1,2-Dithiole

Base Information

• Chemical Name: 1,2-Dithiole
• CAS No.: 288-26-6
• Molecular Formula: C3H4 S2
• Molecular Weight: 104.19
• DSSTox Substance ID: DTXSID901031881
• Nikkaji Number: J921.755J
• Wikipedia: 1,2-Dithiole
• Wikidata: Q18343387
• Mol file: 288-26-6.mol

Synonyms:1,2-dithiole;3H-1,2-Dithiole;3H-1,2-dithiolene;1,2-Dithiolene;3H-1,2-Dithiol;1,2-Dithiacyclopentene;SCHEMBL22568;DTXSID901031881;Q18343387;Ref.: J.Agric. Food Chem., Vol. 46, #1, 1998, 220-223;1,3-Dibicyclo[2.2.1]hepta-2,5-dien-2-yl-1,3-dichloro-1,3-bis[3-(trimethylsilyl)propyl]disiloxane;288-26-6

Chemical Property of 1,2-Dithiole

Chemical Property:

• Boiling Point: 146.5±23.0 °C(Predicted)
• Density: 1.286±0.06 g/cm3(Predicted)
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 103.97544247
• Heavy Atom Count: 5
• Complexity: 48.9

Purity/Quality:

99% ^*data from raw suppliers

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• Canonical SMILES: C1C=CSS1

Refernces

Regioselective synthesis of 1,3-thiazines by sequential 4-oxothiazolidine to 1,2-dithiole to 1,3-thiazine transformations: role of intramolecular non-bonded S?O interactions

10.1016/j.tet.2006.12.075

The study presents a novel synthetic approach to 2,3-dihydro-4H-1,3-thiazine derivatives, which involves the reductive rearrangement of 1,2-dithiole-3ylidene thiones. The process begins with the preparation of 1,2-dithiole derivatives from 2-alkylidene-4-oxothiazolidines, which are induced by intramolecular non-bonded 1,5-type S/O interactions in the presence of Lawesson’s reagent (LR). The chemicals used in the study include 2-alkylidene-4-oxothiazolidines, LR for inducing the ring-opening-closing process, and sodium borohydride for the reductive rearrangement step. These chemicals serve the purpose of transforming the initial compounds into functionalized 1,2-dithiole-3-ylidene thiones and subsequently into 2,3-dihydro-4H-1,3-thiazine-4-thiones, demonstrating the ease of interconversion between three structurally different heterocyclic classes via two efficient sequential transformations. The study also includes X-ray crystallography to confirm the structures of the synthesized compounds.

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