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

Uses

2H-1,3-benzodithiole-2-thione is a dietary isothiocyanate that is used in the suppression of prostate carcinogenesis.

Synthesis Reference(s)

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

Upstream product

• 75-15-0 carbon disulfide 
• 273-77-8 benzo[1,2,3]thiadiazole 
• 822-38-8 1,3-dithiolane-2-thione 
• 4661-46-5 2-carboxybenzene diazonium chloride 
• 622-78-6 Benzyl isothiocyanate 
• 17534-15-5 Benzene-1,2-dithiol 
• 556-61-6 methyl thioisocyanate 
• 118-92-3 anthranilic acid 
• 6461-76-3 1,2-benzenedisulfonyl dichloride 
• 137-07-5 2-amino-benzenethiol 
• 274-30-6 1,3-benzodithiol 
• 463-71-8 thiophosgene 
• 542-85-8 Ethyl isothiocyanate 
• 80541-37-3 3-Benzo[1,3]dithiol-2-ylidene-benzo[1,4]dithiine-2-thione 

Downstream Products

• 274-30-6 1,3-benzodithiol 
• 17534-15-5 Benzene-1,2-dithiol 
• 1215267-01-8 C₁₉H₁₃NO₂S₅ 
• 87543-10-0 <4,4-(1,2-Benzenediyldithio)but-3-enyl>benzene 
• 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 
• 36198-83-1 2-({2-[(2-hydroxy-2-oxoethyl)thio]phenyl}thio)acetic acid 

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.