174500-20-0

Basic information

• Product Name: 2,6-Bis[(4S)-phenyl-2-oxazolin-2-yl]pyridine
• Synonyms: (S,S)-2,6-BIS(4-PHENYL-2-OXAZOLIN-2-YL)PYRIDINE;(S,S)-2,2'-(2,6-PYRIDINEDIYL)BIS(4-PHENYL-2-OXAZOLINE);[S-(R*,R*)]-2,6-BIS(4,5-DIHYDRO-4-PHENYL-2-OXAZOLYL)PYRIDINE;2,6-BIS[(4S)-PHENYL-2-(OXAZOLIN-2-YL)]PYRIDINE;(-)-2,6-BIS[(4S)-4-PHENYL-2-OXAZOLIN-2-YL]PYRIDINE;2,6-BIS-[(S)-4-PHENYL-4,5-DIHYDRO-OXAZOL-2-YL]-PYRIDINE;(-)-2,6-Bis[(4S)-4-phenyl-2-oxazolin-2-yl]pyridine,98+%;(s,s)-2,6-bis(4,5-dihydro-4-phenyl-2-oxazolyl)pyridine
• CAS NO: 174500-20-0
• Molecular Formula: C₂₃H₁₉N₃O₂
• Molecular Weight: 369.42
• Product Categories: Asymmetric Synthesis;Synthetic Organic Chemistry;organic amine;Heterocycle-Pyridine series;Furans ,Coumarins;BOX series;Chiral Nitrogen
• Mol File: 174500-20-0.mol

Chemical Properties

• Melting Point: 171-175 °C(lit.)
• Boiling Point: 600.4 °C at 760 mmHg
• Flash Point: 316.9 °C
• Appearance: white/crystal
• Density: 1.28 g/cm³
• Storage Temp.: Refrigerator
• PKA: 3.07±0.70(Predicted)
• Water Solubility: Insoluble
• CAS DataBase Reference: 2,6-Bis[(4S)-phenyl-2-oxazolin-2-yl]pyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-Bis[(4S)-phenyl-2-oxazolin-2-yl]pyridine(174500-20-0)
• EPA Substance Registry System: 2,6-Bis[(4S)-phenyl-2-oxazolin-2-yl]pyridine(174500-20-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39-37/39
• WGK Germany: 3
• Hazardous Substances Data: 174500-20-0(Hazardous Substances Data)

Usage

Chemical Properties

White solid

Reactions

1. Ligand for Copper catalyzed syn-selective Mukaiyama aldol reaction. 2. Ligand for Tin catalyzed anti-selective aldol reaction. 3. Ligand for Ytterbuim catalyzed desymmetrization of meso epoxides. 4. Ligand for Copper catalyzed enantioselective addition of terminal alkynes to imines. 5. Ligand for Scandium catalyzed enantioselective syn-selective ene reactions. 6. Ligand for Copper catalysed asymmetric alkynylation of cyclic azomethine Imines. 7. Ligand for Europium catalyzed asymmetric alpha amination. 8. Ligand for Indium catalyzed enantioselective construction of spiro-fused 2-oxindole/α-methylene-γ-butyrolactones. 9. Ligand for Copper catalyzed asymmetric azide-alkyne cycloaddition to quaternary oxindoles. 10. Ligand for Iron catalyzed enantioselective nitrene transfer to sulfides. 11. Ligand for Copper catalyzed enantioselective intramolecular propargylic amination. 12. Ligand for Copper catalyzed asymmetric hydroxylation. 13. Ligand for Scandium catalyzed dearomatization of 2-naphthols by electrophilic amination. 14. Ligand for Copper catalyzed asymmetric alkynylation of oxocarbenium ions to set diaryl tetrasubstituted stereoceters.

Upstream product

• 499-83-2 Pyridine-2,6-dicarboxylic acid 
• 3739-94-4 2,6-Pyridinedicarbonyl dichloride 
• 2893-33-6 pyridine-2,6-dinitrile 
• 56613-81-1 (S)-2-Amino-1-phenyl-1-ethanol 
• 20989-17-7 (2S)-2-phenylglycinol 
• 55309-58-5 pyridine-2,6-dicarboximidic acid dimethyl ester 
• 873654-26-3 Pyridine-2,6-dicarboxylic acid bis-[((S)-2-hydroxy-1-phenyl-ethyl)-amide] 

Relevant articles and documents

Kinetic resolution by copper-catalyzed azide-alkyne cycloaddition

The use of chiral pybox ligands imparts enantioselectivity to the Cu I-catalyzed azide-alkyne cycloaddition reaction, in the form of kinetic resolution of α-chiral azides and desymmetrization of gem-diazides. While levels of selectivity are modest, the results show unequivocally that the process benefits from ligand-accelerated catalysis.

An efficient and general one-pot method for the synthesis of chiral bis(oxazoline) and pyridine bis(oxazoline) ligands

An expeditious method for the synthesis of chiral box and pybox ligands is reported. The approach is based on a one-pot condensation reaction of chiral β-amino alcohols with a dinitrile using stoichiometric or catalytic amounts of zinc triflate. Yields gr

Synthesis of asymmetric iron-pybox complexes and their application to aziridine forming reactions

The synthesis of a series of iron-pybox complexes and their employment in the catalytic asymmetric aziridine forming reaction is presented. When AgSbF6 is used as an initiator, the i-pr- and t-bu-pybox complexes produce 47% of the cis-aziridine

Amino acid recognition of pyridine bis(oxazoline)-copper(II) complex in aqueous solvent

Enantioselective recognition of amino acids has been studied with C2-symmetric chiral pyridine bis(oxazoline)-copper(II) complexes at physiological pH condition. UV-visible titration revealed strong binding of submillimolar dissociation constan

Asymmetric ring opening of meso epoxides with TMSCN catalyzed by (pybox)lanthanide complexes.

The asymmetric ring opening of meso epoxides with TMSCN is catalyzed by (pybox)YbCl3 complexes, yielding the beta-trimethylsilyloxy nitrile ring-opened products with good enantioselectivities (83-92% ee). The reaction exhibits a second-order kinetic depen