118949-61-4

Basic information

• Product Name: (S,S)-2,6-BIS(4-ISOPROPYL-2-OXAZOLIN-2-YL)PYRIDINE
• Synonyms: 2,6-Bis[(4S)-4-isopropyl-2-oxazolin-2-yl]pyridine;2,6-Bis((S);-4-isopropyl-4,5-dihydrooxazol-2-yl);2,6-Bis[(4S)-isopropyl-2-oxazolin-2-yl]pyridine,99%e.e.;(-)-2,6-BIS[(4S)-4-(I-PROPYL)-2-OXAZOLIN-2-YL]PYRIDINE;2,6-BIS[(4S)-(-)-ISOPROPYL-2-OXAZOLIN-2-YL]PYRIDINE;(S,S)-2,2'-(2,6-PYRIDINEDIYL)BIS(4-ISOPROPYL-2-OXAZOLINE);(S,S)-2,6-BIS(4-ISOPROPYL-2-OXAZOLIN-2-YL)PYRIDINE
• CAS NO: 118949-61-4
• Molecular Formula: C₁₇H₂₃N₃O₂
• Molecular Weight: 301.38
• Product Categories: BOX series;Chiral Nitrogen;Asymmetric Synthesis;Synthetic Organic Chemistry;organic amine
• Mol File: 118949-61-4.mol
• Article Data: 11

Chemical Properties

• Melting Point: 155-157 °C(lit.)
• Boiling Point: 457.1 °C at 760mmHg
• Flash Point: 230.2 °C
• Appearance: white/crystal
• Density: 1.23 g/cm³
• Vapor Pressure: 4.18E-08mmHg at 25°C
• Refractive Index: 1.607
• Storage Temp.: Refrigerator
• PKA: 3.78±0.70(Predicted)
• BRN: 5824976
• CAS DataBase Reference: (S,S)-2,6-BIS(4-ISOPROPYL-2-OXAZOLIN-2-YL)PYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: (S,S)-2,6-BIS(4-ISOPROPYL-2-OXAZOLIN-2-YL)PYRIDINE(118949-61-4)
• EPA Substance Registry System: (S,S)-2,6-BIS(4-ISOPROPYL-2-OXAZOLIN-2-YL)PYRIDINE(118949-61-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 118949-61-4(Hazardous Substances Data)

Usage

Description

(S,S)-2,6-BIS(4-ISOPROPYL-2-OXAZOLIN-2-YL)PYRIDINE is a chiral ligand characterized by its white powder, crystal, or chunk form. It features a pyridine core with two 4-isopropyl-2-oxazolinyl groups attached at the 2,6 positions, which contribute to its unique chemical properties and potential applications in various fields.

Uses

Used in Catalyst Preparation:
(S,S)-2,6-BIS(4-ISOPROPYL-2-OXAZOLIN-2-YL)PYRIDINE is used as a ligand for the preparation of novel ruthenium-pyridine-carboxylate complexes. These complexes serve as new catalytic systems for alkene epoxidation, a significant reaction in organic chemistry for the synthesis of various chemical compounds and pharmaceuticals.
Used in Chemical Synthesis Industry:
In the chemical synthesis industry, (S,S)-2,6-BIS(4-ISOPROPYL-2-OXAZOLIN-2-YL)PYRIDINE is utilized as a chiral ligand to create enantioselective catalysts. These catalysts are essential for the production of enantiomerically pure compounds, which are crucial in pharmaceuticals, agrochemicals, and other specialty chemicals where the stereochemistry of a molecule can significantly impact its biological activity and efficacy.
Used in Research and Development:
(S,S)-2,6-BIS(4-ISOPROPYL-2-OXAZOLIN-2-YL)PYRIDINE is also used in research and development settings to explore its potential applications in asymmetric catalysis, enantioselective synthesis, and other areas of organic chemistry. Its unique structural features make it a valuable tool for chemists to study and develop new reactions and processes that can lead to innovative products and technologies.

Reaction

Ligand used in the dual-catalyst system for highly enantioselective conjugate cyanation of unsaturated imides. Ligand for cross-coupling reactions of iodoalkanes with alkyl zinc halides. Ligand for asymmetric 1,4-addition reactions of 1,3-dicarbonyl compounds to nitroalkenes. Ligand for asymmetric allylation of aldehydes with b-carbonyl allylstannanes. Ligand used in the enantioselective Negishi reaction of racemic secondary benzylic halides. Ligand for osmium catalyzed enantioselective transfer hydrogenation.

InChI:InChI=1/C17H23N3O2/c1-10(2)14-8-21-16(19-14)12-6-5-7-13(18-12)17-20-15(9-22-17)11(3)4/h5-7,10-11,14-15H,8-9H2,1-4H3/t14-,15-/m1/s1

Upstream product

• 2893-33-6 pyridine-2,6-dinitrile 
• 2026-48-4 (S)-valinol 
• 329038-95-1 Pyridine-2,6-dicarboxylic acid bis-[((S)-1-chloromethyl-2-methyl-propyl)-amide] 
• 329038-94-0 N²,N⁶-bis((S)-1-hydroxy-3-methylbutan-2-yl)pyridine-2,6-dicarboxamide 
• 5431-44-7 2,6-Pyridinedicarboxaldehyde 
• 3739-94-4 2,6-Pyridinedicarbonyl dichloride 
• 499-83-2 Pyridine-2,6-dicarboxylic acid 
• 55309-58-5 pyridine-2,6-dicarboximidic acid dimethyl ester 
• 626-05-1 2,6-Dibromopyridine 
• 132376-99-9 (S)-4-isopropyl-4,5-dihydrooxazole 

Relevant articles and documents

Steric versus electronic effects of the ligand in the enantioselective palladium-catalyzed allylic alkylation with chiral oxazolinylpyridines

Chiral oxazolinylpyridines bearing an oxazolinyl [bis(oxazolinyl)pyridines] or a cyano group in the 6-position of the pyridine ring were prepared and assessed in the enantioselective palladium-catalyzed allylic substitution of 1,3-diphenylprop-2-enyl acet

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

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.

Synthesis, characterization and 1,3-butadiene polymerization studies of cobalt dichloride complexes bearing pyridine bisoxazoline ligands

A series of ion-pair cobalt complexes bearing pyridine bisoxazoline ligands were successfully synthesized and characterized by IR spectroscopy and elemental analysis. Determined by X-ray crystallographic analysis, complexes 4a, 4b, 4e, and 4f existed as i