| 1,3,5-Trithiane | |
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1,3,5-Trithiane |
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Other names
Thioformaldehyde trimer, Trimethylentrisulfide, Trimethylene trisulfide, Trithioformaldehyde, 1,3,5-Trithiacyclohexane, sym-Trithiane, Thioform, s-Trithiane |
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| Identifiers | |
| CAS number | 291-21-4 |
| PubChem | 9264 |
| ChemSpider | 8907 |
| EC number | 206-029-7 |
| ChEBI | CHEBI:39196 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C3H6S3 |
| Molar mass | 138.27 |
| Appearance | Colourless solid |
| Density | 1.6374 g/cm3[1] |
| Melting point |
215-220 °C |
| Solubility in water | Slightly soluble |
| Solubility | Benzene |
| Hazards | |
| S-phrases | S22, S24/25 |
| Main hazards | Toxic (T) |
| NFPA 704 |
1
1
0
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| (verify) (what is: /?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
1,3,5-Trithiane is the chemical compound with the formula (CH2S)3. This heterocycle is the cyclic trimer of the otherwise unstable species thioformaldehyde. It consists of a six-membered ring with alternating methylene and thioether groups. It is prepared by treatment of formaldehyde with hydrogen sulfide.[2]
Trithiane is a building block molecule in organic synthesis, being a masked source of formaldehyde. In one application, it is deprotonated with organolithium reagents to give the lithium derivative, which can be alkylated.[3]
Trithiane is the dithioacetal of formaldehyde. Other dithioacetals undergo similar reactions to the above.
It is also a precursor to other organosulfur reagents. For example, chlorination in the presence of water affords the chloromethylsulfonyl chloride:[4]