534-25-8

Basic information

• Product Name: 3H-1,2-DITHIOLE-3-THIONE
• Synonyms: 1,2-dithiol-3-thione;1,2-dithiole-3-thione;dithiole-3-thione
• CAS NO: 534-25-8
• Molecular Formula: C₃H₂S₃
• Molecular Weight: 134.24298
• EINECS: 208-595-0
• Product Categories: Heterocyclic Compounds;Heterocycles;Inhibitors;Sulfur & Selenium Compounds
• Mol File: 534-25-8.mol
• Article Data: 5

Chemical Properties

• Melting Point: 79-81°C
• Boiling Point: 235.5 °C at 760 mmHg
• Flash Point: 96.2 °C
• Appearance: /
• Density: 1.56g/cm³
• Vapor Pressure: 0.0763mmHg at 25°C
• Refractive Index: 1.806
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• CAS DataBase Reference: 3H-1,2-DITHIOLE-3-THIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3H-1,2-DITHIOLE-3-THIONE(534-25-8)
• EPA Substance Registry System: 3H-1,2-DITHIOLE-3-THIONE(534-25-8)

Safety Data

• Hazardous Substances Data: 534-25-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3H-1,2-Dithiole-3-thione is used as a chemoprotective agent for its ability to induce detoxication enzymes and inhibit chemical-induced tumors in multiple tissues. This application is particularly relevant in the development of cancer treatments, as it can help protect healthy cells from the harmful effects of chemotherapy while still targeting cancerous cells.
Used in Chemical Research:
Due to its unique chemical structure, 3H-1,2-Dithiole-3-thione can be utilized as a building block or intermediate in the synthesis of various organic compounds. It may be employed in the development of new drugs, materials, or other chemical products that require its specific properties.
Used in Material Science:
The red solid nature of 3H-1,2-Dithiole-3-thione suggests that it could potentially be used in the development of pigments or dyes for various applications, such as in the textile, paint, or plastics industries. Its unique structure may also contribute to the development of new materials with specific properties, such as improved conductivity or stability.

InChI:InChI=1/C3H2S3/c4-3-1-2-5-6-3/h1-2H

Upstream product

• 6028-61-1 dipropyl trisulfide 
• 75-15-0 carbon disulfide 
• 74-86-2 acetylene 
• 52687-98-6 1,4-di(n-propyl)tetrasulfane 
• 102-52-3 malonaldehydebis(dimethylacetal) 
• 187737-37-7 propene 

Relevant articles and documents

Synthesis of Dithiolethiones and Identification of Potential Neuroprotective Agents via Activation of Nrf2-Driven Antioxidant Enzymes

Oxidative stress is implicated in the pathogenesis of a wide variety of neurodegenerative disorders, and accordingly, dietary supplement of exogenous antioxidants or/and upregulation of the endogenous antioxidant defense system are promising for therapeutic intervention or chemoprevention of neurodegenerative diseases. Nrf2, a master regulator of the cellular antioxidant machinery, cardinally participates in the transcription of cytoprotective genes against oxidative/electrophilic stresses. Herein, we report the synthesis of 59 structurally diverse dithiolethiones and evaluation of their neuroprotection against 6-hydroxydopamine-or H2O2-induced oxidative damages in PC12 cells, a neuron-like rat pheochromocytoma cell line. Initial screening identified compounds 10 and 11 having low cytotoxicity but conferring remarkable protection on PC12 cells from oxidative-mediated damages. Further studies demonstrated that both compounds upregulated a battery of antioxidant genes as well as corresponding genes' products. Significantly, silence of Nrf2 expression abolishes cytoprotection of 10 and 11, indicating targeting Nrf2 activation is pivotal for their cellular functions. Taken together, the two lead compounds discovered here with potent neuroprotective functions against oxidative stress via Nrf2 activation merit further development as therapeutic or chemopreventive candidates for neurodegenerative disorders.

Convenient one-pot syntheses of 1,2-dithiole-3-thiones and 3-imino-1,2-dithioles from terminal alkynes

The reaction of acetylide anions with carbon disulfide or phenyl isothiocyanate followed by addition of sulfur in the presence of a protonating agent such as a primary amine or alcohol affords 1,2-dithiole-3-thiones or 3-imino-1,2-dithioles in good to excellent yields.

New ways of synthesis of 1,2-dithiole-3-thione

Two new synthetic approaches to 1,2-dithiole-3-thione are proposed. The title compound is formed by thermolysis of dipropyl polysulfides (n-Pr) 2Sx (x = 3-4) and thermal decomposition of polysulfide dendrimers under reduced pressure. The latter reaction may be recommended for utilization of organochlorine waste products in the manufacture of epichlorohydrin, which are used for the synthesis of dendrimers. 2004 MAIK "Nauka/Interperiodica".

N2S2 tetradentate ligands for soft cationic species: preparation of new ligands of potential interest in nuclear medicine

The synthesis of N2S2 tetradentate ligands of the bis-(enaminothioester) type was carried out starting from 3-(methylthio)-3H-1,2-dithiolylium iodides and diamines.The title compounds, which are potential ligands for soft cationic species, can be obtained from 1,3-diaminopropan-2-ol and subsequently modified into the dissymmetrical succinic acid ester of the ligand and N-hydroxysuccinimide.The appendage of such a linking group on the chelating structure should allow further grafting to monoclonal antibodies in view of potential applications in nuclear medicine. 3H-1,2-dithiole-3-thione / 1,3-diaminopropan-2-ol / bis-(enaminothioester) / N2S2 tetradentate ligand / N-hydroxysuccinimidyl ester

HIGH-TEMPERATURE ORGANIC SYNTHESIS XXXVIII. THERMAL SYNTHESIS OF 1,2-DITHIOLE-3-THIONES FROM POLYSULFIDES

The main product from the thermolysis of dipropyl polysulfides (C3H7)2Sn (n = 3-4) at 350-400 deg C is 1,2-dithiole-3-thione, and it is formed with yields of up to 52 percent. 4-Methyl-1,2-dithiole-3-thione was obtained from diisobutyl polysulfides (iso-C4H9)2Sn under analogous conditions with a yield of 68 percent.