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Medicinal chemistry and drug research require diverse chemical components to meet strict requirements not only in terms of physical and chemical properties but also in terms of chemical reactivity.
The chemists use the 'build–couple–pair' strategy of organic synthesis, which entails preparing molecular building blocks that contain several chemical groups.
The chemical building block (CBB) is a molecule which can be converted to various secondary chemicals and intermediates, and, in turn, into a broad range of different downstream uses.
Amine is a class of organic compound containing at least one N atom. In other words, amine can be regarded as substituted product of ammonia gas in which one or multiple hydrogen atoms are replaced by hydrocarbons. Based on the types of hydroxyl groups attached to N atoms, amine can be divided into fatty amines and aromatic amines. Lower fatty amines possess large solubility which can be attributed to the formation of hydrogen bond between amine molecule and water. Similar to ammonia, amine show alkalinity due to the unshared pairs of electrons of N atom.
As one of the most important amines, anilines have attracted numerous attention and found various application in practical utilization. Anilines also show weak alkalinity due to conjugation of N with aromatic ring, which makes it capable of precipitating trivalent or quadrivalent metal ion and separating them out. In addition, anilines can occur a variety of reactions involved substitution reaction, acetylation and halogenation. It is worthy noting that aniline is very toxic to blood and nerves and could cause poisoning through skin absorrtion and respiratory suction.
There are two main approach to produce aniline:
Anilines are a class of important raw materials for the production of pesticides. Anilines derivatives including N-alkyl aniline, adjacent nitro aniline and phenylhydrazine play a significant role in sterilization. And many of the anilines derivatives are important reaction intermidiates when preparing common bactericide, insecticide and herbicide.
Some anions such as thiocyanate complex anions can be detected by anilines because anilines can react with them and precipitate would be formed. In addition, nitrite and carboxylic acid can also be examined by anilines.
As one of the most important intermediates in the dye industry, anilines an be used to produce a variety of dye including indigo, acid media BS and direct pink. Anilines derivatives with different substitute effect can be found in the preparation of many coomon dye.
(Chem. Commun. ,2006(21), 2245)
(OrgLett. ,2008, 11(1), 97)
Owing the presence of active –NH2 group, the hydrogen atom can be replaced by alkyl or acyl groups to secondary or tertiary anilines and acylanilines. Aromatic ring structure of anilines also makes them a useful candidate for the construction of organic compounds.