Trithioacetone
Chemical compound
From Wikipedia, the free encyclopedia
Trithioacetone (2,2,4,4,6,6-hexamethyl-1,3,5-trithiane) is an organic chemical with formula C
9H
18S
3. Its covalent structure is [–C(CH
3)
2–S–]
3, that is, a six-membered ring of alternating carbon and sulfur atoms, with two methyl groups attached to each carbon.[4][2] It can be viewed as a derivative of 1,3,5-trithiane, with methyl-group substituents for all of the hydrogen atoms in that parent structure.
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| Names | |
|---|---|
| Preferred IUPAC name
Hexamethyl-1,3,5-trithiane | |
| Other names
Trithioacetone[1] | |
| Identifiers | |
3D model (JSmol) |
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| 5-19-09-00119 | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.011.438 |
| EC Number |
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PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C9H18S3 | |
| Molar mass | 222.42 g·mol−1 |
| Odor | Unpleasant, sulfurous |
| Density | 1.0660 to 1.0700 g/mL[2] |
| Melting point | 21.8°C[3] |
| Boiling point | 107°C/10mmHg[2] |
Refractive index (nD) |
1.5390 to 1.5430[2] |
| Hazards | |
| GHS labelling: | |
 | |
| Warning | |
| H315, H319, H335 | |
| P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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The compound Trithioacetone is a stable cyclic trimer of thioacetone (propane-2-thione), which by itself is an unstable compound.[5][6] In contrast, the analogous trioxane compound, 2,2,4,4,6,6-hexamethyl-1,3,5-trioxane (Triacetone), with oxygen atoms in place of the sulfur atoms, seems to be unstable, while its corresponding monomer acetone (2-propanone) is stable.
Synthesis
Trithioacetone was first made in 1889 by Baumann and Fromm, by reaction of hydrogen sulfide with acetone.[6] In the presence of an acidified ZnCl
2 catalyst at 25 °C, one obtains a product that is 60–70% trithioacetone, 30–40% of 2,2-propanedithiol, and small amounts of two isomeric impurities, 3,3,5,5,6,6-hexamethyl-1,2,4-trithiane and 4-mercapto-2,2,4,6,6-pentamethyl-1,3-dithiane.[6] The product can also be obtained by pyrolysis of allyl isopropyl sulfide.[7][8]
Reactions
Pyrolysis of trithioacetone at 500–650 °C and 5–20 mm of Hg gives thioacetone, that can be collected by a cold trap at −78 °C.
Uses
Toxicity
See also
- 2,4,6-trimethyl-1,3,5-trithiane
- Hexamethylcyclotrisiloxane, an analog with a silicon-oxygen ring instead of a carbon-sulfur one.
- Hexamethylcyclotrisilazane, with a silicon-nitrogen ring.[13]
- 2,2,4,4,6,6-hexamethyl-1,3,5-triselena-2,4,6-tristannacyclohexane, with a tin-selenium ring.[14][15]