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| Names | |||
|---|---|---|---|
| Preferred IUPAC name (7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methanesulfonic acid | |||
| Other names Reychler's acid; 2-Oxobornane-10-sulfonic acid | |||
| Identifiers | |||
| |||
3D model (JSmol) | |||
| 2216194 | |||
| ChEBI | |||
| ChemSpider | |||
| ECHA InfoCard | 100.025.024 | ||
| EC Number |
| ||
| MeSH | 10-Camphorsulfonic+acid | ||
| UNII |
| ||
| UN number | 1759 | ||
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| Properties | |||
| C10H16O4S | |||
| Molar mass | 232.29 g·mol−1 | ||
| Melting point | 195 °C (decomposes) | ||
| Acidity (pKa) | 1.2 | ||
| Hazards | |||
| Safety data sheet (SDS) | External MSDS | ||
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |||
Camphorsulfonic acid, sometimes abbreviatedCSA or10-CSA is anorganosulfur compound. Like typicalsulfonic acids, it is a relatively strong acid that is a colorless solid at room temperature and is soluble in water and a wide variety of organic substances.
This compound is commercially available. It can be prepared by sulfonation ofcamphor withsulfuric acid andacetic anhydride:[1]
Although this reaction appears to be a sulfonation of an unactivated methyl group, the actual mechanism is believed to involve a retro-semipinacol rearrangement, deprotonation next to the tertiary carbocation to form an alkene, sulfonation of the alkene intermediate, and finally, semipinacol rearrangement to re-establish the ketone function.[2]
Inorganic synthesis, CSA and its derivatives can be used asresolving agents for chiral amines and other cations.[3][4] The synthesis ofosanetant was an example of this. 3-bromocamphor-8-sulfonic acid was used in the synthesis of enantiopuredevazepide.[5]
Camphorsulfonic acid is also being used for the synthesis ofquinolines.[6] Camphorsulfonic acid is used in some pharmaceutical formulations, where is it referred to ascamsilate orcamsylate, includingtrimetaphan camsilate andlanabecestat camsylate. Some studies (c.f. Lednicer) support that D-CSA was used for the resolution ofChloramphenicol.
