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 (Jmol)	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  (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:

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