2-Indolinethione

2-Indolinethione

Names
Other names 1,3-Dihydroindole-2-thione
Identifiers
CAS Number	496-30-0  Y 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
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: [1]
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

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.