2-Aminothiophenol

2-Aminothiophenol is an organosulfur compound with the formula C6H4(SH)(NH2). 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
Names
Preferred IUPAC name
2-Aminobenzene-1-thiol
Other names
  • 2-Aminobenzenethiol
  • o-Amino-benzenethiol
  • 1-Amino-2-mercaptobenzene
  • 2-Amino-1-mercaptobenzene
  • 2-Mercaptoaniline
  • o-Aminobenzenethiol
  • o-Aminothiophenol
  • o-Mercaptoaniline
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.004.798
EC Number
  • 205-277-3
UNII
  • InChI=1S/C6H7NS/c7-5-3-1-2-4-6(5)8/h1-4,8H,7H2
    Key: VRVRGVPWCUEOGV-UHFFFAOYSA-N
  • InChI=1/C6H7NS/c7-5-3-1-2-4-6(5)8/h1-4,8H,7H2
    Key: VRVRGVPWCUEOGV-UHFFFAOYAG
  • c1ccc(c(c1)N)S
Properties
C6H7NS
Molar mass 125.19 g·mol−1
Appearance Colorless (impure samples are colored)
Density 1.200 g/cm3
Melting point 26 °C (79 °F; 299 K)
Boiling point 234 °C (453 °F; 507 K)
low
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

2-aminothiophenol can prepared in two steps, starting with the reaction of aniline with carbon disulfide followed by hydrolysis of the resulting mercaptobenzothiazole.[1] It can also obtained by zinc reduction of 2-nitrobenzenesulfonyl chloride.

References
  1. Chedekel, Miles R.; Sharp, Dale E.; Jeffery, Gary A. "Synthesis of o-Aminothiophenols" Synthetic Communications 1980, volume 10, pp. 167-73. doi:10.1080/00397918008064218
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