《C-H chlorination of (hetero)anilines via photo/organo co-catalysis》 was published in Organic & Biomolecular Chemistry in 2022. These research results belong to Xie, Wuchen; Wang, Meng; Yang, Siyu; Chen, Yadong; Feng, Jie; Huang, Yatian. Reference of 2-Amino-3-Bromo-5-chlorobenzonitrile The article mentions the following:
Herein, a photo-redox and organo co-catalyzed chlorination method for anilines to gave chloro-anilines ArNR1R2 [Ar = 4-ClC6H4, 3,4-di-Cl-5-FC6H2, 4-Cl-2,5-di-FC6H2, etc.; R1 = H, Me; R2 = H, Me, C(O)Me, Ph, pyrimidin-2-yl; R1R2 = (CH2)2N(CH3)(CH2)2] was disclose. This method had great substrate generality and excellent mono-chlorination selectivity. Another merit of this method was the late-stage modification of drug mols., which would be useful in medicinal chem.2-Amino-3-Bromo-5-chlorobenzonitrile(cas: 914636-84-3Reference of 2-Amino-3-Bromo-5-chlorobenzonitrile) was used in this study.
2-Amino-3-Bromo-5-chlorobenzonitrile(cas: 914636-84-3) belongs to anime. Nitrous acid converts secondary amines (aliphatic or aromatic) to N-nitroso compounds (nitrosamines): R2NH + HNO2 → R2N―NO. Some nitrosamines are potent cancer-inducing substances, and their possible formation is a serious consideration when nitrites, which are salts of nitrous acid, are present in foods or pharmaceutical preparations. Tertiary amines give rise to nitrosamines more slowly; an alkyl group is eliminated as an aldehyde or ketone, along with nitrous oxide, N2O.Reference of 2-Amino-3-Bromo-5-chlorobenzonitrile
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts