Camphorsulfonic acid

Camphorsulfonic acid
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
CAS number 5872-08-2 Y, 35963-20-3 (1R) Y
PubChem 18462, 131278 (1R), 218580 (1S), 43833349 (4R), 3057042 (4S)
ChemSpider 17438 Y, 116050 (1R) Y, 189449 (1S) Y, 2318313 (4S) Y
EC number 227-527-0
UN number 1759
MeSH 10-Camphorsulfonic+acid
ChEBI CHEBI:55379 Y
Beilstein Reference 2216194
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C10H16O4S
Molar mass 232.3 g mol−1
Acidity (pKa) 1.2
Hazards
MSDS External MSDS
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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:[1]

In organic synthesis, CSA and its derivatives can be used as resolving agents for chiral amines and other cations.[2][3] For example, 3-bromocamphor-8-sulfonic acid was used in the synthesis of enantiopure devazepide.[4]

References

  1. ^ Paul D. Bartlett and L. H. Knox (1973), "D,L-10-Camphorsulfonic acid (Reychler's Acid)", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv5p0194 ; Coll. Vol. 5: 194 
  2. ^ D. Clark, Robin; R. Kern, John; J. Kurz, Lilia; T. Nelson, Janis (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. 
  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.