Dimethyl trithiocarbonate

Dimethyl trithiocarbonate is an organic compound with the chemical formula SC(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 OC(OCH3)2, where all three oxygen atoms are replaced with sulfur atoms. In terms of its name, dimethyl trithiocarbonate is derived from esterification of trithiocarbonic acid with methanethiol.

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)
  • InChI=1S/C3H6S3/c1-5-3(4)6-2/h1-2H3[1]
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

Properties

Dimethyl trithiocarbonate is a yellow liquid with a strong and very unpleasant smell.[2][3]

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.[4]

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. https://pubchem.ncbi.nlm.nih.gov/compound/Dimethyl-trithiocarbonate
  2. https://www.sigmaaldrich.com/GB/en/coa/ALDRICH/397180/MKBC1532
  3. https://www.sigmaaldrich.com/GB/en/sds/aldrich/397180
  4. https://www.trc-canada.com/product-detail/?D265370


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