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.[2][3]
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| Names | |
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| IUPAC name
Bis(methylsulfanyl)methanethione[1]
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| Preferred IUPAC name
Dimethyl trithiocarbonate | |
Other names
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| Identifiers | |
3D model (JSmol)
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PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| (CH3S)2CS | |
| Molar mass | 138.26 g·mol−1 |
| Appearance | Yellow liquid[2] |
| Odor | Stench[3] |
| Density | 1.254 g/cm3[2] |
| Melting point | −3 °C (27 °F; 270 K)[2] |
| Boiling point | 101–102 °C (214–216 °F; 374–375 K) at 16 hPa[2] |
Refractive index (nD)
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1.675[2] |
| Hazards | |
| Flash point | 97 °C (207 °F) |
| Related compounds | |
Related compounds
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Dimethyl carbonate |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Synthesis edit
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:[4]
- CSCl2 + 2 CH3SH → CS(SCH3)2 + 2 HCl
Alternatively, it can be prepared by treating carbon disulfide with aqueous base, a phase transfer reagent, and methyl iodide.[5]
Uses edit
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][2] Dimethyl trithiocarbonate is also a useful reagent in the preparation of 2-mercaptoquinoline and its analogues which are potential antileishmanial agents.[6]
Hazards and toxicity edit
Dimethyl trithiocarbonate is combustible. Upon catching fire, irritating, suffocating and toxic gases are released, like carbon oxides and sulfur oxides.[3]
References edit
- ^ a b c "Dimethyl trithiocarbonate".
- ^ a b c d e f g https://www.sigmaaldrich.com/GB/en/coa/ALDRICH/397180/MKBC1532
- ^ a b c https://www.sigmaaldrich.com/GB/en/sds/aldrich/397180
- ^ Godt, H. C.; Wann, R. E. (1961). "The Synthesis of Organic Trithiocarbonates1". The Journal of Organic Chemistry. 26 (10): 4047–4051. doi:10.1021/jo01068a097.
- ^ Lee, Albert W. M.; Chan, W. H.; Wong, H. C. (1988). "One Pot Phase Transfer Synthesis of Trithiocarbonates from Carbon Bisulphide and Alkyl Halides". Synthetic Communications. 18 (13): 1531–1536. doi:10.1080/00397918808081310.
- ^ "2314-48-9 | Dimethyl Trithiocarbonate | C₃H₆S₃ | TRC".
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