2-Indolinethione

2-Indolinethione
Names
	Preferred IUPAC name 1,3-Dihydro-2H-indole-2-thione
	Other names 1,3-Dihydroindole-2-thione
Identifiers
CAS Number	496-30-0 ; tautomer: 53497-58-8;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL1345979;
ChemSpider	2297319; tautomer: 11341121;
ECHA InfoCard	100.220.246
EC Number	692-228-8;
PubChem CID	3032310;
UNII	S9SC88MKF6 ;
CompTox Dashboard (EPA)	DTXSID20197921 ;
	InChI InChI=1S/C8H7NS/c10-8-5-6-3-1-2-4-7(6)9-8/h1-4H,5H2,(H,9,10) Key: IGJWTYFTQNHSEK-UHFFFAOYSA-N;
	SMILES C1C2=CC=CC=C2NC1=S;
Properties
Chemical formula	C8H7NS
Molar mass	149.21 g·mol−1
Appearance	white solid
Density	1.27 g/cm3
Melting point	44–45 °C (111–113 °F; 317–318 K)
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302, H315, H319, H335
Precautionary statements	P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

2-Indolinethione is an organic compound with the formula C₈H₆(S)(NH). It is a derivative of dihydroindole containing a thione group. The compound is a tautomer of 2-mercaptoindole. A white solid, it is prepared by thiation of 2-oxindole.^[2]^[3] 2-Indolinethione is a precursor to several natural products.^[4]

References

↑ "2-Indolinethione". pubchem.ncbi.nlm.nih.gov.
↑ Hino, Tohru; Tsuneoka, Kazuko; Nakagawa, Masako; Akaboshi, Sanya (1969). "Thiation of Oxindoles". Chemical and Pharmaceutical Bulletin. 17 (3): 550–558. doi:10.1248/cpb.17.550.
↑ Bergman, Jan; Pettersson, Birgitta; Hasimbegovic, Vedran; Svensson, Per H. (2011). "Thionations Using a P₄S₁₀−Pyridine Complex in Solvents Such as Acetonitrile and Dimethyl Sulfone". The Journal of Organic Chemistry. 76 (6): 1546–1553. doi:10.1021/jo101865y. PMID 21341727.
↑ Pedras, M. Soledade C.; Jha, Mukund (2005). "Concise Syntheses of the Cruciferous Phytoalexins Brassilexin, Sinalexin, Wasalexins, and Analogues: Expanding the Scope of the Vilsmeier Formylation". The Journal of Organic Chemistry. 70 (5): 1828–1834. doi:10.1021/jo0479866. PMID 15730307.

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[1] "2-Indolinethione". pubchem.ncbi.nlm.nih.gov.

[2] Hino, Tohru; Tsuneoka, Kazuko; Nakagawa, Masako; Akaboshi, Sanya (1969). "Thiation of Oxindoles". Chemical and Pharmaceutical Bulletin. 17 (3): 550–558. doi:10.1248/cpb.17.550.

[3] Bergman, Jan; Pettersson, Birgitta; Hasimbegovic, Vedran; Svensson, Per H. (2011). "Thionations Using a P₄S₁₀−Pyridine Complex in Solvents Such as Acetonitrile and Dimethyl Sulfone". The Journal of Organic Chemistry. 76 (6): 1546–1553. doi:10.1021/jo101865y. PMID 21341727.

[4] Pedras, M. Soledade C.; Jha, Mukund (2005). "Concise Syntheses of the Cruciferous Phytoalexins Brassilexin, Sinalexin, Wasalexins, and Analogues: Expanding the Scope of the Vilsmeier Formylation". The Journal of Organic Chemistry. 70 (5): 1828–1834. doi:10.1021/jo0479866. PMID 15730307.

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References