565455-78-9

Basic information

• Product Name: Oxazole, 2-(4-chlorophenyl)-4,5-dihydro-4-(1-methylethyl)-, (4S)-
• CAS NO: 565455-78-9
• Molecular Formula: C12H14ClNO
• Molecular Weight: 223.702
• Mol File: 565455-78-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Oxazole, 2-(4-chlorophenyl)-4,5-dihydro-4-(1-methylethyl)-, (4S)-(CAS DataBase Reference)
• NIST Chemistry Reference: Oxazole, 2-(4-chlorophenyl)-4,5-dihydro-4-(1-methylethyl)-, (4S)-(565455-78-9)
• EPA Substance Registry System: Oxazole, 2-(4-chlorophenyl)-4,5-dihydro-4-(1-methylethyl)-, (4S)-(565455-78-9)

Safety Data

• Hazardous Substances Data: 565455-78-9(Hazardous Substances Data)

Upstream product

• 2026-48-4 (S)-valinol 
• 74-11-3 para-chlorobenzoic acid 
• 623-03-0 4-Cyanochlorobenzene 
• 122-01-0 4-chloro-benzoyl chloride 
• 565455-79-0 (S)-4-chloro-N-(1-hydroxy-3-methylbutan-2-yl)benzamide 

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.

Hammett studies of enantiocontrol by PHOX ligands in Pd-catalyzed allylic substitution reactions

(Matrix presented) Electronically modified PHOX ligands 3a-e were synthesized to probe the mechanism of the enantioselective palladium-catalyzed allylic alkylation and amination reactions. Alkylation with dimethyl sodiomalonate produced only a small variation in the ee (89.3% to 93.4%), but amination with benzylamine gave a much wider variation in the ee (16.4% to 66.6%). Hammett analysis suggests that the substituents interact more significantly with phosphorus and supports a combined electronic and steric basis for enantioselection.