D-Camphorsulfonic Acid Product Description CAS#3144-16-9

D-Camphorsulfonic acid (D-CSA), also known as dextrorotatory camphorsulfonic acid, (1S)-(+)-camphor-10-sulfonic acid, or Reychler's acid, has the chemical name (1S,4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptane-1-methanesulfonic acid, with the molecular formula C₁₀H₁₆O₄S and a molecular weight of 232.29. It is a white crystalline granule or crystalline powder at room temperature. Its melting point is 196–201°C, boiling point is 344°C, and density is 1.2981 g/mL (25°C). In terms of solubility, D-Camphorsulfonic acid is readily soluble in water and ethanol, insoluble in ether, and slightly soluble in glacial acetic acid and ethyl acetate. The specific rotation [a]D²⁰ is +20.0 to +23.0° (C=5, H₂O). D-camphor sulfonic acid is deliquescent in moist air. Industrially, D-camphor sulfonic acid is mainly produced by reacting camphor with sulfuric acid in the presence of acetic anhydride, followed by sulfonation and recrystallization for purification. D-camphor sulfonic acid is an important chiral Brønsted acid. Its molecule contains a sulfonic acid group and a chiral camphor skeleton, endowing it with unique acid catalytic activity and optical selectivity, making it valuable in organic synthesis, chiral resolution, pharmaceuticals, and other fields.

D-Camphorsulfonic Acid Product Applications CAS#3144-16-9

D-Camphorsulfonic acid is an important chiral organic synthesis intermediate and multifunctional reagent, widely used in pharmaceuticals, chemicals, daily chemicals, and scientific research.

In the field of chiral resolution, D-camphorsulfonic acid is one of the most commonly used chiral resolving agents. It can form diastereomer salts with chiral amines, alcohols, and carboxylic acids, allowing for the separation of enantiomers by crystallization or chromatography. The ability of D-camphorsulfonic acid to resolve enantiomers is crucial for the production of enantiomerically pure compounds, which is of great significance for the development of drugs and other chiral substances.

In organic synthesis, D-camphorsulfonic acid can serve as a highly efficient chiral Brønsted acid catalyst. It is an important chiral catalyst and ligand in asymmetric synthesis, catalyzing enantioselective Michael-type Friedel-Crafts reactions, Henry reactions, hydroxylation reactions, olefin epoxidation reactions, and the synthesis of chiral polyanilines. D-Camphorsulfonic acid is also a commonly used catalyst in natural product synthesis. In addition, D-camphorsulfonic acid can be used as a catalyst for dipeptide coupling and for asymmetric oxidation reactions of sulfides and disulfides.

In the pharmaceutical field, D-camphorsulfonic acid is an important pharmaceutical intermediate used in the synthesis of various chiral drugs. Its derivative, 10-camphorsulfonyl chloride, is an important starting material in chiral synthesis.