{7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl}methanesulfonic acid

• ChemBase ID: 103092
• Molecular Formular: C10H16O4S
• Molecular Mass: 232.29664
• Monoisotopic Mass: 232.07692999
• SMILES: CC1(C)C2CCC1(CS(=O)(=O)O)C(=O)C2
• Canonical SMILES: O=C1CC2C(C1(CC2)CS(=O)(=O)O)(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)
• InChIKey: MIOPJNTWMNEORI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl}methanesulfonic acid
• IUPAC Traditional name: camphorsulfonic acid
• Synonyms: DL-CAMPHORSULFONIC ACID; (1S,4R)-7,7-Dimethyl-2-oxo-bicyclo[2.2.1]heptane-1-methanesulfonic Acid; (+)-Camphor-10-sulfonic Acid; (+)-β-Camphorsulfonic Acid; d-10-Camphorsulfonic Acid; (1S)-(+)-10-Camphorsulfonic Acid; (1R,4S)-7,7-Dimethyl-2-oxo-bicyclo[2.2.1]heptane-1-methanesulfonic Acid; (-)-Camphor-10-sulfonic Acid; (R)-Camphor-10-sulfonic Acid; L(-)-Camphor-10-sulfonic Acid; l-10-Camphorsulfonic Acid; (1R)-(-)-10-Camphorsulfonic Acid; D,L-Camphor sulphonic acid; (±)-CSA; (±)-Camphor-10-sulfonic acid; (7,7-Dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methanesulfonic acid; (7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl)methanesulfonic acid; (1S)-(+)-10-Camphorsulfonic acid; (1S)-Camphor-10-sulfonic acid; (+)-10-CAMPHORSULFONIC ACID; Reychler's acid; 2-Oxobornane-10-sulfonic acid; Camphorsulfonic acid; (+/-)-樟脑-10-磺酸

Database IDs

• CAS Number: 5872-08-2; 35963-20-3; 3144-16-9
• EC Number: 227-527-0; 221-554-1
• MDL Number: MFCD00074827
• Beilstein Number: 2216194; 3205973
• PubChem SID: 162090541
• PubChem CID: 18462
• CHEBI ID: 55379
• Chemspider ID: 17438
• MeSH Name: 10-Camphorsulfonic+acid
• Wikipedia Title: Camphorsulfonic_acid

CALCULATED PROPERTIES

• Acid pKa: -0.8099843
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -1.3937413
• LogD (pH = 7.4): -1.393791
• Log P: 0.9826071
• Molar Refractivity: 54.6607 cm^3
• Polarizability: 22.475769 Å^3
• Polar Surface Area: 71.44 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Water
• Apperance: White Solid; White to Off-White Solid
• Melting Point: >192°C (dec.); 194°C; 195-199°C; 203 - 206°C; ca 200°C dec.
• Hydrophobicity(logP): 0.636
• pKa: 1.2

Safety Information

• Storage Condition: 2-8°C, Desiccate; Refrigerator
• Storage Warning: Hygroscopic
• RTECS: DT5077100; ED1550000
• European Hazard Symbols: Corrosive (C)
• UN Number: 1759; UN3261
• Hazard Class: 8
• Packing Group: II; III
• Australian Hazchem: 2X
• Risk Statements: 34; R:34
• Safety Statements: 20-26-36/37/39-45-60; S:26-27/28-36/37/39-46-64
• EU Classification: C10
• EU Hazard Identification Number: 8B
• Emergency Response Guidebook(ERG) Number: 154
• TSCA Listed: 是
• GHS Pictograms: GHS05
• GHS Hazard statements: H314-H318
• GHS Precautionary statements: P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A

Product Information

• Purity: 95%; 95+%; 98%

DETAILS

MP Biomedicals - 05203796

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02150551

Resolving agent.

Toronto Research Chemicals - C175045

A chiral derivative of Camphor. Used in the preparation of a chiral recognition polymer that is used in the chiral separation of amino acids. A catalyst in direct animation of α-branched aldehydes (including important biological molecules such as α-Me phe

Toronto Research Chemicals - C175050

Used as a resolving agent, and as a catalyst for coupling dipeptides.

REFERENCES

• Guo, H. et al.: Polym. Preprints Am. Chem. Soc., 40, 506 (1999)
• Liu, C. et al.: Org. Lett., 13, 2638 (1999)
• Useful acid catalyst, giving high yields in the formation of THP ethers from alcohols; see, e.g.: J. Chem. Soc., Chem. Commun., 413 (1986); Org. Synth., 76, 178 (1998). Catalyst for cycloprotection of 1,2-diols with 1,2-Cyclohexanedione, A14401: Synlett, 793 (1996); Org. Synth., 75, 170 (1997). Preferred catalyst for the intramolecular cyclization of hydroxy epoxides to tetrahydrofurans or tetrahydropyrans: J. Am. Chem. Soc., 111, 5330 (1989).