Dimethyl trithiocarbonate is an organic compound with the chemical formula S=C(SCH3)2. It is a methyl ester of trithiocarbonic acid. This chemical belongs to a subcategory of esters called thioesters. It is a sulfur analog of dimethyl carbonate O=C(OCH3)2, where all three oxygen atoms are replaced with sulfur atoms. Dimethyl trithiocarbonate is a yellow liquid with a strong and unpleasant odor.
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| IUPAC name Bis(methylsulfanyl)methanethione | |
| Preferred IUPAC name Dimethyl trithiocarbonate | |
Other names
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CompTox Dashboard (EPA) |
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| Properties | |
Chemical formula | (CH3S)2CS |
| Molar mass | 138.26 g·mol−1 |
| Appearance | Yellow liquid |
| Odor | Stench |
| Density | 1.254 g/cm3 |
| Melting point | −3 °C (27 °F; 270 K) |
| Boiling point | 101–102 °C (214–216 °F; 374–375 K) at 16 hPa |
Refractive index (nD) | 1.675 |
| Hazards | |
| Flash point | 97 °C (207 °F) |
| Related compounds | |
Related compounds | Dimethyl carbonate |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references | |
Synthesis
In terms of its name, dimethyl trithiocarbonate is formally derived by esterification of trithiocarbonic acid with methanethiol.
One synthesis starts from thiophosgene as described in this simplified equation:
- CSCl2 + 2 CH3SH → CS(SCH3)2 + 2 HCl
Alternatively, it can be prepared by treating carbon disulfide with aqueous base, a phase-transfer catalyst, and methyl iodide.
Uses
Dimethyl trithiocarbonate is used in preparation of methyl-β,β′-dicarbonyldithiocarboxylate derivatives,[clarification needed] in generation of tris(organothiyl)methyl radicals (RS)3C•,[why?] and in preparation of β-oxodithiocarboxylates.[clarification needed] Dimethyl trithiocarbonate is also a useful reagent in the preparation of 2-mercaptoquinoline and its analogues which are potential antileishmanial agents.
Hazards and toxicity
Dimethyl trithiocarbonate is combustible. Upon catching fire, irritating, suffocating and toxic gases are released, like carbon oxides and sulfur oxides.
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