Camphorsulfonic acid

Camphorsulfonic acid
Wireframe model of 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 ; 35963-20-3 (1R) ; 3144-16-9 (1S) ;
3D model (JSmol)	Interactive image; Interactive image;
Beilstein Reference	2216194
ChEBI	CHEBI:55379 ;
ChemSpider	17438 ; 116050 (1R) ; 189449 (1S) ; 2318313 (4S) ;
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	D8D049375Q ; Y6075I4FXE (1R) ; 9TLZ01S15L (1S) ;
UN number	1759
CompTox Dashboard (EPA)	DTXSID60863113 ;
	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−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).
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	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]

Although this reaction appears to be a sulfonation of an unactivated methyl group, the actual mechanism is believed to involve a retro-semipinacol rearrangement, deprotonation next to the tertiary carbocation to form an alkene, sulfonation of the alkene intermediate, and finally, semipinacol rearrangement to re-establish the ketone function.[2]

In organic synthesis, CSA and its derivatives can be used as resolving agents for chiral amines and other cations.[3][4] The synthesis of osanetant was an example of this. 3-bromocamphor-8-sulfonic acid was used in the synthesis of enantiopure devazepide.[5] Recently Camphorsulfonic acid is also being used for the synthesis of quinolines[6]

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

References

Paul D. Bartlett and L. H. Knox (1973). "D,L-10-Camphorsulfonic acid (Reychler's Acid)". Organic Syntheses.; Collective Volume, 5, p. 194
1955-, Brückner, Reinhard (2002). Advanced organic chemistry : reaction mechanisms. San Diego: Harcourt/Academic Press. ISBN 9780080498805. OCLC 269472848.CS1 maint: numeric names: authors list (link)
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.
André B. Charette "3-Bromocamphor-8-sulfonic Acid" Encyclopedia of Reagents for Organic Synthesis 2001, John Wiley & Sons. doi:10.1002/047084289X.rb283
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.
Chandra, Devesh; Dhiman, Ankit K; Kumar, Rakesh; Sharma, Upendra (2019). "Microwave‐Assisted Metal‐Free Rapid Synthesis of C4‐Arylated Quinolines via Povarov Type Multicomponent Reactiont". Eur. J. Org. Chem. 2019 (16): 2753–2758. doi:10.1002/ejoc.201900325.

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[1] Paul D. Bartlett and L. H. Knox (1973). "D,L-10-Camphorsulfonic acid (Reychler's Acid)". Organic Syntheses.; Collective Volume, 5, p. 194

[2] 1955-, Brückner, Reinhard (2002). Advanced organic chemistry : reaction mechanisms. San Diego: Harcourt/Academic Press. ISBN 9780080498805. OCLC 269472848.CS1 maint: numeric names: authors list (link)

[3] 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.

[4] André B. Charette "3-Bromocamphor-8-sulfonic Acid" Encyclopedia of Reagents for Organic Synthesis 2001, John Wiley & Sons. doi:10.1002/047084289X.rb283

[5] 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.

[6] Chandra, Devesh; Dhiman, Ankit K; Kumar, Rakesh; Sharma, Upendra (2019). "Microwave‐Assisted Metal‐Free Rapid Synthesis of C4‐Arylated Quinolines via Povarov Type Multicomponent Reactiont". Eur. J. Org. Chem. 2019 (16): 2753–2758. doi:10.1002/ejoc.201900325.