Trithiolane
Chemical compound
From Wikipedia, the free encyclopedia
In the area of organosulfur chemistry, trithiolane refers to either of two families of heterocycles with the C2S3 rings:
- 1,2,3-trithiolanes with a C-C bond
structure of 1,2,3- and 1,2,4-trithiolane | |
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3D model (JSmol) |
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CompTox Dashboard (EPA) |
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| Properties | |
| C2H4S3 | |
| Molar mass | 124.23 g·mol−1 |
| Related compounds | |
Related compounds |
Dithiolane |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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parent: 1,2,3-trithiolane (registry number 6669–39–2), colorless liquid, boiling point = 224 °C
- 1,2,4-trithiolanes with only one S-S bond
parent: 1,2,4-trithiolane (registry number 289–16–7), colorless solid, melting point 74-75 °C
Occurrence
A 1,2,3-trithiolane arises from treating of norbornene with elemental sulfur.[1] The same reaction also gives the pentasulfide (pentathiepane).
1,2,4-Trithiolanes are volatile components of many foods, especially after cooking. The frying of chicken produces 3,5-dimethyl-, 3,5-diisobutyl-1,2,4-trithiolane, 3-methyl-5-butyl-, and 3-methyl-5-pentyl-1,2,4-trithiolanes.[2] Trithiolane itself contributes to the flavor of truffles.[3] 3,5-Dimethyltrithiolane is a component of the intense odor of durian.[4]
1,2,4-Trithiolanes can be made artificially from partial oxidation of a thiocarbonyl to the thiosulfine, and then dimerization.[5] In such cases the ring adduct is in quilibrium with the reagents, and so slowly decomposes back to thiocarbonyls and elemental sulfur.[5]: 945