3658-80-8

Basic information

• Product Name: Dimethyl trisulfide
• Synonyms: 1,3-Dimethyltrisulfane;2,3,4-Trithiapentane;CH3SSSCH3;dimethyl trisufide;DMTS;Trisulfide,dimethyl;DIMETHYL TRISULFIDE 98+%;Trimethyl trisulfide, 98+%
• CAS NO: 3658-80-8
• Molecular Formula: C₂H₆S₃
• Molecular Weight: 126.26
• EINECS: 222-910-9
• Product Categories: sulfide Flavor;DID - DINChromatography;Alphabetic;D;Life Sciences Standards;Natural Compounds;Natural CompoundsChemical Class;Other;Alphabetical Listings;C-D;Flavors and Fragrances
• Mol File: 3658-80-8.mol
• Article Data: 22

Chemical Properties

• Melting Point: −68 °C(lit.)
• Boiling Point: 58 °C15 mm Hg(lit.)
• Flash Point: 133 °F
• Appearance: Clear yellow/Liquid
• Density: 1.202 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.07mmHg at 25°C
• Refractive Index: n20/D 1.602(lit.)
• Water Solubility: Insoluble in water.
• BRN: 1731604
• CAS DataBase Reference: Dimethyl trisulfide(CAS DataBase Reference)
• NIST Chemistry Reference: Dimethyl trisulfide(3658-80-8)
• EPA Substance Registry System: Dimethyl trisulfide(3658-80-8)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38-36/38-20/22-10
• Safety Statements: 26-37/39-16-24/25
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• F: 10-23
• TSCA: Yes
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 3658-80-8(Hazardous Substances Data)

Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 3658-80-8 differently. You can refer to the following data:
1. clear yellow liquid
2. Dimethyl trisulfide has a powerful, diffusive, penetrating odor reminiscent of fresh onion

Occurrence

Reported as occurring in the volatile portion of fresh onion juice; the major aroma component in cooked vegetables of the Brassica genus. Also reported found in kohlrabi, cabbage, onion, garlic, shallots, leek, peas, mustard, tomato, wheaten bread, cheeses, milk, cooked chicken, pork, beef, hop oil, beer, brandies, whiskey, sherry, grape wine, cocoa, coffee, roasted peanuts, mushrooms, broccoli, cauliflower, brussels sprouts, radishes, pumpkin, sweet corn, asparagus, black tea, shellfish and squid.

Uses

Dimethyl trisulfide is reported as a major aroma component in cooked Brassicaceous vegetables. Trap baits containing dimethyl trisulfide have been used to capture Calliphora loewi and other blowflies. Dimethyl trisulfide along with dimethyl sulfide and dimethyl disulfide have been confirmed as volatile compounds given off by the fly-attracting plant known as dead-horse arum (Helicodiceros muscivorus). These flies are attracted to the odor of fetid meat and help pollinate this plant.

Preparation

It is produced by the microorganism, L. cremoris S2.

Taste threshold values

Taste characteristics at 2.0 ppm: sulfureous, alliaceous, gassy, savory and meaty with a fresh, vegetative nuance

Synthesis Reference(s)

Tetrahedron Letters, 30, p. 2995, 1989 DOI: 10.1016/S0040-4039(00)99178-0

InChI:InChI=1/C2H6S3/c1-3-5-4-2/h1-2H3

Upstream product

• 917-64-6 methyl magnesium iodide 
• 6251-26-9 methyl hydrodisulfide 
• 5813-48-9 Methanesulfenyl chloride 
• 624-92-0 Dimethyldisulphide 
• 74-88-4 methyl iodide 
• 107-31-3 Methyl formate 
• 7783-06-4 hydrogen sulfide 
• 74-93-1 methylthiol 
• 37488-76-9 sodium trisulfide 
• 77-78-1 dimethyl sulfate 
• 3385-94-2 hexamethyldisilathiane 
• 13882-12-7 S-methyl methanethiosulfinate 
• 42254-80-8 S-methyl thiosulfate O-sodium salt 
• 512-42-5 sodium methyl sulfate 

Downstream Products

• 74-93-1 methylthiol 
• 333-20-0 potassium thioacyanate 
• 1188540-66-0 [PPN][Fe2(μ-S)(nitrosyl)4(μ-methylthiolate)] 
• 5756-24-1 dimethyl tetrasulfide 
• 624-92-0 Dimethyldisulphide 
• 60779-24-0 butyl methyl disulfide 
• 188290-36-0 thiophene 
• 3326-88-3 1,2-dithiol-3-one 
• 2181-42-2 trimethylsulphonium iodide 
• 1357363-98-4 Ru(meso-tetrakis(4-methylphenyl)porphyrin)(MeSSSMe)2 
• 1357363-97-3 Ru(meso-tetrakis(2,4,6-trimethylphenyl)porphyrin)(MeSSSMe)2 

Relevant articles and documents

Allium discoloration: The color-forming potential of individual thiosulfinates and amino acids: Structural requirements for the color-developing precursors

Structural requirements for compounds involved in Allium discoloration have been investigated in detail. The abilities of all 20 protein amino acids and six naturally occurring 1-propenyl-containing thiosulfinates to form the pigments have been studied. Furthermore, several analogues of these thiosulfinates were prepared by synthesis, and their color-forming abilities were evaluated, together with those of various amino compounds. It has been found that an unsubstituted primary amino group and a free carboxyl group are essential structural features required for amino compounds to be able to generate the pigments. Out of the thiosulfinate analogues tested, only those containing at least a three-carbon chain with the β-carbon bearing a hydrogen atom yielded the pigments after reacting with glycine. Thiosulfonates, sulfoxides, sulfides, and disulfides did not form any colored products when mixed with glycine. The pH optimum for pigment formation has been found to be between 5.0 and 6.0 for all thiosulfinates tested.

Effect of Zinc Oxide on the Thermal Decomposition of Dimethyl Sulfoxide

Dimethyl sulfoxide (DMSO) is widely used in the chemical industry. However, it has a non-neglectful thermal runaway risk due to the nature of self-accelerating decomposition near the boiling point. Under the background that zinc oxide (ZnO) may extend the isothermal induction period of thermal decomposition of DMSO, this article conducts an in-depth study for the phenomenon with the techniques such as differential scanning calorimetry (DSC), accelerating rate calorimetry (ARC), gas chromatography-mass spectrometry (GC-MS), X-ray photoelectron spectroscopy (XPS), and X-ray diffractometry (XRD). After being mixed with ZnO, the maximum decomposition rate of DMSO was significantly reduced and the adiabatic induction period of DMSO decomposition was extended by 3.27 times, indicating that the thermal decomposition intensity of DMSO was obviously reduced. It was experimentally demonstrated that ZnO did not change the decomposition pathways of DMSO, but it could promote the decomposition of methanethiol, which was a decomposition intermediate of DMSO and could potentially serve as a promoter on the decomposition of DMSO.

Catalytic reactions of dimethyl disulfide with thiophene and benzene

The gas-phase reaction of dimethyl disulfide with thiophene proceeds under the action of acid catalysts under atmospheric pressure at 160-350°C and a residence time of τ = 0.6-21 s to form thioalkylation and alkylation products. Dimethyl disulfide reacts with benzene to form only alkylation products. Catalysts containing both strong protic and Lewis acid sites, as well as basic sites of moderate strength, are the most active ones.

Synthesis, stability, and reactivity of [(TPA)Zn(SH)]+ in aqueous and organic solutions

Reaction of the complex [(TPA)Zn(H2O)]2+ [TPA = tris(2-pyridylmethyl)amine] with hydrogen sulfide in aqueous buffered solution gives the corresponding monomeric hydrogensulfido complex [(TPA)Zn(SH)] +, which was fully characterized, including by XRD. This complex is stable at neutral pH, but decomposes under basic conditions to yield the free ligand and zinc sulfide, and under acidic conditions to give hydrogen sulfide and the starting aqua complex. In organic solvents, the coordinated sulfur atom reacts with electrophiles such as methylmethanethiosulfonate to yield methyltrisulfide. Reaction with the hydroxo complex [(TpPh,Me)Zn(OH)] [TpPh,Me = hydridotris{(5-methyl-3-phenyl)pyrazolyl}borate] promotes the formation of the unsymmetrical dinuclear μ-sulfido species [(TPA)Zn-S-Zn(TpPh,Me)]+, which, upon treatment with one molar equivalent of trifluoroacetic acid, dissociates into [(Tp Ph,Me)Zn(SH)] and [(TPA)Zn(CF3CO2)] +, resulting in the transfer of the hydrogensulfido ligand from one zinc center to another.