Dimethyl trithiocarbonate

Dimethyl trithiocarbonate
Names
	IUPAC name Bis(methylsulfanyl)methanethione
	Preferred IUPAC name Dimethyl trithiocarbonate
	Other names Carbonotrithioic acid, dimethyl ester; Dimethyl carbonotrithioate; Trithiocarbonic acid, dimethyl ester;
Identifiers
CAS Number	2314-48-9 ;
3D model (JSmol)	Interactive image;
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
Odor	Stench
Density	1.254 g/cm3
Melting point	−3 °C (27 °F; 270 K)
Boiling point	101–102 °C (214–216 °F; 374–375 K) at 16 hPa
Refractive index (nD)	1.675
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

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]

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]

References

^ ^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".

[pubchem-1] "Dimethyl trithiocarbonate".

[sigmaaldrich1-2] ^ ^a ^b ^c ^d ^e ^f ^g https://www.sigmaaldrich.com/GB/en/coa/ALDRICH/397180/MKBC1532

[sigmaaldrich-3] ttps://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.

[trc-canada-6] "2314-48-9 | Dimethyl Trithiocarbonate | C₃H₆S₃ | TRC".

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