S,S'-Dimethyl dithiocarbonate

S,S'-Dimethyl dithiocarbonate is an organic compound with the chemical formula OC(SCH3)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(OCH3)2), where the two oxygen atoms from the −OCH3 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.

S,S'-Dimethyl dithiocarbonate
S,S'-Dimethyl dithiocarbonate molecule
Names
IUPAC name
S,S'-Dimethyl dithiocarbonate
Systematic IUPAC name
S,S-Dimethyl carbonodithioate[1]
Other names
  • Bis(methylsulfanyl)methanone[1]
  • Carbonodithioic acid S,S-dimethyl ester[1]
  • Dithiocarbonic acid S,S'-dimethyl ester[2]
  • S,S-Dimethyl dithiocarbonate[1]
Identifiers
3D model (JSmol)
1421112
ChEMBL
ChemSpider
ECHA InfoCard 100.106.322 Edit this at Wikidata
EC Number
  • InChI=1S/C3H6OS2/c1-5-3(4)6-2/h1-2H3
    Key: IUXMJLLWUTWQFX-UHFFFAOYSA-N
  • CSC(=O)SC
Properties
OC(SCH3)2
Molar mass 122.20 g·mol−1
Appearance Colorless liquid[2]
Density 1.1705 g/cm3[3]
Boiling point 169 °C (336 °F; 442 K)[2]
1.5485[4]
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H227, H302
P210, P264, P270, P280, P301+P312+P330, P301+P317, P330, P370+P378, P403+P235, P501
Flash point 62 °C (144 °F)[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Uses

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S,S'-Dimethyl dithiocarbonate is used as a dehydrating agent in chemistry and as a carbonylating agent.[5] It can be used as a source of a methanethiolate (CH3S).[2]

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

Hazards and toxicity

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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 (CO2), and sulfur dioxide (SO2), are released. It may react violently with strong oxidizing agents.[6]

References

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  1. ^ a b c d e "S,S'-Dimethyl dithiocarbonate". pubchem.ncbi.nlm.nih.gov.
  2. ^ a b c d e "S,S'-Dimethyl Dithiocarbonate 868-84-8 | TCI AMERICA". www.tcichemicals.com.
  3. ^ https://www.sigmaaldrich.com/GB/en/sds/aldrich/660191
  4. ^ https://www.sigmaaldrich.com/GB/en/product/aldrich/660191
  5. ^ "868-84-8 | S,S'-Dimethyl Dithiocarbonate | Carbonodithioic Acid S,S-Dimethyl Ester; Dithiocarbonic Acid S,S-Dimethyl Ester; Dithiocarbonic Acid S,S'-Dimethyl Ester; NSC 227849 | C3H6OS2 | TRC".
  6. ^ https://www.trc-canada.com/prod-img/MSDS/D473320MSDS.pdf