Methanesulfonamide
Chemical compound
From Wikipedia, the free encyclopedia
Methanesulfonamide is a chemical compound and the simplest representative of the substance group of sulfonic acid amides.
 | |
| Identifiers | |
|---|---|
3D model (JSmol) |
|
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.019.594 |
| EC Number |
|
PubChem CID |
|
CompTox Dashboard (EPA) |
|
| |
| |
| Properties | |
| CH5NO2S | |
| Molar mass | 95.12 g·mol−1 |
| Hazards | |
| GHS labelling: | |
 | |
| Warning | |
| H315, H319, H335 | |
| P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
| |
Preparation and synthesis
Methanesulfonamide is prepared by reacting methanesulfonyl chloride with ammonia.[1][2] Alternatively, the compound can be obtained by reacting the magnesium salt of methanesulfonic acid with hydroxylamine-O-sulfonic acid [3] or by reduction (here: the Staudinger reaction) of methanesulfonyl azide with triphenylphosphine in methanol.[4]
Properties
From a solution of methanesulfonamide in heptane, single crystals of the compound are obtained as semi-transparent, white tablets. X-ray structure analysis yields an O–S–O valence angle of 119°, which deviates significantly from the tetrahedral angle of 109.47°. At 161 picometers, the sulfur–nitrogen bond length is significantly shorter than that of a typical single bond (173 picometers) and corresponds to the shortened bond length observed in other sulfonamides. This is presumably caused by a coordinative bond between the lone pair of the amino group and the atomic orbital of the sulfur atom.[5]
Use
Various reagents for chemical syntheses can be produced from methanesulfonamide. For example, methanesulfonamide 1, p-toluenesulfonic acid 2 and 1,1-dimethoxy-2-(methylthio)ethane 3 yield N-(2-methylthio-1-p-toluenesufonylethyl)methanesulfonamide 4, a key compound in the synthesis of symmetrically substituted porphyrins.[1][6]
methanesulfonamide.svg)
In Sharpless dihydroxylation, the oxidation of olefins with potassium hexacyanidoferrate(III) and osmium(VIII) oxide to cis-vicinal-diols, methanesulfonamide acts as a catalyst in the final hydrolysis step during protonation of the osmium intermediate.[7]