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Methylsulfonylmethane

Methylsulfonylmethane
Methylsulfonylmethane
Dimethylsulfone
Names
IUPAC name
dimethyl sulfone
Preferred IUPAC name
methanesulfonylmethane
Other names
methyl sulfone
methylsulfonylmethane
sulfonylbismethane
DMSO2
Identifiers
67-71-0 YesY
3D model (Jmol) Interactive image
ChEBI CHEBI:9349 YesY
ChEMBL ChEMBL25028 YesY
ChemSpider 5978 YesY
ECHA InfoCard 100.000.605
KEGG C11142 YesY
PubChem 6213
RTECS number PB2785000
UNII 9H4PO4Z4FT YesY
Properties
C2H6O2S
Molar mass 94.13 g·mol−1
Appearance White crystalline solid
Density 1.45 g/cm3
Melting point 109 °C (228 °F; 382 K)
Boiling point 248 °C (478 °F; 521 K)
Hazards
Safety data sheet External MSDS
S-phrases S22 S24/25
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentine Reactivity (yellow): no hazard code Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point 143 °C (289 °F; 416 K)
Related compounds
Related compounds
DMSO
dimethyl sulfide
dimethyl sulfate
sulfolane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY  (what is YesYN ?)
Infobox references

Methylsulfonylmethane (MSM) is an organosulfur compound with the formula (CH3)2SO2. It is also known by several other names including DMSO2, methyl sulfone, and dimethyl sulfone. This colorless solid features the sulfonyl functional group and is considered relatively inert chemically. It occurs naturally in some primitive plants, is present in small amounts in many foods and beverages, and is marketed as a dietary supplement. It is also commonly found in the atmosphere above marine areas, where it is used as a carbon source by the airborne bacteria Afipia, and is found distinctively in human melanoma cells.

MSM and the corresponding sulfoxide dimethyl sulfoxide ((CH3)2SO, DMSO) have different physical properties. MSM is a white crystalline solid at STP (m.p. = 109 °C) whereas DMSO is a liquid under standard conditions. The sulfoxide is a highly polar aprotic solvent and is miscible with water; it is also an excellent ligand. MSM is less reactive than DMSO because the S-atom of the sulfone is already in its highest oxidation state (VI). Indeed, oxidation of the sulfoxide produces the sulfone, both under laboratory conditions and metabolically.

Because of its polarity and thermal stability, MSM is used industrially as a high-temperature solvent for both inorganic and organic substances. It is used as a medium in organic synthesis. For example, displacement of aryl chlorides by potassium fluoride can be usefully conducted in molten MSM. With a pKa of 31, it can be deprotonated with sodium amide, and the conjugate base is an effective nucleophile.

The LD50 (dose at which 50% of test subjects are killed by the high dosage) of MSM is greater than 17.5 grams per kilogram of body weight. In rats, no adverse events were observed after daily doses of 2 g MSM per kg of body weight. In a 90-day follow-up study, rats received daily MSM doses of 1.5 g/kg, and no changes were observed in terms of symptoms, blood chemistry or gross pathology.


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