2-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
CAS Number	137-07-5^Y
3D model (JSmol)	Interactive image
ChemSpider	21111815
ECHA InfoCard	100.004.798
EC Number	205-277-3
PubChem CID	8713
UNII	KIT82KOK2Z^Y
CompTox Dashboard (EPA)	DTXSID6051693
InChI 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
SMILES c1ccc(c(c1)N)S
Properties
Chemical formula	C6H7NS
Molar mass	125.19 g·mol^−1
Appearance	Colorless (impure samples are colored)
Density	1.200 g/cm^3
Melting point	26 °C (79 °F; 299 K)
Boiling point	234 °C (453 °F; 507 K)
Solubility in water	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 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 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