1199-01-5

Basic information

• Product Name: 2-PHENYL-5-OXAZOLONE
• Synonyms: 2-phenyl-5(4h)-oxazolon;2-phenyloxazolone;2-PHENYL-5-OXAZOLONE;2-PHENYL-4H-OXAZOL-5-ONE ;2-PHENYL-2-OXAZOLIN-5-ONE;2-Phenyl-2-oxazoline-5-one;2-Phenyl-5(4H)-oxazolone;Phenyloxazolone
• CAS NO: 1199-01-5
• Molecular Formula: C₉H₇NO₂
• Molecular Weight: 161.16
• EINECS: 214-840-2
• Mol File: 1199-01-5.mol

Chemical Properties

• Melting Point: 89-92°C
• Boiling Point: 248.1 °C at 760 mmHg
• Flash Point: 117.8 °C
• Appearance: /
• Density: 1.25 g/cm³
• Vapor Pressure: 3.3E-05mmHg at 25°C
• Refractive Index: 1.548
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Soluble in most common organic solvents.
• PKA: 2.56±0.20(Predicted)
• Sensitive: Air Sensitive
• BRN: 128465
• CAS DataBase Reference: 2-PHENYL-5-OXAZOLONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-PHENYL-5-OXAZOLONE(1199-01-5)
• EPA Substance Registry System: 2-PHENYL-5-OXAZOLONE(1199-01-5)

Safety Data

• Safety Statements: 22-24/25
• TSCA: Yes
• Hazardous Substances Data: 1199-01-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Phenyl-5-oxazolone is used as a reagent for the synthesis of various heterocyclic compounds, which are essential in the development of new pharmaceuticals. Its ability to act as a masked glycine equivalent allows for the creation of complex molecular structures that can be used as potential drug candidates.
Used in Chemical Research:
In the field of chemical research, 2-Phenyl-5-oxazolone is employed as a key building block for the formation of heterocyclic structures. These structures are vital in the study and development of novel chemical compounds with potential applications in various industries, including materials science, agrochemicals, and pharmaceuticals.
Used in Material Science:
2-Phenyl-5-oxazolone can be used as a component in the development of new materials with specific properties, such as improved stability, reactivity, or selectivity. These materials can be applied in various industries, including electronics, coatings, and adhesives.
Used in Agrochemicals:
In the agrochemical industry, 2-Phenyl-5-oxazolone can be utilized in the synthesis of novel compounds with potential applications as pesticides, herbicides, or fungicides. These compounds can help improve crop protection and yield, contributing to sustainable agriculture practices.
Overall, 2-Phenyl-5-oxazolone is a versatile compound with applications in various industries, including pharmaceuticals, chemical research, material science, and agrochemicals. Its unique properties and reactivity make it a valuable tool for the development of new compounds and materials with potential benefits in these fields.

InChI:InChI=1/C9H9NO2/c11-8-6-10-9(12-8)7-4-2-1-3-5-7/h1-5,9-10H,6H2

Upstream product

• 495-69-2 Hippuric Acid 
• 108-24-7 acetic anhydride 
• 2979-54-6 phenyl hippurate 
• 29736-20-7 Benzoylamino-acetic acid p-tolyl ester 
• 66895-70-3 Benzoylamino-acetic acid m-tolyl ester 
• 66895-69-0 Benzoylamino-acetic acid o-tolyl ester 
• 2979-52-4 hippuric acid 4-chlorophenyl ester 
• 2979-53-5 3-nitrophenyl hippurate 
• 29736-21-8 4-Methoxyphenylhippurat 
• 29736-18-3 4-Acetylphenylhippurat 
• 57461-26-4 Benzoylamino-acetic acid 3-chloro-phenyl ester 
• 541-41-3 chloroformic acid ethyl ester 
• 102741-67-3 Benzoylamino-acetic acid 2-chloro-phenyl ester 
• 102741-58-2 Benzoylamino-acetic acid 2,3-dimethyl-phenyl ester 

Downstream Products

• 17606-70-1 (4Z)-4-benzylidene-2-phenyl-1,3-oxazol-5(4H)-one 
• 22747-91-7 1-benzoyl-3-benzoylamino-pyrrolidine-2,4-dione 
• 77012-48-7 2-phenyl-4-(2-furylmethylidene)-2-oxazolin-5-one 
• 105402-18-4 1-hippuroyl-3-methyl-1,3-dihydro-imidazole-2-thione 
• 5438-08-4 4-trans-cinnamylidene-2-phenyl-4H-oxazol-5-one 
• 21286-78-2 methyl N-benzoyl-2-methoxyglycinate 
• 6664-97-7 hippuroyloxy-acetic acid 
• 84797-84-2 2-phenyl-4-phenylhydrazono-2-oxazolin-5-one 
• 84719-24-4 2-phenyl-oxazole-4,5-dione-4-(4-nitro-phenylhydrazone) 
• 24639-11-0 N-hippuroyl-alanine 
• 4703-39-3 N-hippuroyl-3-phenyl-alanine 
• 117123-84-9 hippuric acid-[5-(4-nitro-phenoxy)-pentylamide] 
• 85094-77-5 2-phenyl-4-propionyl-5-oxazolinone 
• 52956-46-4 4-cyclohexylidene-2-phenyloxazol-5(4H)-one 

Relevant articles and documents

Structures of b and a product ions from the fragmentation of argentinated peptides

Argentinated (silver-containing) oligopeptides fragment under low- energy collision conditions to yield abundant argentinated product ions. The structures of the [b2 - H + Ag]+ and [a2 - H + Ag]+ ions have been determined by means of tandem mass spectrometry and confirmed by comparison with synthesized derivatives of the candidate [b2 - H + Ag]+ ion structure. The [b2 - H + Ag]+ ion was found to be an N-argentinated oxazolone, which could subsequently form the [a2 - H + Ag]+ ion and other product ions after collision activation. Tripeptides containing proline as their second residue were observed to form a relatively less abundant [b2 - H + Ag]+ ion, which was postulated to be an argentinated ketene.

4-Phosphoranylidene-5(4H)-oxazolones - A Novel Synthesis and Properties

4-Phosphoranylidene-5(4H)-oxazolones (2), a hardly known class of phosphorus ylides, were readily prepared from 4-unsubstituted-5-(4H)-oxazolones (1) by treatment with Ph3P-Br2, Bu3P-Br2, Ph3P-CCl4, or Ph3P-CBr4 adducts in the presence of triethylamine in CH2Cl2 at room temperature in a novel, efficient one-pot procedure. The spectroscopic properties of the ylides are reported and discussed.

Room-Temperature Dual Fluorescence of a Locked Green Fluorescent Protein Chromophore Analogue

A structurally locked green fluorescent protein (GFP) chromophore with a phenyl group at C(2) of the imidazolone has been synthesized. Rotation around the exocyclic double bond is hindered, resulting in room-temperature fluorescence. The quantum yield in water is 500 times greater than that of unlocked analogues. Unlike the methyl-substituted analogue, the phenyl analogue exhibits a dual emission (cyan and red) that can be used for ultrasensitive ratiometric measurements and fluorescence microscopy. To explain this dual emission, DFT calculations were carried out along with fluorescence upconversion experiments. The Z-isomer was found to be emissive, while the origin of the dual emission was dependent on the phenyl group in the Z-isomer, which stabilizes the Franck-Condon state, resulting in a cyan fluorescence, while the zwitterionic tautomer fluoresces red. These results bring important new insights into the photophysics of the GFP chromophore and provide a new scaffold capable of dual emission with utility in biotechnology.

Transformation of arylcarboxamides into 1,3-dioxo-1,3-dihydroisobenzofuran-4-carboxamides: Dedicated to Professor Emeritus Dr. Miha Ti?ler on the occasion of his 90th birthday

In this paper, we describe a four step synthesis of 1,3-dioxo-1,3-dihydroisobenzofuran-4-carboxamides starting from (hetero)arylcarboxamides. These are first transformed to the corresponding acetamidines followed by condensation to substituted [(oxazol-4(5H)-ylidene)ethyl]benzamides, which are further derivatized to substituted [(oxazol-4(5H)-ylidene)allyl]benzamides. The latter compounds undergo a supposed [4 + 2] cycloaddition with maleic anhydride, leading to the final products.

Reaction of 4-benzylidene-2-phenyloxazol-5(4H)-one with 3,4- dithio-toluene in the presece of triethylamine

Unsaturated oxazol-5(4H)-ones constitute an important class of synthon. In this paper we present our findings on the reaction of 4-benzylidene-2- phenyloxazol-5(4H)-one and 4-cyclohexylidene-2-phenyloxazol-5(4H)-one and 4-cyclohexylidene-2-phenyloxazol-5(4H)-one with 3,4-dithio-toluene in the presence of triethylamine. The intermediates can be isolated under nautral conditions. Base mediated reaction of 3,4-dithio toluene with 4-benzylidene-2-phenyloxazol-5(4H)-one in boiling benzene was unsuccessful but simple heating of these reactants at an elevated temperature give 2-benzamido-2-cyclohexyl-7-methyl-1,4-benzodithian-3-one.

Simple and efficient multigram scale synthesis of 1-aminocyclopent-3-ene-1- carboxylic acid

A very simple and inexpensive synthesis of the valuable intermediate 1-aminocyclopent-3-ene-1-carboxylic acid on a multigram scale and with a high overall yield (80%) is reported. The efficiency of the procedure relies on the ready accessibility and high reactivity of the glycine equivalent used as the starting material. Georg Thieme Verlag Stuttgart.

Synthesis, cytotoxicity, and docking study of novel 1-naphthyl-5-aryl-1H-1,2,4-triazole-3-carboxamides

A new series of 1-naphthyl-5-aryl-1H-1,2,4-triazole-3-carboxamide derivatives were synthesized and structurally proved by 1H and 13C NMR along with high-resolution mass spectrometry. The cytotoxic activity of the newly synthesized compounds was evaluated. Compounds showed a pronounced inhibitory effect against cellular localization of tubulin. Flow cytometric analysis showed that Hep-G2 cells treated indicated a predominated growth arrest at the G2/M-phase compared to that of S-phase. Molecular modeling study using MOE program indicated that most of the target compounds showed good binding with the colchicine-binding site of β-subunit of tubulin with the binding free energy (?G) values of about 42?kJ/mol. Graphical abstract: [Figure not available: see fulltext.].

Synthesis and antimicrobial evaluation of the novel heteroannulated furo[3′,2′:6,7]chromeno[2,3-b]pyridines: Part 1

The chemical behavior of 4,9-dimethoxy-5-oxo-5H-furo[3,2-g]chromene-6-carbonitrile (1) was investigated toward some acyclic and cyclic active methylene ketones namely acetylacetone, ethyl acetoacetate, ethyl benzoylacetate, acetoacetanilide, dimedone, indanedione, pyrazolidine-3,5-dione and 5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one, barbituric acid and 1-allylthiobarbituric acid, and hippuric acid. A variety of novel heteroannulated furochromenopyridines were efficiently synthesized through a cascade reactions between 4,9-dimethoxy-5-oxo-5H-furo[3,2-g]chromene-6-carbonitrile (1) and the carbon nucleophilic reagents. Structures of the new products were inferred based on their analytical and spectral data.

An eco-compatible access to diversified bisoxazolone and bisimidazole derivatives

An efficient, straight-forward and eco-friendly synthetic strategy for the assembly of novel bisoxazolones via a four-component, sequential reaction of dialdehydes, glycine, benzoyl chloride and acetic anhydride, using ultrasound radiation, is described. Additionally, a diverse group of new bisimidazoles has been synthesized in good yields by the sonication of diamines and (Z)-4-Arylidene-2-phenyloxazol-5(4H)-ones. These approaches have resulted in a number of successful routes for the facile synthesis of bis-oxazolone and bis-imidazole frameworks within minutes of irradiation. Excellent outcomes using these environmentally-friendly parameters make these synthetic schemes ideal, sustainable, green-chemistry procedures and provide simple access towards the preparation of bisheterocycles. Formula parented.

Microwave activated solvent-free cascade reactions yielding highly functionalised 1,3-thiazines

One-pot cascade reactions of N-acylglycines, acetic anhydride, anhydrous sodium acetate, aromatic aldehydes, and ammonium N-aryldithiocarbamates expeditiously and diastereoselectively yield 5-acylamino-3,6-diarylperhydro-2-thioxo-1,3-thiazin-4-ones (5a-j) in solvent-free conditions under microwave irradiation.