(2R,5R)-1,6-Diphenyl-2,5-hexanediamine hydrochloride
[CAS# 1247119-31-8]

Identification

• Name: (2R,5R)-1,6-Diphenyl-2,5-hexanediamine hydrochloride
• Molecular Formula: C₁₈H₂₄N₂.2(HCl)
• Molecular Weight: 341.32
• CAS Registry Number: 1247119-31-8
• EC Number: 700-856-1
• SMILES: C1=CC=C(C=C1)C[C@@H](CC[C@H](CC2=CC=CC=C2)N)N.Cl.Cl

Properties

• Solubility: 0.00415 mg/ml (water)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P280-P301+P312-P302+P352-P305+P351+P338

Discovery and Applications

(2R,5R)-1,6-Diphenyl-2,5-hexanediamine hydrochloride is a chiral diamine compound that was discovered as part of efforts to develop new chiral catalysts and ligands in asymmetric synthesis. The compound was synthesized through a series of stereoselective reactions, allowing for the precise control of its stereochemistry. This particular configuration, (2R,5R), is critical for its application in enantioselective catalysis.

(2R,5R)-1,6-Diphenyl-2,5-hexanediamine hydrochloride is primarily utilized in asymmetric synthesis, a process crucial for the production of chiral molecules, which are essential in pharmaceuticals, agrochemicals, and fine chemicals. Its role as a chiral diamine ligand allows it to form complexes with various metals, such as palladium or rhodium, which are then used as catalysts in enantioselective reactions. These reactions can produce one enantiomer of a compound preferentially over another, a necessity for creating drugs that are effective and safe, as different enantiomers can have different biological activities.

In pharmaceutical chemistry, this compound is instrumental in synthesizing chiral intermediates and active pharmaceutical ingredients (APIs). Its ability to control the stereochemistry of the reaction products ensures the desired enantiomer is obtained, which can significantly affect the efficacy and safety profile of the drug. For instance, in the synthesis of certain beta-lactam antibiotics or chiral amine drugs, the use of (2R,5R)-1,6-diphenyl-2,5-hexanediamine hydrochloride can enhance the yield and selectivity of the desired enantiomer.

Beyond its pharmaceutical applications, (2R,5R)-1,6-diphenyl-2,5-hexanediamine hydrochloride is also valuable in academic research. It serves as a model compound in studying the mechanisms of asymmetric catalysis and the development of new chiral catalysts.

Additionally, in the field of materials science, this chiral diamine can be used to synthesize chiral polymers and materials with unique optical and mechanical properties. These materials have potential applications in areas such as chiral optics, sensing, and drug delivery systems, where the control of chirality is crucial.

References

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