical binding motif of the title compounds with the cyclooxygenase isoenzymes (COX-1 and COX-2) employing GOLD (CCDC, 4.0.1 version) software. The compounds, 9b and 10b, were found to have good anti-inflammatory activity [around 80% of the standard: indomethacin]. The binding mode of the title compounds has been proposed based on the docking studies.

Synthesis and adenosine receptors binding studies of new fluorinated analogues of pyrido[2,3-d]pyrimidines and quinazolines

A series of new fluorine containing pyrido[2,3-d]pyrimidines and imidazo[1,2-c]pyrido[3,2-e]pyrimidines along with a series of bioisosteric fluorinated quinazolines were synthesised following appropriate synthetic schemes and characterised by spectral analytical means. X-ray crystal structure of the key precursor 1 (2-amino-3-cyano-4-trifluoro-methyl-6-phenyl-pyridine) was also determined to gain insight into its reactivity. Binding affinity data of all the compounds for adenosine receptors (ARs) showed that pyrido[2,3-d]pyrimidine scaffold with free amino (NH2) group at 2- and 4-position (2a) exhibited the maximum binding affinity for hA3 AR with similar affinity for the hA1 and somewhat lower affinity for hA2A ARs resulting in a compound with no A3 selectivity vs. A1 and moderate selectivity vs. A2A AR (Ki hA1 = 0.62 μM, hA2A = 3.59 μM and hA3 = 0.42 μM). Interestingly, the replacement of both the amino groups with carbonyl (C=O) groups (compound 4) resulted in significantly improved affinity for hA1 AR but with moderate selectivity against hA2A and hA3 ARs (Ki hA1 = 0.17 μM, hA2A = 0.67 μM and hA3 =0.68 μM). In case of fluorinated quinazolines, only compound 18a showed remarkable affinity for hA1 AR with significant selectivity against hA2A and hA3 ARs (Ki hA1 = 0.73 μM, hA2A CloseSPigtSPi 30 μM and hA3 = 9.27 μM). The preliminary results of these compounds demonstrate that the fluorinated pyrido[2,3-d]pyrimidine and imidazo[1,2-c]pyrido[3,2-e]pyrimidine can be considered as promising scaffolds for further optimisation in search of potential antagonists with better affinity and selectivity towards hA1 and hA3 ARs.

A simple and facile method for the synthesis of novel 5/7 triflouromethyl-substituted 4(3H)-quinazolone regioisomers

The unsymmetrical 1,3-diketones 1 on reaction with malononitrile is resulted an interesting trifunctional intermediates 2 and 3. The intermediate 2 is hydrolyzed to give 2,6-dicarboxamido aniline 4 which on cyclisation gave two regioisomers of 1,2-dihydro-4(3H)-quinazolinones 5 and 6. The effect of substituents on compound 4 is characteristic for formation of regioisomers in different proportions. Each regioisomer on dehydrogenation under mild condition using active MnO2 gave corresponding 4(3H)-quinazolones 7 and 8, respectively.

CYCLIZATION OF NITRILES. XVIII. SYNTHESIS AND SOME TRANSFORMATIONS OF 6-ARYL-4-TRIFLUOROMETHYL-3-CYANO-2(1H)-PYRIDINETHIONES

The reaction of 3-benzoyl- and 3-(2-thenoyl)-1,1,1-trifluoroacetone and also of 1-benzoyl- and 1-(2-thenoyl)-2-(1-morpholino)-3,3,3-trifluoro-1-propenes with cyanothioacetamide provides a convenient method for the production of 6-phenyl- and 6-(2-thienyl)-4-trifluoromethyl-3-cyano-2(1H)-pyridine thiones, which are used in the synthesis of substituted 3-aminothienopyridines and other condensed heterocyclic systems.