5616-51-3

Basic information

• Product Name: 2-METHYL-1,3-DITHIOLANE
• Synonyms: 2-methyl-3-dithiolane;3-Dithiolane,2-methyl-1;2-METHYL-1,3-DITHIACYCLOPENTANE;2-METHYL-1,3-DITHIOLANE;1,3-DITHIOLANE, 2-METHYL-;FEMA 3705;methyldithiolane,2-methyl-dithiacyclopentane,2-methyl-1,3-dithiolane;2-Methyl-1,3-dithiolane,97%
• CAS NO: 5616-51-3
• Molecular Formula: C₄H₈S₂
• Molecular Weight: 120.24
• EINECS: 227-038-2
• Mol File: 5616-51-3.mol

Chemical Properties

• Boiling Point: 40°C/2mmHg
• Flash Point: >100°(212°F)
• Appearance: clear colorless liquid
• Density: 1.15
• Vapor Pressure: 1.58mmHg at 25°C
• Refractive Index: 1.561
• CAS DataBase Reference: 2-METHYL-1,3-DITHIOLANE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-METHYL-1,3-DITHIOLANE(5616-51-3)
• EPA Substance Registry System: 2-METHYL-1,3-DITHIOLANE(5616-51-3)

Safety Data

• Statements: 20/21/22
• Safety Statements: 23-36/37/39-45
• RTECS: JP1163000
• TSCA: Yes
• Hazardous Substances Data: 5616-51-3(Hazardous Substances Data)

Usage

Uses

Used in Flavor and Fragrance Industry:
2-Methyl-1,3-dithiolane is used as a flavoring agent for its distinct burnt, alliaceous odor, adding a unique and desirable scent to various products in the flavor and fragrance industry.
Used in Chemical Synthesis:
2-Methyl-1,3-dithiolane serves as an important building block in the synthesis of various organic compounds, particularly those with sulfur-containing functional groups. Its chemical properties make it a versatile starting material for the development of new molecules with potential applications in various fields.
Used in Pharmaceutical Industry:
2-Methyl-1,3-dithiolane is used as an intermediate in the synthesis of pharmaceutical compounds, particularly those with potential therapeutic applications. Its unique chemical structure allows for the development of new drugs with improved efficacy and selectivity.
Used in Material Science:
2-Methyl-1,3-dithiolane can be utilized in the development of novel materials with specific properties, such as improved stability or reactivity. Its chemical structure can be incorporated into polymers, coatings, or other materials to enhance their performance in various applications.
Used in Analytical Chemistry:
2-Methyl-1,3-dithiolane can be employed as a reference compound or internal standard in analytical chemistry, particularly in the analysis of sulfur-containing compounds. Its distinct chemical properties and clear colorless liquid appearance make it an ideal candidate for such applications.

InChI:InChI=1/C4H8S2/c1-4-5-2-3-6-4/h4H,2-3H2,1H3

Upstream product

• 540-63-6 ethane-1,2-dithiol 
• 75-07-0 acetaldehyde 
• 107-06-2 1,2-dichloro-ethane 
• 627-51-0 divinyl sulfide 

Downstream Products

• 23230-01-5 2,3-dihydro-1,4-dithiin 
• 69824-34-6 [1-(2-Methylsulfanyl-ethylsulfanyl)-ethoxymethyl]-benzene 
• 69923-68-8 {3-Methyl-1-[1-(2-methylsulfanyl-ethylsulfanyl)-ethoxy]-butyl}-benzene 

Relevant articles and documents

1-oxo-1,3-dithiolanes-synthesis and stereochemistry

1-Oxo-1,3-dithiolane (4) and its cis- and trans-2-methyl (5,6), -4-methyl (7,8) and -5-methyl (9,10) derivatives were prepared by oxidizing the corresponding 1,3-dithiolanes (1-3) with NaIO4 in water. The oxides were purified and their isomers separated using thin layer chromatography. The structural characterization was carried out with 1H and 13C NMR spectroscopy and molecular modelling. The sulfoxides 4-6 and 8-10 attain two S(1) type envelopes (sometimes slightly distorted) the S=O ax envelope greatly dominating. Cis-4-methyl-1-oxo-1,3-dithiolane is a special case exhibiting both two closely related S=Oax (30 and 27%) as well as S=Oeq (21 and 22%) forms [S(1) and C(4) envelopes, respectively]. The relative energies of these conformations, the values of 1H-1H coupling constants and 1H and 13C chemical shifts were estimated by computational methods and they support well the conclusions based on the experimental data. Copyright

A novel application of 2-silylated 1,3-dithiolanes for the synthesis of aryl/hetaryl-substituted ethenes and dibenzofulvenes

Trimethylsilyldiazomethane (TMS-CHN2) reacts readily with hetaryl thioketones to give sterically crowded 2-trimethylsilyl- 4,4,5,5-tetrahetaryl-1,3-dithiolanes with complete regioselectivity at -75 °C as well as at rt. Thiofluorenone, a relatively stable and highly reactive aryl thioketone, yields upon treatment with TMS-CHN2at -60 °C the corresponding 1,3,4-thiadiazoline. This unstable cycloadduct undergoes decomposition at ca. -45 °C and the silylated thiocarbonyl S-methanide generated thereby is trapped with complete regioselectivity by aryl or hetaryl thioketones forming also sterically crowded 2-trimethylsilyl-1,3- dithiolanes. The obtained 1,3-dithiolanes, by treatment with an equimolar amount of TBAF in a one-pot procedure, are converted in high yields into hetaryl/aryl-substituted ethenes or dibenzofulvenes, respectively, via a cycloreversion reaction of the intermediate 1,3-dithiolane carbanion. The presented protocol offers a new, highly efficient approach to tetrasubstituted ethenes and dibenzofulvenes bearing aryl and/or hetaryl substituents.

Thermal degradation processes in polysulfide copolymers investigated by direct pyrolysis mass spectrometry and flash pyrolysis - Gas chromatography/mass spectrometry

This is the first report on the analysis of random block polysulfide copolymers containing different amounts of repeating units in the copolymer backbone, which has been studied by direct pyrolysis mass spectrometry (DPMS) and by pyrolysis-gas chromatography/mass spectrometry (Py-GC/MS). The homopolymers such as poly(ethylene sulfide) (PES), poly(styrene sulfide) (PSS), and two random copolymers, viz., poly(ethylene sulfidex-co-styrene sulfidey) [copolymer I (x = y = 0.5) and copolymer II (x = 0.74, y = 0.26)] were investigated by both DPMS and Py-GC/MS (except copolymer II) techniques. In the case of copolymer I, the thermal degradation products of SE1, SE2, S2, and S2E (S = styrene sulfide, E = ethylene sulfide) were detected in DPMS, whereas the formation of SE1 and SE2 were observed by Py-GC/MS technique. However, for copolymer II, SE3 was also found along with SE1, SE2, S2, and S2E in DPMS. The formation of additional product (SE3) observed in copolymer II could be due to an increase in the block length formed during copolymerization. Further, a comparative study on thermal degradation of PES, poly(ethylene disulfide) (PEDS), and poly(ethylene tetrasulfide) (PETS) were investigated by Py-GC/MS. The pyrolysis products detected by both DPMS and Py-GC/MS indicates that the thermal decomposition of these polymers yield cyclic sulfides through an intramolecular exchange or by backbiting processes. The linear products with thiol and vinyl groups were also observed by Py-GC/MS along with the cyclic products via carbon hydrogen transfer reaction.

Chemistry of peroxyacyl nitrates. Part III. The oxidation of thioethers by peroxyhexanoyl nitrate

The reaction of peroxyhexanoyl nitrate, 1a, a homologue of the atmospheric pollutant "PAN", 1b, with some twenty thioethers, is described.At 0-25 deg C, common thioethers such as Et2S or PhSMe are rapidly converted into sulfoxides in high yields in a variety of solvents, ranging from pentane and chloroform to acetic acid, methanol and aqueous acetonitrile.Rates are essentially solvent-independent, although the reaction is subject to marked steric hindrance.Relative rates for five p-substituted thioanisoles in MeOH at 22 deg C, leading to a Hammett ρ-value of -1.7, show that the sulfur atoms display nucleophilic character.Electron-attracting groups on α-carbon, such as in PhSCCl3 and in MeSCH2OC(O)Ph, inhibit the formation of sulfoxide.Addition of EtSH lowers the yield of sulfoxide, producing instead EtSSEt and EtSNO.Oxidation of Me2S by 1a with the NO2 group labelled by 18O does not give rise to 18O-enriched DMSO.Comparison of (CH3)2S with (CD3)2S revealed an inverse kinetic H/D isotope effect.The products obtained from 1a vary with solvent.In the presence of water or EtSH, hexanoic acid is formed, while methanol gives rise to methyl hexanoate, and in pentane/hexanoic acid, hexanoic anhydride is produced.In aprotic solvents, significant amounts of CO2 are formed.These observations can best be rationalized on the basis of an intermediate sulfurane R1R2S(ONO2)(OCOR), (I), produced from thioether R1SR2 and 1a, in the first step.The fate of (I) under various conditions is discussed.Finally, the features of the oxidation of thioethers by peroxyacylnitrate are compared with those of acyl peroxides and peroxy esters.It is suggested that in each case formation of a sulfurane may well be the first step.

Comparative radioprotective activity of various pentagonal compounds with two heteroatomes

Various heterocyclic compounds with two heteroatomes were synthesized and their potential radioprotective activity was tested. This study shows the interest of phenylthiazolidines derivatives in chemical radioprotection.