Dimethyl trithiocarbonate

Last updated
Dimethyl trithiocarbonate
Dimethyl trithiocarbonate molecule.png
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)
ChemSpider
PubChem CID
  • 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
AppearanceYellow 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).

Dimethyl trithiocarbonate is an organic compound with the chemical formula S=C(SCH 3)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]

Contents

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 2-Mercaptoquinoline.png
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]

References

  1. 1 2 "Dimethyl trithiocarbonate".
  2. 1 2 3 4 5 6 7 https://www.sigmaaldrich.com/GB/en/coa/ALDRICH/397180/MKBC1532
  3. 1 2 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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