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	3144-16-9Template:Scifinder, 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
SMILES CC1(C2CCC1(C(=O)C2)CS(=O)(=O)O)C O=S(=O)(O)CC12C(=O)CC(CC1)C2(C)C
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) Y Key: MIOPJNTWMNEORI-UHFFFAOYAN N
Properties
Molecular formula	C10H16O4S
Molar mass	232.30 g mol−1
Acidity (pKa)	1.2
Hazards
MSDS	External MSDS
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

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:^[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. ; 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.