Methanesulfonic anhydride

Methanesulfonic anhydride is the acid anhydride of methanesulfonic acid. Like methanesulfonyl chloride, it may be used to generate mesylates (methanesulfonyl esters). It is commercially available but may also be prepared by the reaction of phosphorus pentoxide with methanesulfonic acid at 80 °C.[2]

P₂O₅ + 6 CH₃SO₃H → 3 (CH₃SO₂)₂O + 2 H₃PO₄

Methanesulfonic anhydride

Names
IUPAC name methylsulfonyl methanesulfonate
Other names methanesulfonic acid methylsulfonyl ester
Identifiers
CAS Number	7143-01-3
3D model (JSmol)	Interactive image
ChemSpider	73591
ECHA InfoCard	100.027.675
PubChem CID	81560
InChI InChI=1S/C2H6O5S2/c1-8(3,4)7-9(2,5)6/h1-2H3 Key: IZDROVVXIHRYMH-UHFFFAOYSA-N InChI=1/C2H6O5S2/c1-8(3,4)7-9(2,5)6/h1-2H3 Key: IZDROVVXIHRYMH-UHFFFAOYAS
SMILES O=S(=O)(OS(=O)(=O)C)C
Properties
Chemical formula	C2H6O5S2
Molar mass	174.20 g/mol
Appearance	White solid
Density	0.92 g/ml[1]
Melting point	69.5–70 °C (157.1–158.0 °F; 342.6–343.1 K)[2]
Solubility in water	Hydrolysis
Solubility	Soluble in most aprotic organic solvents
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

See also

• Disulfuric acid
• Sodium pyrosulfate
• Acetic anhydride
• Trifluoromethanesulfonic anhydride

References

1. Wachtmeister, C. A.; Pring, B.; Osterman, Siv; Ehrenberg, L.; Brunvoll, J.; Bunnenberg, E.; Djerassi, Carl; Records, Ruth (1966). "The Synthesis of Some Tritium-labelled Mutagenic Alkyl Alkanesulfonates". Acta Chemica Scandinavica. 20: 908–910. doi:10.3891/acta.chem.scand.20-0908.
2. Field, Lamar; Settlage, Paul H. (March 1954). "Alkanesulfonic Acid Anhydrides". Journal of the American Chemical Society. 76 (5): 1222–1225. doi:10.1021/ja01634a005.