D(+)-Camphorsulfonic Acid (CAS No. 3144-16-9)

D(+)Camphor Sulfonic Acid, also known as (1R)-(+)-10-camphorsulfonic acid, is a chiral organosulfur compound celebrated for its role as a Brønsted acid catalyst and resolving agent in stereoselective synthesis. With the chemical formula C₁₀H₁₆O₄S, it appears as a white to off-white crystalline powder that is highly soluble in polar solvents.

Item name

Index

Content

≥99.0%

Ignition residue

≤2.0%

Ignition residue

≤0.5%

Specific rotation

[α]20D:+21°-(+23)°(C=5, 1NHCl)

Melting point

197℃-200℃

D(+)Camphor Sulfonic Acid Applications and Uses

D(+)Camphor Sulfonic Acid’s inherent chirality and acidity enable targeted applications in advanced synthesis and analysis:

  • Asymmetric Catalysis: Acts as a chiral Brønsted acid catalyst in enantioselective reactions, such as aldol additions, Diels-Alder cycloadditions, and Mannich reactions for producing optically active pharmaceuticals.
  • Chiral Resolution: Employed as a resolving agent to separate enantiomers of amines, amino acids, and alcohols via diastereomeric salt formation, crucial for drug purity.
  • Polymer Synthesis: Serves as a stabilizer and dopant in the electrochemical synthesis of chiral polyaniline (PANI) nanofibers, enhancing conductivity and stereoregularity.
  • Pharmaceutical Intermediates: Key reagent in the production of enantiopure intermediates for antibiotics, antidepressants, and cardiovascular drugs.
  • Material Science: Utilized in the modification of polymers and as an additive in chiral stationary phases for HPLC enantiomer separation.

Its high enantiomeric excess (>99% ee in many processes) makes it a benchmark for stereocontrolled manufacturing.

Safety and Handling

D(+)Camphor Sulfonic Acid is corrosive, causing severe skin burns and eye damage upon contact. It is harmful if swallowed or inhaled and may irritate respiratory tracts. Essential handling guidelines include:

  • Storage: Store in a cool, dry place (<25°C) in tightly sealed containers under inert atmosphere; protect from moisture to prevent caking.
  • Handling: Wear PPE including acid-resistant gloves, goggles, and protective clothing. Use in a fume hood; avoid dust formation and direct contact.
  • Environmental Impact: Moderately toxic to aquatic organisms; neutralize spills with base and dispose as hazardous waste per regulations.
  • Regulatory Compliance: UN 1759 (Class 8, PG II); complies with GHS (H314: Causes severe skin burns and eye damage) and REACH/TSCA standards.

Request the Safety Data Sheet (SDS) for detailed exposure limits and first aid.

Frequently Asked Questions (FAQs)

What is the primary use of D(+)-Camphorsulfonic acid?

It is mainly utilized as a chiral catalyst in asymmetric synthesis and as a resolving agent for separating enantiomers in pharmaceutical production.

Is D(+)-Camphorsulfonic acid safe for laboratory use?

It is corrosive and requires PPE and ventilation, but poses no flammability risks; safe with proper protocols in controlled environments.

What is the shelf life of D(+)-Camphorsulfonic acid?

Under dry, sealed storage at room temperature, it maintains stability for 2-3 years, with no significant loss of optical activity or acidity.

Can D(+)-Camphorsulfonic acid be shipped internationally?

Yes, it is shipped globally under UN 1759 regulations, in moisture-proof packaging like HDPE bottles or drums for lab-scale to bulk volumes.

How does D(+)-Camphorsulfonic acid differ from L(-)-Camphorsulfonic acid?

The D(+) enantiomer induces the opposite stereochemistry in reactions compared to the L(-) form, allowing selection based on desired enantiomeric outcome while sharing identical physical properties.

Is D(+)-Camphorsulfonic acid soluble in non-polar solvents?

It has limited solubility in non-polar solvents like hexane but excels in polar media such as water and alcohols, ideal for aqueous-phase chiral resolutions.

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