13232-76-3

Basic information

• Product Name: 4,5-Diphenyl-3H-1,2-dithiole-3-thione
• Synonyms: 4,5-Diphenyl-3H-1,2-dithiole-3-thione
• CAS NO: 13232-76-3
• Molecular Formula: C₁₅H₁₀S₃
• Molecular Weight: 286.43
• Mol File: 13232-76-3.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 457.7°C at 760 mmHg
• Flash Point: 230.6°C
• Appearance: /
• Density: 1.38g/cm³
• Vapor Pressure: 3.98E-08mmHg at 25°C
• Refractive Index: 1.768
• CAS DataBase Reference: 4,5-Diphenyl-3H-1,2-dithiole-3-thione(CAS DataBase Reference)
• NIST Chemistry Reference: 4,5-Diphenyl-3H-1,2-dithiole-3-thione(13232-76-3)
• EPA Substance Registry System: 4,5-Diphenyl-3H-1,2-dithiole-3-thione(13232-76-3)

Safety Data

• Hazardous Substances Data: 13232-76-3(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 95, p. 5781, 1973 DOI: 10.1021/ja00798a068

InChI:InChI=1/C15H10S3/c16-15-13(11-7-3-1-4-8-11)14(17-18-15)12-9-5-2-6-10-12/h1-10H

Upstream product

• 670-80-4 4-cyclohexen-1-ylmorpholine 
• 80158-70-9 4,5-Diphenyl-3H-1,2-dithiol-3-thion-S-oxid 
• 19018-13-4 2-[4-(2-Oxo-1,2-diphenyl-ethylidene)-[1,3]dithietan-2-ylidene]-1,2-diphenyl-ethanone 
• 17835-44-8 4,5-diphenyl-3H-1,2-dithiol-3-one 
• 2570-01-6 2,3-diphenylcyclopropen-1-thione 
• 886-38-4 diphenylcyclopropenone 
• 65-85-0 benzoic acid 
• 103-82-2 phenylacetic acid 
• 98-88-4 benzoyl chloride 
• 101-97-3 Ethyl 2-phenylethanoate 
• 58929-02-5 ethyl 2,3-diphenyl-3-oxopropanoate 
• 70671-91-9 3-bromo-1,2-diphenyl-propene 
• 5342-87-0 1,2-diphenylpropane-2-ol 
• 532-11-6 anethole trithione 

Downstream Products

• 13232-77-4 3-(Methylthio)-4,5-diphenyl-1,2-dithiolium-iodid 
• 1820-42-4 bis(4-chlorophenyl)acetylene 
• 81385-73-1 5,6-Bis(4-chlorphenyl)-2,3-diphenylthieno<3,2-b>furan 
• 81385-75-3 5,6-Bis-(4-chloro-phenyl)-2-[1,2-diphenyl-2-thioxo-eth-(E)-ylidene]-[1,3]dithiin-4-one 
• 81385-74-2 5,6-Bis-(4-chloro-phenyl)-2-[1,2-diphenyl-2-thioxo-eth-(Z)-ylidene]-[1,3]dithiin-4-one 
• 81385-76-4 4,5-bis(4-methoxyphenyl)-3H-1,2-dithiol-3-one 
• 81385-77-5 5,6-Bis(4-methoxyphenyl)-2,3-diphenylthieno<3,2-b>furan 
• 77654-98-9 (diethylamino-4 methyl-5 dithiole-1,3 ylidene-2)-2 diphenyl-1,2 ethanethione 
• 17835-44-8 4,5-diphenyl-3H-1,2-dithiol-3-one 
• 80608-91-9 2,3,5,6-Tetraphenylthieno<3,2-b>furan 
• 81385-51-5 2-[1,2-Diphenyl-2-thioxo-eth-(Z)-ylidene]-5,6-diphenyl-[1,3]dithiin-4-one 
• 81385-79-7 5-Methyl-2,3,6-triphenylthieno<3,2-b>furan 
• 35093-32-4 2,3,5,6-tetraphenylthieno[3,2-b]thiophene 
• 80158-70-9 4,5-Diphenyl-3H-1,2-dithiol-3-thion-S-oxid 

Relevant articles and documents

Synthesis, characterization, and oxidation electrochemistry of some novel 1,2-dithiol-3-ones and 1,2-dithiol-3-thiones containing aryl and metallocenyl fragments

A new synthesis method was established for 1,2-dithiol-3-ones and 1,2-dithiol-3-thiones, from different cyclopropenones: diphenyl (a), bis-(4-methoxyphenyl (b), diferrocenyl (c) and diruthenocenyl (d), in the presence of elemental sulfur with yields of the 5a-d (35–57%), or in the presence of the additive NaHS, with yields of the 5a-d (45–72%) and 6a-d (10–18%). The characterization of the new compounds was conducted by IR, 1H and 13C NMR spectroscopy, elemental analysis, mass-spectrometry. In addition, X-ray crystallographic analysis of the compounds 5a,b,d was conducted. The redox properties of the heterocyclic compounds were investigated using cyclic (CV), differential pulse (DPV) and square wave (SWV) voltammetries.

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.

THERMOLYSIS OF 1,3-DITHIOL-2-YL AZIDES AND THERMAL PROPERTIES OF THE RESULTING 1,4,2-DITHIAZINES

2-Substituted 1,3-dithiol-2-yl azides, on thermolysis in refluxing toluene, give 3-substituted 1,4,2-dithiazines wich thermally extrude sulfur atom of the 4-position selectively to yield 3-substituted isothiazoles, while 2-unsubstituted 1,3-dithiol-2-yl azides undergo both ring expansion yielding 1,4,2-dithiazines and peculiar thermal dissociation into 1,3-dithiol-2-ylidene carbenes and hydrogen azide.