phenetidine

Phenetidine refers to a group of organic compounds with the chemical formula C8H11NO. Specifically, it is an aniline derivative where an ethoxy group (-OCH2CH3) is attached to the benzene ring. The most common isomers are para-phenetidine (4-ethoxyaniline) and ortho-phenetidine (2-ethoxyaniline), with meta-phenetidine (3-ethoxyaniline) also existing.

Para-phenetidine is a colorless to yellowish liquid with a characteristic odor. It is sparingly soluble in water but soluble in organic solvents. It finds applications as an intermediate in the synthesis of dyes and pharmaceuticals. For example, it is a precursor to phenacetin, a once-popular analgesic and antipyretic drug, although phenacetin has largely been withdrawn from the market due to potential kidney toxicity.

Ortho-phenetidine is also a liquid with similar solubility properties. It is used in the production of certain azo dyes and as a chemical reagent.

The synthesis of phenetidines typically involves the ethoxylation of aniline or the reduction of the corresponding nitrophenetole. Due to their aniline structure, phenetidines can exhibit toxic properties and should be handled with care, avoiding skin contact and inhalation.