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 ;
3D model (JSmol)	Interactive image;
ChemSpider	21111815;
ECHA InfoCard	100.004.798
EC Number	205-277-3;
PubChem CID	8713;
UNII	KIT82KOK2Z ;
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/cm3
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.

Applications

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

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

References

^ 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

[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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