Methanesulfonyl chloride
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| Names | |||
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IUPAC name
Methanesulfonyl chloride
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| Other names
Mesyl chloride
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| Identifiers | |||
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3D model (JSmol)
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| ChemSpider | |||
| ECHA InfoCard | 100.004.279 | ||
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PubChem CID
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| Properties | |||
| CH3ClO2S | |||
| Molar mass | 114.54 g·mol−1 | ||
| Appearance | colorless liquid | ||
| Density | 1.480 g/mL | ||
| Boiling point | 161 °C (322 °F; 434 K) 730 mmHg | ||
| Reacts | |||
| Hazards | |||
| Main hazards | Lachrymator, highly toxic, corrosive | ||
| Related compounds | |||
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Other anions
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Methanesulfonyl fluoride | ||
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 (what is   ?) |
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| Infobox references | |||
Methanesulfonyl chloride (mesyl chloride) is an organosulfur compound with the formula CH3SO2Cl. It is a colourless liquid that dissolves in polar organic solvents but is reactive toward water, alcohols, and many amines. The simplest organic sulfonyl chloride, it is used to make methanesulfonates and to generate the elusive molecule sulfene.
It is manufactured by the reaction of methane and sulfuryl chloride in a radical reaction:
Another method of manufacture entails chlorination of methanesulfonic acid with thionyl chloride or phosgene:
Methanesulfonyl chloride is a precursor to many compounds because it is highly reactive. It is an electrophile, functioning as a source of the "CH3SO2+" group.
Methanesulfonyl chloride is mainly used to give methanesulfonates by its reaction with alcohols in the presence of a non-nucleophilic base. Methanesulfonates are used as intermediates in substitution reactions, elimination reactions, reductions, and rearrangement reactions. When treated with a Lewis acid, oxime methanesulfonates undergo facile Beckmann rearrangement.
Methanesulfonates are occasionally used as a protecting group for alcohols. They are stable to acidic conditions and is cleaved back to the alcohol using sodium amalgam.
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