Camphorsulfonic acid

Base Information

• Chemical Name: Camphorsulfonic acid
• CAS No.: 5872-08-2
• Molecular Formula: C10H16O4S
• Molecular Weight: 232.301
• Hs Code.: 29147000
• European Community (EC) Number: 221-554-1,227-527-0,200-949-2
• DSSTox Substance ID: DTXSID60863113
• Nikkaji Number: J192.554G,J264.789C
• Wikipedia: Camphorsulfonic_acid
• Wikidata: Q414283
• Mol file: 5872-08-2.mol

Synonyms:10-camphorsulfonic acid;10-camphorsulfonic acid, (+-)-isomer;10-camphorsulfonic acid, (1R)-isomer;10-camphorsulfonic acid, (1S,4R)-(+)-isomer;10-camphorsulfonic acid, aluminum salt;10-camphorsulfonic acid, ammonium salt;10-camphorsulfonic acid, bismuth (3+) salt;10-camphorsulfonic acid, calcium salt;10-camphorsulfonic acid, piperazine salt;10-camphorsulfonic acid, sodium salt;solucampher

Chemical Property of Camphorsulfonic acid

Chemical Property:

• Appearance/Colour: white to off-white powder
• Melting Point: 203-206 °C (dec.)(lit.)
• Refractive Index: 1.5400 (estimate)
• Boiling Point: 344.46°C (rough estimate)
• PKA: 1.17±0.50(Predicted)
• PSA: 79.82000
• Density: 1.331 g/cm³
• LogP: 2.35040
• Storage Temp.: 2-8°C
• Sensitive.: Hygroscopic
• Water Solubility.: Soluble in water.
• 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

DL-10-CamphorsulfonicAcid ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Organic Acids
• Canonical SMILES: CC1(C2CCC1(C(=O)C2)CS(=O)(=O)O)C
• Uses: Pharmaceutical intermediates, optical split agent. Camphorsulfonic acid is an important organic synthesis intermediates, optical resolving agent. Due to its optical rotation, it is industrially applicable be the optical isomers for racemisation, and is also widely used as pharmaceutical intermediates such as for the production of intestinal disorder inhibitors, HIV improving agents and the like. Left and right handed camphorsulfonic acid is an important resolving agent for optically active amino acids, such as camphorsulfonic acid—a chiral ion-pairing reagent. It separates 5 substances—phenylpropanolamine, which has receptor-blocking action and cardiac inhibition and local anesthetic action effects; metoprolol, propranolol, epinephrine, salbutamol and atenolol. Camphor sulfonate made by camphorsulfonic acid for salting or other synthetic routes also has a wide range of uses. For example, camphor sulfonate is a veterinary central stimulant, which can stimulate the respiratory center and cause respiratory excitement, ; it is used for the treatment respiratory and circulatory acute disorders, resisting central nervous system poisoning; camphor ammonium sulfonate acts as a chiral ion pair reagent added to the mobile phase to separate the aromatic alcohol amine drug enantiomers. Figure 3: Camphor sulfonate (+)-Camphor-10-sulfonic acid is used as a resolving agent for chiral amines and other cations. It is involved in the preparation of active pharmaceutical ingredient such as trimetaphan camsilate, which is used to reduce bleeding during neurosurgery. Further, it is involved in the transglucosidation of methyl and ethyl D-glucopyranosides by alcoholysis.

Technology Process of Camphorsulfonic acid

There total 7 articles about Camphorsulfonic 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: 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

Reference yield:

→ camphor-10-sulfonic acid (76-26-6,3144-16-9,5872-08-2,35963-20-3,61380-66-3)

Guidance literature:

dl-Campher, H2SO4-Essigsaeureanhydrid;

upstream raw materials:

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

Camphor

(1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one

Downstream raw materials:

(1S)-10-camphorsulfonic acid

(R)-10-camphorsulfonic acid

ethyl 2-((tetrahydro-2H-pyran-2-yl)oxy)propanoate

Refernces

• 1、 -. "Polymorphic clopidogrel hydrogenesulphate form". . . Retrieved 2008/06/13.
• 2、 Majeed, Nesreen N.,Porte, Andrew L.. "Action of Red Light on Solid (+)-10-Bromo-2-chloro-2-nitrosocamphane: (i) Nuclear and Electron Paramagnetic Resonance Studies; (ii) Reaction Products; (iii) Solid-state Photolysis Reaction Mechanisms". . p. 1139 - 1146. Retrieved 2007/10/02.