934-36-1

Basic information

• Product Name: 1,3-benzodithiole-2-thione
• Synonyms: 1,3-benzodithiole-2-thione;2H-1,3-benzodithiole-2-thione
• CAS NO: 934-36-1
• Molecular Formula: C₇H₄S₃
• Molecular Weight: 184.3017
• Mol File: 934-36-1.mol
• Article Data: 18

Chemical Properties

• Boiling Point: 338.6°C at 760 mmHg
• Flash Point: 158.6°C
• Density: 1.52g/cm³
• Vapor Pressure: 0.000191mmHg at 25°C
• Refractive Index: 1.819
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility: DMSO (Slightly, Sonicated), Methanol (Slightly, Sonicated)
• CAS DataBase Reference: 1,3-benzodithiole-2-thione(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-benzodithiole-2-thione(934-36-1)
• EPA Substance Registry System: 1,3-benzodithiole-2-thione(934-36-1)

Safety Data

• Hazardous Substances Data: 934-36-1(Hazardous Substances Data)

Usage

Description

1,3-Benzodithiole-2-thione, also known as 2H-1,3-benzodithiole-2-thione, is an organic compound belonging to the class of isothiocyanates. It is characterized by the presence of a benzene ring with two sulfur atoms and a thiol group attached to the thiophene ring. This unique structure endows it with various biological activities and potential applications in different fields.

Uses

Used in Pharmaceutical Industry:
1,3-Benzodithiole-2-thione is used as a dietary isothiocyanate for the suppression of prostate carcinogenesis. Its chemopreventive properties are attributed to its ability to modulate various cellular signaling pathways, leading to the inhibition of cancer cell growth and proliferation. It also exhibits anti-inflammatory and antioxidant effects, which contribute to its potential as a therapeutic agent in cancer prevention and treatment.
In addition to its application in prostate cancer prevention, 1,3-Benzodithiole-2-thione may also have potential uses in other industries, such as:
Used in Cosmetic Industry:
1,3-Benzodithiole-2-thione can be used as an active ingredient in cosmetic products for its antioxidant and anti-inflammatory properties. It may help protect the skin from environmental stressors and promote skin health by reducing inflammation and oxidative stress.
Used in Agricultural Industry:
As a dietary isothiocyanate, 1,3-Benzodithiole-2-thione may also have potential applications in agriculture as a natural pesticide or fungicide. Its antimicrobial and antifungal properties could be utilized to protect crops from various pathogens and pests, promoting sustainable agriculture practices.

Synthesis Reference(s)

Tetrahedron Letters, 25, p. 833, 1984 DOI: 10.1016/S0040-4039(01)80039-3

Upstream product

• 622-78-6 Benzyl isothiocyanate 
• 17534-15-5 Benzene-1,2-dithiol 
• 75-15-0 carbon disulfide 
• 6461-76-3 1,2-benzenedisulfonyl dichloride 
• 137-07-5 2-amino-benzenethiol 
• 274-30-6 1,3-benzodithiol 
• 463-71-8 thiophosgene 
• 822-38-8 1,3-dithiolane-2-thione 
• 4661-46-5 2-carboxybenzene diazonium chloride 
• 542-85-8 Ethyl isothiocyanate 
• 80541-37-3 3-Benzo[1,3]dithiol-2-ylidene-benzo[1,4]dithiine-2-thione 
• 108-98-5 thiophenol 
• 57842-27-0 1,3-benzodithiol-2-ylium tetrafluoroborate 
• 2388-68-3 o-bis(mercaptomethyl)benzene 

Downstream Products

• 1215267-01-8 C₁₉H₁₃NO₂S₅ 
• 87543-10-0 <4,4-(1,2-Benzenediyldithio)but-3-enyl>benzene 
• 36198-83-1 2-({2-[(2-hydroxy-2-oxoethyl)thio]phenyl}thio)acetic acid 
• 274-30-6 1,3-benzodithiol 
• 17534-15-5 Benzene-1,2-dithiol 
• 57198-66-0 2,2'-sulfanediyl-bis-benzo[1,3]dithiole 
• 90703-72-3 2-methyl-2-(methylthio)-1,3-benzo-dithiolate 
• 24648-13-3 dibenzotetrathiafulvalene 
• 120120-58-3 bis(ethylenedioxy)tetrathiafulvalene 
• 131158-19-5 Ethylenedioxybenzotetrathiafulvalene 
• 129225-89-4 2-(3-m-methoxyphenylpropyl)-2-methylthio-1,3-benzodithiole 
• 129225-90-7 2-methylthio-2-(3-phenylpropyl)-1,3-benzodithiole 
• 21870-33-7 5-(4-benzo[1,3]dithiol-2-ylidene-cyclohexa-2,5-dienylidene)-1,3-dimethyl-pyrimidine-2,4,6-trione 

Relevant articles and documents

Reactions of Benzyne with 1,3-Benzodithiole-2-thione and Related Compounds: Formation of Novel Tetracyclic Sulfonium Salts and Their Reactions Leading to Dibenzo-1,3,6,-trithiocin Derivatives

A sulfur ylide intermediate, produced by a 1,3-dipolar cycloaddition of 1,3-benzodithiole-2-thione (5) with benzyne, was successfully trapped by hydrogen chloride to give a novel tetracyclic sulfonium salt, 9aH-9,10-dithia-4b-thioniaindeno[1,2-a]indene chloride (7), in good yield when benzyne was generated by the thermolysis of 2-carboxybenzenediazonium chloride (4). The reaction of ethylene trithiocarbonate with excess 4 provided a convenient one-pot synthesis of 7 in large quantities. The reduction of 7 with NaBH4 gave a novel ring compound, dibenzo[d,g][1,3,6]trithiocin (15), in 95% yield, while alkaline hydrolysis produced the 12-oxide derivative of 15. The treatment of 7 with t-BuOK gave 6,6′-bi(dibenzo[d,g][1,3,6]trithiocinylidene) in 84% yield. Also described are the reactions of benzyne with related compounds of 5.

Reactions of 1,3-benzodithiole-2-thione and ethylene trithiocarbonate with benzyne generated from 2-carboxybenzenediazonium chloride: Preparation of novel bicyclic sulfonium salts by trapping 1,3-dipolar cycloaddition intermediates

The reaction of benzyne, generated from 2-carboxybenzenediazonium chloride 4, with 1,3-benzodithiole-2-thione gives the novel bicyclic sulfonium chloride 7 by trapping of the 1,3-dipolar cycloaddition intermediate 6 with hydrogen chloride which when treated with ethylene trithiocarbonate affords 7 in one-pot in good yields.

Synthesis and complexation study of new ExTTF-based hosts for fullerenes

A new series of exTTF hosts has been synthesized for supramolecular binding study of fullerenes C60 and C70. Binding constants for C60 in chlorobenzene, toluene, toluene-CH2Cl2 and CS2 have been calculated for different hosts and a direct structure-affinity relationship has been established. As predicted, receptors with two exTTF moieties (1, 3 and 4) have demonstrated higher binding abilities toward C70 than C60. Depending on the linker used to attach the exTTF unit to the core of the host, different binding modes (1:1 and 2:1) have been obtained. This journal is the Partner Organisations 2014.

Electrochemical transformation of diazonium salts into diaryl disulfides

Electrolyses of aryldiazonium tetrafluoroborates in CS2/EtOH and Bu4NClO4, as the solvent-supporting electrolyte system, led to the corresponding diaryl disulfides in good yields.