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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
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
Acidity (pKa) 1.2
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Camphorsulfonic acid, sometimes abbreviated CSA or 10-CSA is a organosulfur compound. Like typical sulfonic acids, it is a relatively strong acid that exists as a colourless solid that is soluble in organic solvents.

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

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

References

  1. Paul D. Bartlett and L. H. Knox (1973). "D,L-10-Camphorsulfonic acid (Reychler's Acid)". Organic Syntheses; Collected Volumes, vol. 5, p. 194.
  2. D. Clark, Robin; R. Kern, John; J. Kurz, Lilia; T. Nelson, Janis (1990). "Preparation of Enatiomerically Pure Decahydro-6H-isoquinonaphthyridines Utilizing the Openshaw-Whittaker Hexahydrobenzoquinolizinone Resolution". Heterocycles. 31 (2): 353. doi:10.3987/COM-89-5250.
  3. André B. Charette "3-Bromocamphor-8-sulfonic Acid" Encyclopedia of Reagents for Organic Synthesis 2001, John Wiley & Sons. doi:10.1002/047084289X.rb283
  4. 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.
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