5839-93-0

Basic information

• Product Name: 4-ISOPROPYL-2-PHENYL-2-OXAZOLINE-5-ONE
• Synonyms: 4-ISOPROPYL-2-PHENYL-2-OXAZOLINE-5-ONE;4-ISOPROPYL-2-PHENYL-4H-OXAZOL-5-ONE;5(4H)-Oxazolone, 4-(1-methylethyl)-2-phenyl-;4-isopropyl-2-phenyloxazol-5(4H)-one;4-(1-Methylethyl)-2-phenyl-5(4H)-oxazolone
• CAS NO: 5839-93-0
• Molecular Formula: C₁₂H₁₃NO₂
• Molecular Weight: 203.24
• Mol File: 5839-93-0.mol
• Article Data: 36

Chemical Properties

• Melting Point: 41-45 °C
• Boiling Point: 281.9 °C at 760 mmHg
• Flash Point: 117.9 °C
• Appearance: /
• Density: 1.15 g/cm³
• Vapor Pressure: 0.00346mmHg at 25°C
• Refractive Index: 1.571
• PKA: 2.50±0.40(Predicted)
• CAS DataBase Reference: 4-ISOPROPYL-2-PHENYL-2-OXAZOLINE-5-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-ISOPROPYL-2-PHENYL-2-OXAZOLINE-5-ONE(5839-93-0)
• EPA Substance Registry System: 4-ISOPROPYL-2-PHENYL-2-OXAZOLINE-5-ONE(5839-93-0)

Safety Data

• Hazardous Substances Data: 5839-93-0(Hazardous Substances Data)

Usage

General Description

4-ISOPROPYL-2-PHENYL-2-OXAZOLINE-5-ONE is a chemical compound belonging to the oxazoline family. It is commonly used as a chiral building block in organic synthesis, particularly in the production of pharmaceuticals and agrochemicals. 4-ISOPROPYL-2-PHENYL-2-OXAZOLINE-5-ONE has unique stereochemical properties and is utilized as a versatile intermediate in asymmetric synthesis. It is known for its ability to form stable complexes with metal ions, making it useful in catalytic processes. Additionally, 4-ISOPROPYL-2-PHENYL-2-OXAZOLINE-5-ONE has applications in the production of specialty chemicals, polymers, and materials used in various industries.

InChI:InChI=1/C12H13NO2/c1-8(2)10-12(14)15-11(13-10)9-6-4-3-5-7-9/h3-8,10H,1-2H3

Upstream product

• 2901-80-6 N-benzoyl-D,L-valine 
• 98-88-4 benzoyl chloride 
• 28897-81-6 2-phenyl-4-iso-propyl-4H-oxazolin-5-one 
• 107-18-6 allyl alcohol 
• 2901-80-6 (2R)-2-(benzoylamino)-3-methylbutyric acid 
• 2901-80-6 N-benzoyl-L-valine 
• 541-41-3 chloroformic acid ethyl ester 
• 65-85-0 benzoic acid 
• 132353-23-2 2-(benzyloxy)-4,6-dimethoxy-1,3,5-triazin 
• 16975-39-6 2-(benzylamino)-3-methylbutanoic acid 
• 516-06-3 D,L-valine 
• 4491-47-8 2-phenyl-4-isopropylidene-5(4H)oxazolone 
• 108-24-7 acetic anhydride 

Downstream Products

• 70361-33-0 4-((E)-3,7-dimethyl-octa-2,6-dienyl)-4-isopropyl-2-phenyl-4H-oxazol-5-one 
• 70361-36-3 α-(4-Nitrobenzyl)valin 
• 55685-98-8 4-isopropyl-4-(2-nitro-benzyl)-2-phenyl-4H-oxazol-5-one 
• 55686-15-2 α-Benzylvalin 
• 55686-07-2 (4-isopropyl-5-oxo-2-phenyl-4,5-dihydro-oxazol-4-yl)-acetic acid ethyl ester 
• 21944-34-3 4-isopropyl-2-phenyloxazol-5-yl acetate 
• 55685-96-6 4-Allyl-4-(2-methylethyl)-2-phenyl-1,3-oxazol-5(4H)-on 
• 55686-14-1 4-isopropyl-2-phenyl-4-prop-2-ynyl-4H-oxazol-5-one 
• 34084-18-9 4-isopropyl-4-(3-oxo-3-phenyl-cis-propenyl)-2-phenyl-4H-oxazol-5-one 
• 34114-71-1 4-isopropyl-4-(3-oxo-3-phenyl-trans-propenyl)-2-phenyl-4H-oxazol-5-one 
• 55685-99-9 4-isopropyl-4-(2-oxo-2-phenyl-ethyl)-2-phenyl-4H-oxazol-5-one 
• 60050-43-3 2-(4-isopropyl-5-oxo-2-phenyl-4,5-dihydro-oxazol-4-yl)-propionic acid ethyl ester 
• 1492-13-3 (2R)-2-(benzoylamino)-3-methylbutyric acid methyl ester 
• 1492-13-3 N-benzoyl-L-valine methyl ester 

Relevant articles and documents

Base-catalysed 18F-labelling of trifluoromethyl ketones. Application to the synthesis of 18F-labelled neutrophil elastase inhibitors

A new method for the fluorine-18 labelling of trifluoromethyl ketones has been developed. This method is based on the conversion of a-COCF3 functional group to a difluoro enol silyl ether followed by halogenation and fluorine-18 labelling. The utility of this new method was demonstrated by the synthesis of fluorine-18 labelled neutrophil elastase inhibitors, which are potentially useful for detection of inflammatory disorders.

Metal-Free Insertion Reactions of Diazo Carbonyls to Azlactones

Insertion reactions of diazo carbonyls to azlactones in basic conditions have been performed. The developed method allows the preparation of a wide range of oxazole derivatives in yields ranging from 74 to 98%. Different substituents on both azlactone rings and diazo carbonyls do not compromise the methodology, even those containing stereogenic centers. Isotopic labeling experiments revealed the mechanism may proceed through a rare diazo carbonyl activation by an ammonium salt derivative.

One-Pot Vinylation of Azlactones: Fast Access to Enantioenriched α-Vinyl Quaternary Amino Acids

We report a fast one-pot protocol for the direct vinylation of azlactones [oxazol-5-(4H)-ones] by using as a key step an aldol addition with 2-(phenylselenenyl)acetaldehyde followed by dehydroxyselenation. The acid hydrolysis of the oxazolone ring gave the desired fully deprotected α-vinyl quaternary α-amino acids in almost quantitative yields. An enantioselective variant of the method was also developed by using catalytic chiral bases. The use of Sharpless ligand (DHQD)2PHAL produced the final quaternary amino acids in good overall yields (62–78 %) and with ee values up to 86 %. Scaling up the optimized protocol to gram quantities did not affect the yields and ee values. We also demonstrated that the vinyl moiety installed onto the oxazolone ring can be exploited as a handle for the attachment of aryl groups through a Heck coupling reaction.