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

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
CAS Number	2314-48-9 Y
3D model (JSmol)	Interactive image
ChemSpider	15959
PubChem CID	16840
CompTox Dashboard (EPA)	DTXSID90177710
InChI Key: IQWMXKTYXNMSLC-UHFFFAOYSA-N InChI=1S/C3H6S3/c1-5-3(4)6-2/h1-2H3
SMILES CSC(=S)SC
Properties
Chemical formula	(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)	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 catalyst, and methyl iodide.^[5]

Uses

2-Mercaptoquinoline, potential antileishmanial agent, a chemical prepared using dimethyl trithiocarbonate

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

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