Chemistry:S,S'-Dimethyl dithiocarbonate

Short description: S,S'-Dimethyl dithiocarbonate

S,S'-Dimethyl dithiocarbonate

Names
IUPAC name S,S'-Dimethyl dithiocarbonate
Systematic IUPAC name S,S-Dimethyl carbonodithioate
Other names Bis(methylsulfanyl)methanone Carbonodithioic acid S,S-dimethyl ester Dithiocarbonic acid S,S'-dimethyl ester S,S-Dimethyl dithiocarbonate
Identifiers
CAS Number	868-84-8 Y
3D model (JSmol)	Interactive image
Beilstein Reference	1421112
ChEMBL	ChEMBL4796378
ChemSpider	277261
EC Number	617-931-9
PubChem CID	313474
InChI InChI=1S/C3H6OS2/c1-5-3(4)6-2/h1-2H3 Key: IUXMJLLWUTWQFX-UHFFFAOYSA-N
SMILES CSC(=O)SC
Properties
Chemical formula	OC(SCH 3) 2
Molar mass	122.20 g·mol−1
Appearance	Colorless liquid
Density	1.1705 g/cm3
Boiling point	169 °C (336 °F; 442 K)
Refractive index (nD)	1.5485
Hazards
GHS pictograms
GHS Signal word	Warning
GHS hazard statements	HH227Category:GHS errors, HH302Category:GHS errors
GHS precautionary statements	PP210Category:GHS errors, PP264Category:GHS errors, PP270Category:GHS errors, PP280Category:GHS errors, PP301+P312+P330Category:GHS errors, PP301+P317Category:GHS errors, PP330Category:GHS errors, PP370+P378Category:GHS errors, PP403+P235Category:GHS errors, PP501Category:GHS errors
Flash point	62 °C (144 °F)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

S,S'-Dimethyl dithiocarbonate is an organic compound with the chemical formula OC(SCH
3)
2. It is a colorless liquid. It is a methyl ester of dithiocarbonic S,S-acid (OC(SH)
2). It is a thioester (the prefix thio- means that an oxygen atom in the compound is replaced by a sulfur atom). It is an analog of dimethyl carbonate (OC(OCH
3)
2), where the two oxygen atoms from the –OCH
3 groups are replaced by sulfur atoms. In terms of the name of this thioester, it is derived from an esterification of dithiocarbonic S,S-acid with methanethiol.

Uses

S,S'-Dimethyl dithiocarbonate is used as a dehydrating agent in chemistry and as a carbonylating agent. It can be used as a source of a methanethiolate (CH₃S⁻).

Alkanethiolation reaction using S,S'-dimethyl dithiocarbonate, tetrabutylammonium bromide and aqueous solution of potassium hydroxide

Hazards and toxicity

S,S′-Dimethyl dithiocarbonate is a skin, eye, and respiratory system irritant; it can be absorbed into the body through the skin, causing damage to the body. It may cause damage to gastrointestinal system if it is swallowed. S,S′-Dimethyl dithiocarbonate is combustible. Upon catching fire, irritating and toxic fumes and gases, such as carbon monoxide (CO), carbon dioxide (CO
2), and sulfur dioxide (SO
2), are released. It may react violently with strong oxidizing agents.