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Camphorsulfonic acid

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Camphorsulfonic acid
Wireframe model of camphorsulfonic acid
Wireframe model of camphorsulfonic acid
Names
Preferred IUPAC name (7,7-dimethyl-2-oxobicycloheptan-1-yl)methanesulfonic acid
Other names Reychler's acid; 2-Oxobornane-10-sulfonic acid
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 2216194
ChEBI
ChemSpider
ECHA InfoCard 100.025.024 Edit this at Wikidata
EC Number
  • 227-527-0
MeSH 10-Camphorsulfonic+acid
PubChem CID
UNII
UN number 1759
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C10H16O4S/c1-9(2)7-3-4-10(9,8(11)5-7)6-15(12,13)14/h7H,3-6H2,1-2H3,(H,12,13,14)Key: MIOPJNTWMNEORI-UHFFFAOYSA-N
SMILES
  • CC1(C2CCC1(C(=O)C2)CS(=O)(=O)O)C
  • O=S(=O)(O)CC12C(=O)CC(CC1)C2(C)C
Properties
Chemical formula C10H16O4S
Molar mass 232.29 g·mol
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 , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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.

This compound is commercially available. It can be prepared by sulfonation of camphor with sulfuric acid and acetic anhydride:

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.

In organic synthesis, CSA and its derivatives can be used as resolving agents for chiral amines and other cations. The synthesis of osanetant was an example of this. 3-bromocamphor-8-sulfonic acid was used in the synthesis of enantiopure devazepide.

Camphorsulfonic acid is also being used for the synthesis of quinolines. 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.

References

  1. Bartlett, Paul D.; Knox, L. H. (1965). "D,L-10-Camphorsulfonic acid (Reychler's Acid)". Organic Syntheses. 45: 12. doi:10.15227/orgsyn.045.0012.
  2. Brückner, Reinhard (2002). Advanced organic chemistry : reaction mechanisms. San Diego: Harcourt/Academic Press. ISBN 9780080498805. OCLC 269472848.
  3. Clark, Robin D.; Kern, John R.; Kurz, Lilia J.; Nelson, Janis T. (1990). "Preparation of Enatiomerically Pure Decahydro-6H-isoquino[2,1-g][1,6]naphthyridines Utilizing the Openshaw-Whittaker Hexahydrobenzo[a]quinolizinone Resolution". Heterocycles. 31 (2): 353. doi:10.3987/COM-89-5250.
  4. Charette, André B. (2001). "3-Bromocamphor-8-sulfonic Acid". Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons. doi:10.1002/047084289X.rb283. ISBN 0471936235.
  5. Reider, Paul J.; Davis, Paul; Hughes, David L.; Grabowski, Edward J. J. (1987). "Crystallization-induced asymmetric transformation: Stereospecific synthesis of a potent peripheral CCK antagonist". J. Org. Chem. 52 (5): 955–957. doi:10.1021/jo00381a052.
  6. Chandra, Devesh; Dhiman, Ankit K; Kumar, Rakesh; Sharma, Upendra (2019). "Microwave-Assisted Metal-Free Rapid Synthesis of C4-Arylated Quinolines via Povarov Type Multicomponent Reactiont". Eur. J. Org. Chem. 2019 (16): 2753–2758. doi:10.1002/ejoc.201900325. S2CID 107383202.
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