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

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

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

• 75-15-0 carbon disulfide 
• 273-77-8 benzo[1,2,3]thiadiazole 
• 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 
• 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 

Downstream Products

• 21870-33-7 5-(4-benzo[1,3]dithiol-2-ylidene-cyclohexa-2,5-dienylidene)-1,3-dimethyl-pyrimidine-2,4,6-trione 
• 274-30-6 1,3-benzodithiol 
• 57198-66-0 2,2'-sulfanediyl-bis-benzo[1,3]dithiole 
• 17534-15-5 Benzene-1,2-dithiol 
• 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 
• 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 

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.

Characterization of benzyl isothiocyanate extracted from mashed green papaya by distillation

The aim of this study was to extract benzyl isothiocyanate (BITC) from green papaya by distillation apparatus without using organic solvents, and to improve the stability of BITC in aqueous solution. The distillation of mashed green papaya successfully yielded BITC as a water solution with more than 80% purity with good reproducibility. The amount of BITC in the distilled water gradually decreased during its storage at 4 °C, whereas it was not significantly changed at ?20 °C for a few months. Moreover, the addition of L-cysteine ameliorated the BITC decomposition by the 4 °C-storage, but not affected by N-acetyl-cysteine and glutathione. These results suggested that the combination of BITC extraction by distillation and cysteine supplementation as well as frozen storage might be a useful method for the preparation and storage of the safer grade of BITC-containing extract.

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.

Comparison of bioactive phytochemical content and release of isothiocyanates in selected brassica sprouts

The consumption of brassica sprouts as raw vegetables provides a fair amount of glucosinolates (GLs) and active plant myrosinase, which enables the breakdown of GLs into health-promoting isothiocyanates (ITCs). This study reports the determination of the main constituents related to human health found in edible sprouts of two Brassica oleracea varieties, broccoli and Tuscan black kale, and two Raphanus sativus varieties, Daikon and Sango. Radish sprouts exhibited the highest ability to produce ITCs, with Daikon showing the greatest level of conversion of GLs into bioactive ITCs (96.5%), followed by Sango (90.0%). Tuscan black kale gave a value of 68.5%, whereas broccoli displayed the lowest with 18.7%. ITCs were not the exclusive GL breakdown products in the two B. oleracea varieties, since nitriles were also produced, thus accounting for the lower conversion observed. Measuring the release of plant ITCs is a valuable tool in predicting the potential level of exposure to these bioactive compounds after the consumption of raw brassica sprouts.

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.

ORGANIC SEMICONDUCTOR COMPOUND, SEMICONDUCTOR ELEMENT, SOLAR BATTERY, AND PROCESS FOR PRODUCING ORGANIC SEMICONDUCTOR COMPOUND

There is provided a compound or the like which can become a material in which many functions are controllable. A first aspect of the present invention lies in an organic semiconductor compound, characterized in that an organic molecule which becomes a donor is formed by being salt-formed with an inorganic acid or an inorganic base and self assembly is accomplished. According to this configuration, there can be obtained an organic semiconductor compound by a simple technique. A second aspect of the present invention lies in an organic compound, characterized in that a compound containing a tetrathiafulvalene affinity region in a framework thereof and having a protic acid functional group is formed by being induced to a salt with ammonia or a salt with hydroxyamine. According to this configuration, there can be obtained an organic compound in which many functions are controllable.

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.

New semiconducting benzo-TTF salts: Synthesis and physical properties

The synthesis of new π-electron donors of benzotetrathiafulvalene derivatives 4-11 with one or two hydroxyl functions and additional sulfur or selenium atoms is described. Their redox potentials were measured by cyclic voltammetry. Radical cation salts (RCS) and charge-transfer complexes (CTC) were prepared and their conductivities were measured. Some of the RCS are semi-conductors. Georg Thieme Verlag Stuttgart.

Synthesis of unsymmetrical tetrathiafulvalene derivatives via Me3Al-promoted reactions of organotin compounds with esters

Efficient synthetic methods for the construction of a wide variety of unsymmetrical tetrathiafulvalenes (TTFs) via the Me3Al-promoted reactions of organotin thiolates or selenolates with esters are described. Reaction of tin thiolates (3a-c and 10) and selenolates (3d, 5, and 7) with esters (11a,b) in the presence Of Me3Al as a Lewis acid gave dihydrotetrathiafulvalene derivatives (12, 14, 15, and 17-20) and 1,3-dithiane derivatives (13 and 16). In addition, the synthesis of diselenadithiafulvalene derivatives (25-28) could be accomplished by Me3Al-mediated reaction of tin thiolate (2a) or selenolates (3d and 5) with esters (22a, 22d, and 24). Furthermore, the application of the Me3Al-promoted reaction of tin thiolate (34) with esters (11a-b, 22a-d, and 35a-b) for the synthesis of unsymmetrical TTFs-fused donors enabled us to obtain various TTFs-fused systems (29-33) in short steps.

1,4-BENZODITHIIN 1,1,4,4,-TETRAOXIDE AS DIENOPHILE

1,4-Benzodithiin 1,1,4,4,-tetraoxide undergoes the Diels-Alder reaction with a series of dienes under mild condition to provide the corresponding adducts in excellent yields.The adduct with anthracene is desulfonated to afford dibenzobarrelene, thus showi