Camphorsulfonic acid

Camphorsulfonic acid

Names
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 N 35963-20-3 (1R) Y 3144-16-9 N
3D model (JSmol)	Interactive image Interactive image
Beilstein Reference	2216194
ChEBI	CHEBI:55379 Y
ChemSpider	17438 Y 116050 (1R) Y 189449 (1S) Y 2318313 (4S) Y
ECHA InfoCard	100.025.024
EC Number	227-527-0
MeSH	10-Camphorsulfonic+acid
PubChem CID	18462 131278 (1R) 218580 (1S) 43833349 (4R) 3057042 (4S)
UNII	9TLZ01S15L N
UN number	1759
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-UHFFFAOYSA-N Y
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−1
Melting point	195 °C (decomposes)
Acidity (pKa)	1.2
Hazards
Safety data sheet	External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
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] The synthesis of osanetant was an example of this. 3-bromocamphor-8-sulfonic acid was used in the synthesis of enantiopure devazepide.^[4]

Camphorsulfonic acid is used in some pharmaceutical formulations, where is it referred to as camsilate or camsylate, including trimetaphan camsilate and lanabecestat camsylate.

References

1. ↑ Paul D. Bartlett and L. H. Knox (1973). "D,L-10-Camphorsulfonic acid (Reychler's Acid)". Org. Synth. ; Coll. Vol., 5, p. 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.