128249-70-7

Basic information

• Product Name: 2,6-Bis[(4R)-4-phenyl-2-oxazolinyl]pyridine
• Synonyms: 2,6-Bis[(4R)-4-phenyl-2-oxazolinyl]pyridine;2,6-BIS[(4R)-PHENYL-2-(OXAZOLIN-2-YL)]PYRIDINE;(R,R)-2,6-Bis(4,5-dihydro-4-phenyl-2-oxazolyl)pyridine;(R,R)-2,6-BIS(4-PHENYL-2-OXAZOLIN-2-YL)PYRIDINE;(r,r)-2,6-bis(4-phenyl-2-oxazolinyl)pyridine;(R,R)-2,2'-(2,6-PYRIDINEDIYL)BIS(4-PHENYL-2-OXAZOLINE);[R-(R,R)]-2,6-BIS(4,5-DIHYDRO-4-PHENYL-2-OXAZOLYL)PYRIDINE;(R-(R*,R*))-2,6-bis(4,5-dihydro-4-phenyl-2-oxazol
• CAS NO: 128249-70-7
• Molecular Formula: C₂₃H₁₉N₃O₂
• Molecular Weight: 369.42
• Product Categories: Asymmetric Synthesis;Synthetic Organic Chemistry;organic amine;Heterocycle-Pyridine series;BOX series;Chiral Nitrogen
• Mol File: 128249-70-7.mol
• Article Data: 7

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: 1.286 g/cm³
• Vapor Pressure: 9.72E-14mmHg at 25°C
• Refractive Index: 1.673
• Storage Temp.: Refrigerator
• PKA: 3.07±0.70(Predicted)
• Water Solubility: Insoluble
• CAS DataBase Reference: 2,6-Bis[(4R)-4-phenyl-2-oxazolinyl]pyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-Bis[(4R)-4-phenyl-2-oxazolinyl]pyridine(128249-70-7)
• EPA Substance Registry System: 2,6-Bis[(4R)-4-phenyl-2-oxazolinyl]pyridine(128249-70-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• WGK Germany: 3
• Hazardous Substances Data: 128249-70-7(Hazardous Substances Data)

Usage

Reactions

Ligand for Copper catalyzed syn-selective Mukaiyama aldol reaction. Ligand for Tin catalyzed anti-selective aldol reaction. Ligand for Ytterbuim catalyzed desymmetrization of meso epoxides. Ligand for Copper catalyzed enantioselective addition of terminal alkynes to imines. Ligand for Scandium catalyzed enantioselective syn-selective ene reactions. Ligand for Copper catalysed asymmetric alkynylation of cyclic azomethine Imines. Ligand for Europium catalyzed asymmetric alpha amination.

Chemical Properties

White needles

Uses

2,6-Bis[(4R)-4-phenyl-2-oxazolinyl]pyridine [Pybox] may be used as a chiral ligand in the copper-catalyzed enatioselective arylation of N-arylated tetrahydroisoquinolines (THIQs) with arylboronic acids in the presence of a photoredox catalyst.

InChI:InChI=1/C23H19N3O2/c1-3-8-16(9-4-1)20-14-27-22(25-20)18-12-7-13-19(24-18)23-26-21(15-28-23)17-10-5-2-6-11-17/h1-13,20-21H,14-15H2/t20-,21-/m1/s1

Upstream product

• 499-83-2 Pyridine-2,6-dicarboxylic acid 
• 2893-33-6 pyridine-2,6-dinitrile 
• 56613-80-0 D-2-phenylglycinol 
• 3739-94-4 2,6-Pyridinedicarbonyl dichloride 
• 661464-60-4 N,N-bis((R)-2'-hydroxy-1'-phenylethyl)pyridine-2,6-dicarboxamide 
• 5431-44-7 2,6-Pyridinedicarboxaldehyde 
• 5453-67-8 2,6-bis(methoxycarbonyl)pyridine 

Relevant articles and documents

Concise synthesis of conformationally constrained pybox ligands

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Surfactant-Assisted Nanocrystalline Zinc Coordination Polymers: Controlled Particle Sizes and Synergistic Effects in Catalysis

Different morphologies and particle sizes of two crystalline zinc-based coordination polymers (CPs), [Zn(pytz)H2O]n (1; H2pytz=2,6-bis(tetrazole)pyridine) and [Zn2(pytz)24H2O] (2), from the bulk scale to the nanoscale, could be obtained under solvothermal conditions with different surfactants (polyvinylpyrrolidone (PVP) or polyethylene glycol (PEG) 2000) as templates. PVP and PEG 2000 could act as capping and structure-directing agents, respectively, to influence the growth of crystalline particles and control their sizes. CP 1 exhibits a two-dimensional framework with window-like units and 2 shows a bimetallic structure. Nanocrystalline 1 and 2 were used as heterogeneous catalysts to study how adjacent catalytic active sites synergistically effected their catalytic reactivities in the direct catalytic conversion of aromatic dinitriles into oxazolines. The results showed that 1 produced bis-oxazolines as the sole products, whereas 2 gave the mono-oxazolines as the major products under the same reaction conditions.

An efficient oxidative conversion of aldehydes into 2-substituted 2-oxazolines using 1,3-diiodo-5,5-dimethylhydantoin

Various aromatic and aliphatic aldehydes were converted into the corresponding 2-aryl and 2-alkyl-2-oxazolines, respectively, in good to high yields by reaction with 2-aminoethanol and 1,3-diiodo-5,5-dimethylhydantoin. Moreover, chiral bis-2-oxazolines, which can be used as chiral ligands in asymmetric synthesis, could be also prepared in moderate yields by the reaction of dialdehydes with (R)-(-)-2-phenylglycinol under the same conditions. Georg Thieme Verlag Stuttgart.