1,3,5-Trithiane
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| 1,3,5-Trithiane | |
|---|---|
 |
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| IUPAC name | 1,3,5-Trithiane |
| Other names | Thioformaldehyde trimer, Trimethylentrisulfide, Trimethylene trisulfide, Trithioformaldehyde, 1,3,5-Trithiacyclohexane, sym-Trithiane, Thioform, s-Trithiane |
| Identifiers | |
| CAS number | [291-21-4] |
| PubChem | |
| EINECS number | |
| SMILES | C1SCSCS1 |
| 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 | |
| Main hazards | Toxic (T) |
| NFPA 704 |
 1
1
0
|
| S-phrases | S22, S24/25 |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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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 in turn can be alkylated.[3]
- (CH2S)3 + RLi → (CH2S)2(CHLiS) + RH
- (CH2S)2(CHLiS) + R’Br → (CH2S)2(CHR’S) + LiBr
- (CH2S)2(CHR’S) + H2O → R’CHO + ….
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]
- (CH2S)3 + 9 Cl2 + 6 H2O → 3 ClCH2SO2Cl + 12 HCl
[edit] References
- ^ David R. Lide, ed. Handbook of Chemistry and Physics, 85th Edition, Internet Version 2005. CRC Press, 2005.
- ^ Bost, R. W.; Constable, E. W. "sym-Trithiane" Organic Syntheses, Collected Volume 2, p.610 (1943). http://www.orgsyn.org/orgsyn/pdfs/CV2P0610.pdf
- ^ Seebach, D.; Beck, A. K. “Aldehydes From sym-Ttrithiane: n-Pentadecanal” Organic Syntheses, Collected Volume 6, p.869 (1988). http://www.orgsyn.org/orgsyn/pdfs/CV6P0869.pdf
- ^ Paquette, L. A.; Wittenbrook, L. S. “2-Chlorothiirane 1,1-Dioxide” Organic Syntheses, Collected Volume 5, p.231 (1973). http://www.orgsyn.org/orgsyn/pdfs/CV5P0231.pdf
