(-)-Di-p-toluoyl-L-tartaric Acid丨CAS 32634-66-5

(-)-Di-p-toluoyl-L-tartaric acid, with the Chemical Abstracts Service (CAS) number 32634-66-5, is a chiral derivative of tartaric acid. It is widely used in organic synthesis, particularly for the resolution of racemic mixtures and as a chiral resolving agent. Its unique structure and properties make it valuable in pharmaceuticals, asymmetric synthesis, and chemical research.

- Melting Point: ~168-170°C (334-338°F)

- Solubility: Soluble in organic solvents like methanol, ethanol, and acetone; sparingly soluble in water.

- Structure: It consists of L-tartaric acid esterified with two p-toluoyl groups, making it a chiral molecule with specific stereochemical properties.

1. Chiral Resolution:

(-)-Di-p-toluoyl-L-tartaric acid丨32634-66-5 is widely used as a resolving agent to separate enantiomers from racemic mixtures. It forms diastereomeric salts with chiral amines, which can be separated based on their differing solubilities.

- This application is particularly important in the pharmaceutical industry, where the separation of enantiomers is critical for producing optically pure drugs.

2. Asymmetric Synthesis:

- It is used as a chiral auxiliary or catalyst in asymmetric synthesis to induce chirality in organic reactions, such as the synthesis of enantiomerically pure compounds.

3. Pharmaceuticals:

- The compound is used in the production of enantiomerically pure drugs, where the biological activity of a drug often depends on its specific stereochemistry. Examples include the synthesis of chiral intermediates for antihypertensive, antiviral, and anticancer drugs.

4. Chemical Research:

(-)-Di-p-toluoyl-L-tartaric acid丨32634-66-5 is used in laboratories to study chiral recognition, stereochemistry, and enantioselective reactions. It is also employed in the development of new chiral catalysts and resolving agents.

5. Coordination Chemistry:

- It is used to synthesize chiral metal complexes, which are important in catalysis and materials science.

1. High Enantioselectivity:

- The compound is highly effective in resolving racemic mixtures, providing enantiomerically pure products with high optical purity.

2. Versatility:

- Its applications span across pharmaceuticals, asymmetric synthesis, and chemical research, making it a versatile tool in organic chemistry.

3. Stability and Ease of Use:

(-)-Di-p-toluoyl-L-tartaric acid丨32634-66-5 is stable under standard conditions and easy to handle, making it a preferred choice for chiral resolution and synthesis.

4. Pharmaceutical Relevance:

- Its role in producing enantiomerically pure drugs ensures the efficacy and safety of pharmaceutical products, as the biological activity of drugs often depends on their stereochemistry.

5. Research Utility:

- It is a valuable tool for studying chiral recognition and developing new methods for asymmetric synthesis.

(-)-Di-p-toluoyl-L-tartaric acid丨32634-66-5 works by forming diastereomeric salts with chiral amines or other basic compounds. These salts have different physical properties, such as solubility, allowing for their separation through crystallization or chromatography. The resolved enantiomers can then be regenerated from the salts.

- (-)-Di-p-toluoyl-L-tartaric acid is generally safe to handle but should be used with standard laboratory precautions, including gloves, goggles, and proper ventilation.

- It should be stored in a cool, dry place, away from moisture and strong oxidizing agents, to maintain its stability.

- In case of contact with skin or eyes, rinse thoroughly with water and seek medical attention if irritation persists.

(-)-Di-p-toluoyl-L-tartaric acid丨32634-66-5 is a crucial chiral resolving agent with significant applications in pharmaceuticals, asymmetric synthesis, and chemical research. Its ability to separate enantiomers and induce chirality in organic reactions makes it an indispensable tool in the production of enantiomerically pure compounds. Proper handling and storage ensure its effectiveness and safety in various applications.