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Specifications
| Appearance: | Light yellow to yellow to brown liquid |
| Purity (GC): | 99% min |
| Identification - IR: | Comply with the target compound |
| Chiral Purity: | 99% min |
| ee: | 98% min |
| Water content: | 0.5% max |
Applications
1.1 Chiral Building Block in Organic Synthesis
This compound is a chiral carboxylic acid that serves as a stereochemically defined precursor in asymmetric synthesis.
Frequently used in the construction of complex molecules in pharmaceutical and fine chemical synthesis where chirality is crucial.
1.2 Intermediate in Pharmaceutical Research
Utilized in the synthesis of active pharmaceutical ingredients (APIs) or chiral auxiliaries.
Particularly relevant in the development of NSAIDs, prostaglandin analogs, or other bioactive molecules containing a cyclohexenyl moiety.
1.3 Asymmetric Catalysis and Ligand Design
Acts as a starting material for designing chiral ligands or auxiliaries in enantioselective catalysis, helping achieve high stereoselectivity in metal-catalyzed or organocatalyzed reactions.
1.4 Material and Polymer Chemistry
The compound's conjugated diene-like structure and carboxylic acid functionality make it useful in the design of functionalized monomers or additives in specialized materials.
Benefits
2.1 Enantiomerically Pure Form
The (S)-(-) configuration provides chirality control in synthetic chemistry, enabling the production of enantiomerically enriched or pure products, essential for biological activity in drug development.
2.2 Versatile Reactivity
The molecule contains both a carboxylic acid group and a double bond, offering multiple points of functionalization (e.g., esterification, amidation, hydrogenation, or halogenation).
2.3 Mild Handling Properties
As a small, non-volatile, solid acid, it is typically easy to handle, purify, and store, making it ideal for bench-scale and industrial applications.
2.4 Enhances Selectivity in Synthesis
Using this compound can improve diastereoselectivity and enantioselectivity in multi-step organic transformations, streamlining synthetic routes and reducing the need for resolution steps.
Conclusion
(S)-(-)-3-Cyclohexenecarboxylic acid (CAS 5708-19-0) is a valuable chiral building block with wide-ranging applications in pharmaceuticals, asymmetric catalysis, and fine chemicals. Its well-defined (S)-configuration, along with reactive functional groups, makes it a versatile and effective intermediate for synthesizing stereochemically complex compounds. As demand for enantiopure pharmaceuticals and catalysts continues to rise, this compound plays a vital role in enabling efficient, selective, and high-yielding synthetic processes.
