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Revision as of 19:48, 10 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'StdInChIKey', 'CASNo').← Previous edit		Latest revision as of 17:44, 17 September 2024 edit undoCitation bot (talk | contribs)Bots5,429,585 edits Removed parameters. | Use this bot. Report bugs. | Suggested by Neko-chan | Category:CS1 maint: DOI inactive as of February 2024‎ | #UCB_Category 22/293
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	{{Chembox		{{Chembox
			| Verifiedfields = changed
	| Watchedfields = changed		| Watchedfields = changed
	| verifiedrevid = 396124358		| verifiedrevid = 460015608
	| ImageFile = 10-camphorsulfonic acid.svg		| ImageFileL1 = 10-camphorsulfonic acid.svg
	| ImageSize = 100px		| ImageSizeL1 = 100px
	| ImageName = Wireframe model of camphorsulfonic acid		| ImageNameL1 = Wireframe model of camphorsulfonic acid
			| ImageFileR1 = Camphorsulfonic-acid-from-xtal-3D-bs-17-view-5.png
			| ImageSizeR1 = 125px
	| PIN = (7,7-dimethyl-2-oxobicycloheptan-1-yl)methanesulfonic acid		| PIN = (7,7-dimethyl-2-oxobicycloheptan-1-yl)methanesulfonic acid
	| OtherNames = Reychler's acid; 2-Oxobornane-10-sulfonic acid		| OtherNames = Reychler's acid; 2-Oxobornane-10-sulfonic acid
	| Section1 = {{Chembox Identifiers		|Section1={{Chembox Identifiers
		⚫	| CASNo_Ref = {{cascite|correct|CAS}}
	| CASNo = <!-- blanked - oldvalue: 5872-08-2 -->
			| CASNo = 5872-08-2
⚫	| CASNo_Ref = {{Cascite|correct|??}}
		⚫	| CASNo1_Ref = {{cascite|correct|CAS}}
	| CASNo1 = 35963-20-3		| CASNo1 = 35963-20-3
	| CASNo1_Comment = (1''R'')		| CASNo1_Comment = (1''R'')
⚫	| CASNo1_Ref = {{Cascite|correct|??}}
			| CASNo2_Ref = {{cascite|correct|CAS}}
⚫	| PubChem = 18462
			| CASNo2 = 3144-16-9
	| PubChem_Ref = {{Pubchemcite|correct|PubChem}}
		⚫	| CASNo2_Comment = (1''S'')
⚫	| PubChem1 = 131278
			| UNII_Ref = {{fdacite|correct|FDA}}
⚫	| PubChem1_Comment = (1''R'')
			| UNII = D8D049375Q
	| PubChem1_Ref = {{Pubchemcite|correct|PubChem}}
			| UNII1_Ref = {{fdacite|correct|FDA}}
⚫	| PubChem2 = 218580
			| UNII1 = Y6075I4FXE
⚫	| PubChem2_Comment = (1''S'')
			| UNII1_Comment = (1''R'')
	| PubChem2_Ref = {{Pubchemcite|correct|PubChem}}
			| UNII2_Ref = {{fdacite|correct|FDA}}
⚫	| PubChem3 = 43833349
			| UNII2 = 9TLZ01S15L
⚫	| PubChem3_Comment = (4''R'')
			| UNII2_Comment = (1''S'')
	| PubChem3_Ref = {{Pubchemcite|correct|PubChem}}
⚫	| PubChem4 = 3057042
		⚫	| PubChem = 18462
	| PubChem4_Comment = (4''S'')
		⚫	| PubChem1 = 131278
	| PubChem4_Ref = {{Pubchemcite|correct|PubChem}}
		⚫	| PubChem1_Comment = (1''R'')
⚫	| ChemSpiderID = 17438
		⚫	| PubChem2 = 218580
⚫	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
			| PubChem2_Comment = (1''S'')
⚫	| ChemSpiderID1 = 116050
		⚫	| PubChem3 = 43833349
⚫	| ChemSpiderID1_Comment = (1''R'')
		⚫	| PubChem3_Comment = (4''R'')
⚫	| ChemSpiderID1_Ref = {{Chemspidercite|correct|ChemSpider}}
		⚫	| PubChem4 = 3057042
	| ChemSpiderID2 = 189449
	| ChemSpiderID2_Comment = (1''S'')		| PubChem4_Comment = (4''S'')
		⚫	| ChemSpiderID = 17438
⚫	| ChemSpiderID2_Ref = {{Chemspidercite|correct|ChemSpider}}
		⚫	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫	| ChemSpiderID3 = 2318313
		⚫	| ChemSpiderID1 = 116050
⚫	| ChemSpiderID3_Comment = (4''S'')
		⚫	| ChemSpiderID1_Comment = (1''R'')
	| ChemSpiderID3_Ref = {{Chemspidercite|correct|ChemSpider}}
		⚫	| ChemSpiderID1_Ref = {{chemspidercite|correct|ChemSpider}}
⚫	| EINECS = 227-527-0
	| UNNumber = 1759		| ChemSpiderID2 = 189449
			| ChemSpiderID2_Comment = (1''S'')
⚫	| MeSHName = 10-Camphorsulfonic+acid
	| ChEBI_Ref = {{ebicite|correct|EBI}}		| ChemSpiderID2_Ref = {{chemspidercite|correct|ChemSpider}}
		⚫	| ChemSpiderID3 = 2318313
		⚫	| ChemSpiderID3_Comment = (4''S'')
		⚫	| ChemSpiderID3_Ref = {{chemspidercite|correct|ChemSpider}}
		⚫	| EINECS = 227-527-0
			| UNNumber = 1759
		⚫	| MeSHName = 10-Camphorsulfonic+acid
			| ChEBI_Ref = {{ebicite|correct|EBI}}
	| ChEBI = 55379		| ChEBI = 55379
	| SMILES = CC1(C2CCC1(C(=O)C2)CS(=O)(=O)O)C		| SMILES = CC1(C2CCC1(C(=O)C2)CS(=O)(=O)O)C
	| SMILES1 = O=S(=O)(O)CC12C(=O)CC(CC1)C2(C)C		| SMILES1 = O=S(=O)(O)CC12C(=O)CC(CC1)C2(C)C
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}		| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChI = 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)		| StdInChI = 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)
		⚫	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChI1 = 1/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)
⚫	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChIKey = MIOPJNTWMNEORI-UHFFFAOYSA-N		| StdInChIKey = MIOPJNTWMNEORI-UHFFFAOYSA-N
	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
		⚫	| Beilstein = 2216194
	| StdInChIKey = MIOPJNTWMNEORI-UHFFFAOYSA-N
			}}
⚫	| Beilstein = 2216194}}
	| Section2 = {{Chembox Properties		|Section2={{Chembox Properties
	| C = 10 | H = 16 | O = 4 | S = 1		| C=10 | H=16 | O=4 | S=1
	| Appearance =		| Appearance =
	| Density =		| Density =
	| MeltingPt =		| MeltingPt = 195 °C (decomposes)
	| BoilingPt =		| BoilingPt =
	| Solubility =		| Solubility =
	| pKa = 1.2		| pKa = 1.2
	}}		}}
	| Section3 = {{Chembox Hazards		|Section3={{Chembox Hazards
	| ExternalMSDS =		| ExternalSDS =
	| FlashPt =		| FlashPt =
	| Autoignition =		| AutoignitionPt =
	}}		}}
	}}		}}
	'''Camphorsulfonic acid''', sometimes abbreviated '''CSA''' or '''10-CSA''' is a ]. Like typical ]s, it is a relatively strong acid that exists as a colourless solid that is soluble in organic solvents.		'''Camphorsulfonic acid''', sometimes abbreviated '''CSA''' or '''10-CSA''' is an ]. Like typical ]s, 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 ] with ] and ]:<ref>{{OrgSynth | title = D,L-10-Camphorsulfonic acid (Reychler's Acid) | author = Paul D. Bartlett and L. H. Knox | prep = cv5p0194 | year = 1973 | collvol = 5 | collvolpages = 194}}</ref>		This compound is commercially available. It can be prepared by sulfonation of ] with ] and ]:<ref>{{OrgSynth | title = D,L-10-Camphorsulfonic acid (Reychler's Acid) | first1 = Paul D.| last1= Bartlett | first2= L. H.| last2= Knox | doi = 10.15227/orgsyn.045.0012 | year = 1965 | volume = 45 | pages = 12}}</ref>
			:]
	:]
			Although this reaction appears to be a sulfonation of an unactivated methyl group, the actual mechanism is believed to involve a retro-], 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.<ref>{{Cite book|title=Advanced organic chemistry : reaction mechanisms|last=Brückner|first=Reinhard|date=2002|publisher=Harcourt/Academic Press |isbn= 9780080498805 |location= San Diego |oclc=269472848}}</ref>
⚫	In ], CSA and its derivatives can be used as ]s for chiral amines and other cations.<ref>{{cite journal | journal = Heterocycles | volume = 31 | pages = 353 | year = 1990 | doi = 10.3987/COM-89-5250 | title = Preparation of Enatiomerically Pure Decahydro-6H-isoquinonaphthyridines Utilizing the Openshaw-Whittaker Hexahydrobenzoquinolizinone Resolution | last1 = D. Clark | first1 = Robin | last2 = R. Kern | first2 = John | last3 = J. Kurz | first3 = Lilia | last4 = T. Nelson | first4 = Janis | issue = 2}}</ref><ref>André B. Charette "3-Bromocamphor-8-sulfonic Acid" Encyclopedia of Reagents for Organic Synthesis 2001, John Wiley & Sons. {{DOI|10.1002/047084289X.rb283}}</ref> For example, 3-bromocamphor-8-sulfonic acid was used in the synthesis of enantiopure ].<ref>{{cite journal | journal = ] | doi = 10.1021/jo00381a052 | title = Crystallization-induced asymmetric transformation: Stereospecific synthesis of a potent peripheral CCK antagonist | year = 1987 | last1 = Reider | first1 = Paul J. | last2 = Davis | first2 = Paul | last3 = Hughes | first3 = David L. | last4 = Grabowski | first4 = Edward J. J. | volume = 52 | issue = 5 | pages = 955–957}}</ref>
		⚫	In ], CSA and its derivatives can be used as ]s for chiral amines and other cations.<ref>{{cite journal | journal = Heterocycles | volume = 31 | pages = 353 | year = 1990 | doi = 10.3987/COM-89-5250 | title = Preparation of Enatiomerically Pure Decahydro-6H-isoquinonaphthyridines Utilizing the Openshaw-Whittaker Hexahydrobenzoquinolizinone Resolution | last1 = Clark | first1 = Robin D. | last2 = Kern | first2 = John R. | last3 = Kurz | first3 = Lilia J. | last4 = Nelson | first4 = Janis T. | issue = 2| doi-access = free }}</ref><ref>{{cite encyclopedia| first1= André B.| last1= Charette |title= 3-Bromocamphor-8-sulfonic Acid| encyclopedia= Encyclopedia of Reagents for Organic Synthesis |year= 2001| publisher= John Wiley & Sons| doi= 10.1002/047084289X.rb283| isbn= 0471936235}}</ref> The synthesis of ] was an example of this. 3-bromocamphor-8-sulfonic acid was used in the synthesis of enantiopure ].<ref>{{cite journal | journal = ] | doi = 10.1021/jo00381a052 | title = Crystallization-induced asymmetric transformation: Stereospecific synthesis of a potent peripheral CCK antagonist | year = 1987 | last1 = Reider | first1 = Paul J. | last2 = Davis | first2 = Paul | last3 = Hughes | first3 = David L. | last4 = Grabowski | first4 = Edward J. J. | volume = 52 | issue = 5 | pages = 955–957}}</ref>
			Camphorsulfonic acid is also being used for the synthesis of ].<ref>{{cite journal | journal = ] | doi = 10.1002/ejoc.201900325 | title = Microwave-Assisted Metal-Free Rapid Synthesis of C4-Arylated Quinolines via Povarov Type Multicomponent Reactiont | year = 2019 | last1 = Chandra | first1 = Devesh | last2 = Dhiman | first2 = Ankit K | last3 = Kumar | first3 = Rakesh | last4 = Sharma | first4 = Upendra | volume = 2019 | issue = 16 | pages = 2753–2758| s2cid = 107383202 }}</ref> Camphorsulfonic acid is used in some pharmaceutical formulations, where is it referred to as '''camsilate''' or '''camsylate''', including ] and ]. Some studies (c.f. Lednicer) support that D-CSA was used for the resolution of ].
	==References==		==References==
			{{reflist}}
	<References/>
	]		]
	]
	]
	]