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Chemical compound From Wikipedia, the free encyclopedia
Camphorsulfonic acid, sometimes abbreviated CSA or 10-CSA is an organosulfur compound. Like typical sulfonic 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.
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Names | |||
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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 | |||
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3D model (JSmol) |
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2216194 | |||
ChEBI | |||
ChemSpider | |||
ECHA InfoCard | 100.025.024 | ||
EC Number |
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MeSH | 10-Camphorsulfonic+acid | ||
PubChem CID |
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UNII |
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UN number | 1759 | ||
CompTox Dashboard (EPA) |
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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 their standard state (at 25 °C [77 °F], 100 kPa).
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This compound is commercially available. It can be prepared by sulfonation of camphor with sulfuric acid and acetic 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]
In organic synthesis, CSA and its derivatives can be used as resolving agents for chiral amines and other cations.[3][4] The synthesis of osanetant was an example of this. 3-bromocamphor-8-sulfonic acid was used in the synthesis of enantiopure devazepide.[5]
Camphorsulfonic acid is also being used for the synthesis of quinolines.[6] Camphorsulfonic acid is used in some pharmaceutical formulations, where is it referred to as camsilate or camsylate, including trimetaphan camsilate and lanabecestat camsylate. Some studies (c.f. Lednicer) support that D-CSA was used for the resolution of Chloramphenicol.
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