Dimethyl trisulfide
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| Names | |
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| IUPAC name
(methyltrisulfanyl)methane
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| Other names
2,3,4-trithiapentane
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| Identifiers | |
3658-80-8  |
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| ChemSpider | 18219 |
| Jmol 3D model | Interactive image |
| PubChem | 19310 |
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| Properties | |
| C2H6S3 | |
| Molar mass | 126.26 g/mol |
| Density | 1.1978 g/cm3 |
| Melting point | −68.05 °C (−90.49 °F; 205.10 K) |
| Boiling point | 170 °C (338 °F; 443 K) (65–68 °C @ 25 Torr) |
| Vapor pressure | {{{value}}} |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Infobox references | |
Dimethyl trisulfide (DMTS) is an organic chemical compound and the simplest organic trisulfide.[1][2] It is a flammable liquid with a foul odor, which is detectable at levels as low as 1 part per trillion.[3]
Occurrence
Dimethyl trisulfide has been found in volatiles emitted from cooked onion, leek and other Allium species, from broccoli and cabbage, as well as from Limburger cheese,[4] and is involved in the unpalatable aroma of aged beer and stale Japanese sake.[5] It is a decomposition product from bacterial decomposition, including from the early stages of human decomposition,[6] and is a major attractant for blowflies looking for hosts. 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.[7] DMTS contributes to the foul odor given off by the fungus Phallus impudicus, also known as the common stinkhorn. DMTS causes the characteristic malodorous smell of a fungating lesion, e.g., from cancer wounds,[3] and contributes to the odor of human feces.[8]
DMTS can be synthesized by the reaction of methanethiol with hydrogen sulfide (in the presence of copper (II))[9] and with sulfur dichloride,[10] among other methods:[2]
- 2 CH3SH + SCl2 → CH3SSSCH3 + HCl
Chemical reactions
On heating at 80 °C, DMTS slowly decomposes to a mixture of dimethyl di-, tri-, and tetrasulfides.[10] The reactivity of DMTS is related to its weak sulfur-sulfur bond (ca. 45 kcal/mol).[1] Dimethyl tetrasulfide, which is thermally more reactive than dimethyl trisulfide, has a still weaker (central) sulfur-sulfur bond (ca. 36 kcal/mol).[10] Oxidation of DMTS by meta-chloroperoxybenzoic acid (mCPBA) gives the corresponding S-monoxide, CH3S(O)SSCH3.[11]
Uses
Trap baits containing dimethyl trisulfide have been used to capture Calliphora loewi and other blowflies.[12]
References
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