49638-64-4

Basic information

• Product Name: 4,5-BIS(METHYLTHIO)-1,3-DITHIOLE-2-THIONE
• Synonyms: RARECHEM AR PA 0057;4,5-BIS(METHYLTHIO)-1,3-DITHIOLE-2-THIONE;4,5-BIS(METHYLTHIO)-1,3-DITHIOL-2-THIONE;4,5-Bis(methylthio)-2H-1,3-dithiole-2-thione ;Bismethylthiodithiolethione;1,3-Dithiole-2-thione, 4,5-bis(methylthio)-;4,5-BIS(METHYLTHIO)-1,3-DITHIOLE-2-THIONE 98+%;4,5-BIS(METHYLTHIO)-1,3-DITHIOLE-2-THIONE 97%
• CAS NO: 49638-64-4
• Molecular Formula: C₅H₆S₅
• Molecular Weight: 226.43
• Product Categories: Sulphur Derivatives;Heterocyclic Compounds;Charge Transfer Complexes (Synthetic Intermediates);Charge Transfer Complexes for Organic Metals;Functional Materials
• Mol File: 49638-64-4.mol
• Article Data: 2

Chemical Properties

• Melting Point: 102 °C
• Boiling Point: 312.4°C at 760 mmHg
• Flash Point: 142.7°C
• Appearance: /
• Density: 1.53g/cm³
• Vapor Pressure: 0.000975mmHg at 25°C
• Refractive Index: 1.778
• Solubility: within almost transparency in hot EtOH
• CAS DataBase Reference: 4,5-BIS(METHYLTHIO)-1,3-DITHIOLE-2-THIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4,5-BIS(METHYLTHIO)-1,3-DITHIOLE-2-THIONE(49638-64-4)
• EPA Substance Registry System: 4,5-BIS(METHYLTHIO)-1,3-DITHIOLE-2-THIONE(49638-64-4)

Safety Data

• Hazardous Substances Data: 49638-64-4(Hazardous Substances Data)

Usage

General Description

4,5-Bis(methylthio)-1,3-dithiole-2-thione, also known as 4,5-bis(methylthio)-1,3-dithiol-2-one, is a chemical compound with the molecular formula C4H4S4. It is a sulfur-containing compound that is often used in organic synthesis and as a building block for pharmaceuticals and agrochemicals. Its unique structure and properties make it a valuable tool for researchers and chemists in the development of new compounds and materials. Additionally, 4,5-bis(methylthio)-1,3-dithiole-2-thione has attracted interest due to its potential biological and pharmacological activities, including its antioxidant, anti-inflammatory, and antimicrobial properties. Overall, this compound has a wide range of potential applications in various fields of research and industry.

InChI:InChI=1/C5H6S5/c1-7-3-4(8-2)10-5(6)9-3/h1-2H3

Upstream product

• 221296-97-5 Pd(1,2-bis(diphenylphosphanyl)ethane)(4-methylthio-2-thioxo-1,3-dithiole-5-thiolate₎₂ 
• 98-88-4 benzoyl chloride 
• 74-88-4 methyl iodide 

Downstream Products

• 51501-77-0 tetrakis(methylthio)tetrathiafulvalene 
• 1448894-61-8 C₂₄H₂₀Br₂S₈ 
• 365210-76-0 4-(4,5-bis-methylsulfanyl-[1,3]dithiol-2-ylidenemethyl)-benzaldehyde 

Relevant articles and documents

Experimental and theoretical studies on the mechanism of the C-S bond activation of PdII thiolate/thioether complexes

Two equivalents of L (L = 4-methylthio-2-thioxo-1,3-dithiole-5-thiolate or Medmit) react with cis-Pd- (PR3)2Cl2 (R = Ph and Et) to afford Pd(PR3)(η1-L)(η2-L) (R = Et: 1 ; R = Ph: 2) complexes, which have been characterized by X-ray crystallography. These compounds are dynamic in solution due to an exchange of the thiomethyl groups on palladium. Variable-temperature 1H NMR spectroscopy reveals a low coalescence temperature (173 K). Treatment of Pd(diphos)Cl2 (diphos = dppe or dppm) with 2 equiv of L affords thiolato complexes Pd(dppe)(η1-L)2 (3) and Pd(dppm)(η1-L)2 (4). Whereas 3 is rigid in solution with firm η2-coordination of dppe and η1-coordination of the thiolate, two linkage isomers Pd(η2-dppm)(η1-L)2 and Pd(η1-dppm)(η1-L)(η2-L) coexist in a solution of 4. L coordinated on PdII undergoes a S-demethylation reaction leading to dithiolene complexes and MeL. This transformation requires high temperature, and its efficiency depends on the nature of the phosphines as well as the nature of the metal (Pd vs Pt). DFT calculations reveal that the most likely mechanism depends on the lability of phosphines. Starting from M(PR3)2(η1- L)2 (M= Pd and Pt; R = Ph and Et), the favored sequence implies decoordination of one triethyl phosphine (M(PEt3)(η1-L)(η2- L)2 as intermediate) or two triphenylphosphines (Pd(η2-L)2 as intermediate) followed by oxidative addition and reductive elimination (OA/RE) reactions. In the case of PEt3, this OA/RE sequence can also compete with an intramolecular nucleophilic addition (AN), which can be described as an attack of a thiolate sulfur atom on a CH3+ carbocation. An intramolecular SN2 process was found to be the most feasible, starting from M(dppe)(η1-L)2 (M= Pd and Pt), with the nucleophile approaching the thiomethyl group at an angle of 180° with respect to the CCH3-S bond. The influence of the coligand has also been studied experimentally. Structurally characterized disulfide L-L dimer has been isolated upon reaction of 2 equiv of L with MCl2 (M = Pd and Pt).