499-08-1

Usage

Chemical Properties

Pale yellow crystals

InChI:InChI=1/C7H6FNO2/c1-5-2-6(8)4-7(3-5)9(10)11/h2-4H,1H3

Upstream product

• 618-85-9 3,5-dinitrotoluene 
• 618-61-1 3-methyl-5-nitro-aniline 

Downstream Products

• 35113-97-4 3-methoxy-5-methyl-nitrobenzene 
• 1442474-02-3 1-(4-chloro-5-(1-ethyl-7-(methylamino)-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-2-fluorophenyl)-3-(3-fluoro-5-((4-methylpiperazin-1-yl)methyl)phenyl)urea 
• 1442474-01-2 3-fluoro-5-((4-methylpiperazin-1-yl)methyl)aniline 
• 1442474-00-1 1-(3-fluoro-5-nitrobenzyl)-4-methylpiperazine 
• 883987-75-5 1-(bromomethyl)-3-fluoro-5-nitrobenzene 
• 135340-66-8 5-Amino-1-[3-chloro-4-(4-chloro-benzoyl)-5-fluoro-benzyl]-1H-[1,2,3]triazole-4-carboxylic acid amide 
• 135340-50-0 (4-Bromomethyl-2-chloro-6-fluoro-phenyl)-(4-chloro-phenyl)-methanone 
• 135340-38-4 2',4''-dichloro-6'-fluoro-4'-methylbenzophenone 
• 93857-90-0 1-chloro-3-fluoro-5-methylbenzene 
• 66584-31-4 3-methoxy-5-methylphenylamine 
• 52215-41-5 3-fluoro-5-methylaniline 

Relevant academic research and scientific papers

Benzylated 1,2,3-triazoles as anticoccidiostats

Substituted 5-amino-4-carbamoyl-1,2,3-triazoles 3a-w were prepared by two synthetic schemes and evaluated in vivo for anticoccidial activity. Both schemes proceeded by brominating appropriately substituted toluenes 4a-s,v to 5a-s,v. In Scheme I, the brominated benzyl analogues 5 were converted to the corresponding benzyl azides 6, which were treated with cyanoacetamide to yield 1-substituted-5-amino-4-carbamoyl-1,2,3-triazoles 3. In Scheme II, the benzyl halides 5 were employed to alkylate the sodium salt of 5-amino-4-carbamoyl-1,2,3-triazole (7). Preliminary screening data against Eimeria acervulina and E. tenella in chickens suggested structural requirements for maximizing activity. Further evaluation against a relatively resistant series of eight Eimeria field isolates revealed L-651,582 (3a) to be a highly effective coccidiostat. However, unacceptable tissue residues precluded further development. Mechanistic studies on this series of 5-amino-4-carbamoyl-1,2,3-triazoles and, in particular, on L-651,582 (3a) revealed that its mode of action does not involve inhibition of IMP dehydrogenase, but probably interferes with host cell calcium entry. In addition, L-651,582 has been found to have antiproliferative activity in several disease models and was recently reported to possess antimetastatic activity in a model of ovarian cancer progression.

The Kinetics of the Reactions of Picryl Chloride with Some Substituted Anilines. Part 5.

Arrhenius parameters have been measured for the reactions of picryl chloride with the following substituted anilines in acetonitrile: 3-amino- and 3-methyl-aniline, 3-amino-5-nitroaniline, 3-fluoro-5-methylsulphonylaniline, 3-X-5-methylanilines (X=NO2, OMe, CH3, F, Cl, Br, or I) and 3,5-X2-anilines (X = F, Cl, Br, or I).A total of 33 3,5-disubstituted anilines have now been examined for the additivity of substituent effects on the free energy of activation, and it has been shown that with the exception of 3-amino-5-nitroaniline this hypothesis reproduces experimental rate constants within a factor of 2.A rationalization is proposed for the deviations that occur in some cases when more stringent criteria of additivity are used.