Zhang, Chen;Zhuang, Dao-Min;Li, Jia;Chen, Si-Yuan;Du, Xiao-Long;Wang, Jian-Yong;Li, Jing-Yun;Jiang, Biao;Yao, Jian-Hua published 《Diverse reactivity in microwave-promoted catalyst-free coupling of substituted anilines with ethyl trifluoropyruvate and biological evaluation》. The research results were published in《Organic & Biomolecular Chemistry》 in 2013.Quality Control of 3-(4-Aminophenoxy)aniline The article conveys some information:
Diverse reactivity by coupling of substituted anilines with Et trifluoropyruvate was developed under microwave irradiation without catalysts to generate 3-trifluoromethyl-3-hydroxyoxindoles, aromatic hydroxy trifluoromethyl esters, and 1,2-dicarbonyl compounds in a fast and efficient manner. The plausible mechanism for obtaining different products was proposed. Furthermore, the anti-HIV activity of aromatic hydroxy trifluoromethyl esters was first reported. The best inhibitory activity against wild-type HIV-1 IIIB was exemplified by trifluoromethyloxindole I with an IC50 = 5.8 μM, which also displayed potential activity against Y181C mutant virus with an IC50 = 7.5 μM. More significantly, the activities of oxindoles I and II to inhibit K103N/Y181C double mutant HIV-1 reverse transcriptase (RT) are probably similar to that of the second-generation nonnucleoside inhibitor HBY 097 by docking calculation To complete the study, the researchers used 3-(4-Aminophenoxy)aniline (cas: 2657-87-6) .
3-(4-Aminophenoxy)aniline is one of ethers-buliding-blocks. Ethers lack the hydroxyl groups of alcohols. Without the strongly polarized O―H bond, ether molecules cannot engage in hydrogen bonding with each other. Quality Control of 3-(4-Aminophenoxy)anilineEthers do have nonbonding electron pairs on their oxygen atoms, however, and they can form hydrogen bonds with other molecules (alcohols, amines, etc.) that have O―H or N―H bonds.
Reference:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem