Dimethyl trithiocarbonate

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]

Dimethyl trithiocarbonate
Dimethyl trithiocarbonate molecule
Names
IUPAC name
Bis(methylsulfanyl)methanethione[1]
Preferred IUPAC name
Dimethyl trithiocarbonate
Other names
  • Carbonotrithioic acid, dimethyl ester
  • Dimethyl carbonotrithioate
  • Trithiocarbonic acid, dimethyl ester
[1]
Identifiers
3D model (JSmol)
  • Key: IQWMXKTYXNMSLC-UHFFFAOYSA-N
  • InChI=1S/C3H6S3/c1-5-3(4)6-2/h1-2H3
  • CSC(=S)SC
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]
1.675[2]
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:[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
2-Mercaptoquinoline, potential antileishmanial agent, a chemical prepared by involving dimethyl trithiocarbonate

Dimethyl trithiocarbonate is used in preparation of methyl-β,β′-dicarbonyldithiocarboxylate derivatives, in generation of tris(organothiyl)methyl radicals (RS)3C•, and in preparation of β-oxodithiocarboxylates.[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

Dimethyl trithiocarbonate is combustible. Upon catching fire, irritating, suffocating and toxic gases are released, like carbon oxides and sulfur oxides.[3]

References
  1. "Dimethyl trithiocarbonate".
  2. https://www.sigmaaldrich.com/GB/en/coa/ALDRICH/397180/MKBC1532
  3. https://www.sigmaaldrich.com/GB/en/sds/aldrich/397180
  4. 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.
  5. 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.
  6. "2314-48-9 | Dimethyl Trithiocarbonate | C₃H₆S₃ | TRC".


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