((1R,4S)-7,7-Dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methanesulfonic acid

Base Information

• Chemical Name: ((1R,4S)-7,7-Dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methanesulfonic acid
• CAS No.: 35963-20-3
• Molecular Formula: C10H16O4S
• Molecular Weight: 232.301
• Hs Code.: 29147090
• European Community (EC) Number: 252-817-9
• UNII: Y6075I4FXE
• DSSTox Substance ID: DTXSID901019421
• Nikkaji Number: J208.233K
• Wikidata: Q27124274
• Metabolomics Workbench ID: 58815
• Mol file: 35963-20-3.mol

Synonyms:35963-20-3;((1R,4S)-7,7-Dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methanesulfonic acid;(1R)-(-)-Camphor-10-sulfonic acid;(-)-10-Camphorsulfonic Acid;Camphorsulfonic acid, (-)-;L(-)-Camphorsulfonic acid;(-)-camphorsulfonic acid;(1R)-(-)-10-Camphorsulfonic acid;UNII-Y6075I4FXE;Y6075I4FXE;EINECS 252-817-9;[(1R,4S)-7,7-dimethyl-2-oxo-1-bicyclo[2.2.1]heptanyl]methanesulfonic acid;(R)-camphorsulfonic acid;[(1R,4S)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonic acid;(r)-camphor-10-sulfonic acid;(1R)-(7,7-Dimethyl-2-oxobicyclo(2.2.1)hept-1-yl)methanesulphonic acid;[(1R,4S)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl]methanesulfonic acid;(s)-camphorsulfonic acid;L-Camphor-10-sulfonic acid;(1r)-10-camphorsulfonic acid;(-)-CSA;MFCD00064158;(1R)-[7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulphonic acid;L-(-)-Camphor-10-sulfonic acid;(-)csa;(1r)-camphorsulfonic acid;L-CAMPHORSULFONIC ACID;SCHEMBL839571;CHEBI:55401;MIOPJNTWMNEORI-XVKPBYJWSA-N;DTXSID901019421;(r)-(-)-10-camphorsulfonic acid;(R)-(-)-CSA;BCP21435;((1R,4S)-7,7-Dimethyl-2-oxobicyclo-[2.2.1]heptan-1-yl)methanesulfonic acid;AKOS015911844;AKOS016015262;(-)-10-CSA;Camphorsulfonic acid, (1R)-(-)-10-;AC-11634;AS-13392;(1R)-(-)-10-Camphorsulfonic acid, 98%;CS-0015820;EN300-208104;W-106648;Q27124274;(-)-Camphor-10-sulfonic acid, purum, >=98.0% (T);[(1R,4S)-7,7-dimethyl-2-oxo-norbornan-1-yl]methanesulfonic acid;((1R,4S)-7,7-Dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methanesulfonicacid;(-)-(1R)-7,7-DIMETHYL-2-OXOBICYCLO(2.2.1)HEPTANE-1-METHANESULFONIC ACID;BICYCLO(2.2.1)HEPTANE-1-METHANESULFONIC ACID, 7,7-DIMETHYL-2-OXO-, (1R,4S)-;[(1RS,4SR)-7,7-Dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonic Acid ((+/-)-10-Camphorsulfonic Acid)

Chemical Property of ((1R,4S)-7,7-Dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methanesulfonic acid

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 2.9E-10mmHg at 25°C
• Melting Point: 198 °C (dec.)(lit.)
• Refractive Index: -21.5 ° (C=5, H2O)
• Boiling Point: 467.7°C at 760 mmHg
• PKA: 1.17±0.50(Predicted)
• Flash Point: 236.6°C
• PSA: 79.82000
• Density: 1.331 g/cm³
• LogP: 2.35040
• Storage Temp.: 2-8°C
• Sensitive.: Hygroscopic
• Water Solubility.: soluble
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 232.07693016
• Heavy Atom Count: 15
• Complexity: 404

Purity/Quality:

≥ 99.00% ^*data from raw suppliers

(1R)-(?)-10-Camphorsulfonic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45-24/25-27

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1(C2CCC1(C(=O)C2)CS(=O)(=O)O)C
• Isomeric SMILES: CC1([C@H]2CC[C@@]1(C(=O)C2)CS(=O)(=O)O)C
• Uses: (1) It is also used for the racemization of optical isomers. (2) It can be applied to the resolution of intermediate or isomer in medicine. (3) It also could play a role as organic synthesis intermediates and resolving agent. 1R)-(-)-10-Camphorsulfonic acid is a chiral derivative of Camphor.It has the following uses: (1)It is also used for the racemization of optical isomers. (2) It can be applied to the resolution of intermediate or isomer in medicine. (3) It also could play a role as organic synthesis intermediates and resolving agent. (1R)-(-)-Camphor-10-sulfonic acid, is used as a pharamaceutical intermediate and also used as a chiral derivative of Camp. It can also be used as resolving agents for chiral amines and other cations.
• Production method: Camphor sulfonic acid is obtained from camphor and sulfuric acid by irradiation. This method involves: 1) Adding the camphor and acetic anhydride to the pot. 2) Mixing it and making it dissolved. 3) Dripping sulfuric acid after cooling. And the reaction should be maintained at 44-45 °C for 48 hours. Then cool it to 6-7 °C. 4) Crystallizing, filtrating, washing with a small amount of acetic acid crystals, and dry it to get camphor sulfonic acid.
• Physical properties: (1R)-(-)-10-Camphorsulfonic acid is a kind of prismatic crystals and its melting point is 193-195 ° C (decompose). It is Insoluble in ether and slightly soluble in glacial acetic acid and ethyl acetate. And it is and moisture in wet air.

Technology Process of ((1R,4S)-7,7-Dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methanesulfonic acid

There total 14 articles about ((1R,4S)-7,7-Dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methanesulfonic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.2%

(2R,3S)-2-(2,4-difluorophenyl)-3-(5-fluoro-4-pyrimidinyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol (1R)-10-camphorsulfonate (188416-34-4,137234-71-0) → (R)-10-camphorsulfonic acid (35963-20-3,61380-66-3)

Guidance literature:

(2R,3S)-2-(2,4-difluorophenyl)-3-(5-fluoro-4-pyrimidinyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol (1R)-10-camphorsulfonate; With potassium carbonate; In dichloromethane; water; pH=8.9;

In dichloromethane; cyclohexane; at 20 - 50 ℃; for 8h; Reagent/catalyst;

Reference yield: 38.0%

→ 7,7'-di-tert-butyl-5,5'-dimethyl-[3,3']bibenzofuranylidene-2,2'-dione + camphor-10-sulfonic acid (76-26-6,3144-16-9,5872-08-2,35963-20-3,61380-66-3)

Guidance literature:

Reference yield:

1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-one (736109-58-3,787517-91-3,68546-28-1) → camphor-10-sulfonic acid (76-26-6,3144-16-9,5872-08-2,35963-20-3,61380-66-3)

Guidance literature:

With sulfuric acid; acetic anhydride;

DOI:10.2174/1573406411208061133

upstream raw materials:

1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-one

brucine

10-camphorsufonic acid

camphor-10-sulfonic acid

Downstream raw materials:

(1S)-10-camphorsulfonic acid

(R)-10-camphorsulfonic acid

(1S,5R)-1-[2-fluoro-4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hexane [(1R,4S)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonic acid salt

(+)-((2-chlorophenyl)-6,7-dihydro-4H-thieno[3,2-c]pyrid-5-yl)acetic acid (1R)-(-)-camphor-10-sulfonate

Refernces

• 1、 Smuts, Jonathan P.,Hao, Xin-Qi,Han, Zhaobin,Parpia, Curran,Krische, Michael J.,Armstrong, Daniel W.. "Enantiomeric separations of chiral sulfonic and phosphoric acids with barium-doped cyclofructan selectors via an ion interaction mechanism". . p. 1282 - 1290. Retrieved 2014/02/14.
• 2、 -. "Reactive Extraction of Free Organic Acids from the Ammonium Salts Thereof". Page/Page column 12. . Retrieved 2010/08/22.