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2-Aminothiophenol

2-Aminothiophenol is an organosulfur compound with the formula C<sub>6</sub>H<sub>4</sub>(SH)(NH<sub>2</sub>). It is a colorless oily solid, although impure samples can be deeply colored. It is soluble in organic solvents and in basic water. 2-Aminothiophenol is a precursor to benzothiazoles, some of which are bioactive or are commercial dyes. Isomers of aminothiophenols include 3-aminothiophenol and 4-aminothiophenol.

2-Aminothiophenol can prepared in two steps, starting with the reaction of aniline with carbon disulfide followed by hydrolysis of the resulting mercaptobenzothiazole. It can also obtained by zinc reduction of 2-nitrobenzenesulfonyl chloride.

Applications

2-Aminothiophenol is used in the synthesis of the following list of agents:

  1. DDD-016
  2. BTM 1086
  3. Thioproperazine
  4. Cinanserin
  5. 1-Azaphenothiazine [261-96-1] (finds use in synthesis of Pipazethate, Prothipendyl, Cloxypendyl, Oxypendyl, & Isothipendyl).

References