Sulfonmethane

Sulfonmethane (sulfonomethane, sulfonal, acetone diethyl sulfone) is a chemical compound first synthesized by Eugen Baumann in 1888 and introduced as a hypnotic drug by Alfred Kast later on, but now superseded by newer and safer sedatives. Its appearance is either in colorless crystalline or powdered form. In United States, it is scheduled as a Schedule III drug in the Controlled Substance Act.

Sulfonmethane

Clinical data
ATC code	none
Legal status
Legal status	US: Schedule III
Identifiers
IUPAC name 2,2-bis(ethylsulfonyl)propane
CAS Number	115-24-2 N
PubChem CID	8262
ChemSpider	7964 Y
UNII	W00D22B592
CompTox Dashboard (EPA)	DTXSID3048574
ECHA InfoCard	100.003.704
Chemical and physical data
Formula	C7H16O4S2
Molar mass	228.32 g·mol−1
3D model (JSmol)	Interactive image
SMILES O=S(=O)(C(C)(C)S(=O)(=O)CC)CC
InChI InChI=1S/C7H16O4S2/c1-5-12(8,9)7(3,4)13(10,11)6-2/h5-6H2,1-4H3 Y Key:CESKLHVYGRFMFP-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

Chemistry

Sulfonal is prepared by condensing acetone with ethyl mercaptan in the presence of hydrochloric acid, the mercaptol (CH₃)₂C(SC₂H₅)₂ formed being subsequently oxidized by potassium permanganate. It is also formed by the action of alcoholic potash and methyl iodide on ethylidene diethyl sulfine, CH₃CH(SO₂C₂H₅)₂ (which is formed by the oxidation of dithioacetal with potassium permanganate). It crystallizes in prisms melting at 125 C, which are practically insoluble in cold water, but dissolves in 15 parts of hot water and also in alcohol and ether.

See also

• Trional
• Tetronal

Further reading

• Kast A (1888). Sulfonal, ein neues Schlafmittel (in German). Berlin.{{cite book}}: CS1 maint: location missing publisher (link)
• Wendt EC (1888). "Sulfonal, a new Hypnotic". The Medical Record. 33 (22). New York: 597–598.
• Bayer (1889). "Sulfonal". The Cincinnati Lancet-Clinic. 22. Cincinnati: J. C. Culbertson: 2.