131380-85-3

Basic information

• Product Name: Oxazole, 2,2'-(1,3-phenylene)bis[4,5-dihydro-4-(1-methylethyl)-, (4S,4'S)-
• CAS NO: 131380-85-3
• Molecular Formula: C18H24N2O2
• Molecular Weight: 300.401
• Mol File: 131380-85-3.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: Oxazole, 2,2'-(1,3-phenylene)bis[4,5-dihydro-4-(1-methylethyl)-, (4S,4'S)-(CAS DataBase Reference)
• NIST Chemistry Reference: Oxazole, 2,2'-(1,3-phenylene)bis[4,5-dihydro-4-(1-methylethyl)-, (4S,4'S)-(131380-85-3)
• EPA Substance Registry System: Oxazole, 2,2'-(1,3-phenylene)bis[4,5-dihydro-4-(1-methylethyl)-, (4S,4'S)-(131380-85-3)

Safety Data

• Hazardous Substances Data: 131380-85-3(Hazardous Substances Data)

Upstream product

• 626-17-5 benzene-1,3-dicarbonitrile 
• 2026-48-4 (S)-valinol 
• 121-91-5 isophthalic acid 
• 99-63-8 benzene-1,3-dicarbonyl dichloride 
• 475110-08-8 N¹,N³-bis((S)-1-hydroxy-3-methylbutan-2-yl)isophthalamide 

Relevant articles and documents

Phosphorus-Based Organocatalysis for the Dehydrative Cyclization of N-(2-Hydroxyethyl)amides into 2-Oxazolines

A metal-free, biomimetic catalytic protocol for the cyclization of N-(2-hydroxyethyl)amides to the corresponding 2-oxazolines (4,5-dihydrooxazoles), promoted by the 1,3,5,2,4,6-triazatriphosphorine (TAP)-derived organocatalyst tris(o-phenylenedioxy)cyclotriphosphazene (TAP-1) has been developed. This approach requires less precatalyst compared to the reported relevant systems, with respect to the phosphorus atom (the maximum turnover number (TON) ～30), and exhibits a broader substrate scope and higher functional-group tolerance, providing the functionalized 2-oxazolines with retention of the configuration at the C(4) stereogenic center of the 2-oxazolines. Widely accessible β-amino alcohols can be used in this approach, and the cyclization of N-(2-hydroxyethyl)amides provides the desired 2-oxazolines in up to 99% yield. The mechanism of the reaction was studied by monitoring the reaction using spectral and analytical methods, whereby an 18O-labeling experiment furnished valuable insights. The initial step involves a stoichiometric reaction between the substrate and TAP-1, which leads to the in situ generation of the catalyst, a catechol cyclic phosphate, as well as to a pyrocatechol phosphate and two possible active intermediates. The dehydrative cyclization was also successfully conducted on the gram scale.

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.

A facile and efficient synthesis of bis(oxazoline)s

Thiophene-2,5-dicarboxylic acid, benzene-1,3-dicarboxylic acid, or furan-2,5-di-carboxylic acid, respectively, reacted with various β-amino alcohols in toluene under reflux within 24 h, to form nine bis(oxazoline)s (1-3) in good yields through water deprivation via a one-pot reaction. The synthetic method is facile and efficient and deserves great application potentials in the research and development in the area of bis(oxazoline)s.