15646-46-5

Basic information

• Product Name: 4-ETHOXYMETHYLENE-2-PHENYL-2-OXAZOLIN-5-ONE
• Synonyms: 4-ETHOXYMETHYLENE-2-PHENYL-2-OXAZOLIN-5-ONE;4-ETHOXYMETHYLENE-2-PHENYLOXAZOLIN-5-ONE;4-ETHOXYMETHYLENE-2-PHENYLOXAZOLINE-5-ONE;AKOS BBS-00001130;OXAZOLONE SENSITIZING AGENT;4-(ethoxymethylene)-2-phenyl-5(4h)-oxazolon;4-ethoxymethylene-2-phenyl-2-oxazolin-5-on;4-ETHOXYMETHYLEN-2-PHENYL-2-OXAZOLIN-5-O
• CAS NO: 15646-46-5
• Molecular Formula: C₁₂H₁₁NO₃
• Molecular Weight: 217.22
• EINECS: 239-713-9
• Product Categories: API intermediates;Building Blocks;Heterocyclic Building Blocks;Oxazolines/Oxazolidines
• Mol File: 15646-46-5.mol
• Article Data: 11

Chemical Properties

• Melting Point: 94-96 °C (dec.)(lit.)
• Boiling Point: 357.77°C (rough estimate)
• Flash Point: 136.8 °C
• Appearance: White to orange or pink powder
• Density: 1.2160 (rough estimate)
• Vapor Pressure: 0.000666mmHg at 25°C
• Refractive Index: 1.5560 (estimate)
• Storage Temp.: 2-8°C
• PKA: -2.59±0.20(Predicted)
• Water Solubility: Soluble in methanol (50 mg/ml), and water (partly).
• BRN: 163055
• CAS DataBase Reference: 4-ETHOXYMETHYLENE-2-PHENYL-2-OXAZOLIN-5-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-ETHOXYMETHYLENE-2-PHENYL-2-OXAZOLIN-5-ONE(15646-46-5)
• EPA Substance Registry System: 4-ETHOXYMETHYLENE-2-PHENYL-2-OXAZOLIN-5-ONE(15646-46-5)

Safety Data

• Hazard Codes: Xn
• Statements: 43
• Safety Statements: 36
• WGK Germany: 3
• RTECS: RQ5786250
• HazardClass: IRRITANT
• Hazardous Substances Data: 15646-46-5(Hazardous Substances Data)

Usage

Chemical Properties

white to orange or pink powder

Uses

Different sources of media describe the Uses of 15646-46-5 differently. You can refer to the following data:
1. 4-Ethoxymethylene-2-phenyloxazolin-5-one acts as sensitizing agent. It is also used as pharmaceutical intermediates.
2. 4-Ethoxymethylene-2-phenyl-2-oxazolin-5-one has been used as a haptenizing agent, which can induce an inflammatory reaction in adult zebrafish intestinal tissues and this can be used as a model for gene expression studies of the two forms of inflammatory bowel disease like Crohn′s disease and ulcerative colitis.

Definition

ChEBI: A 1,3-oxazole compound having a phenyl substituent at the 2-position, an ethoxymethylene group at the 4-position, and an oxo group at the 5-position. It is a chemical allergen used for immunological experiments, particularly for experiments on delayed typ hypersensitivity.

InChI:InChI=1/C12H11NO3/c1-2-15-8-10-12(14)16-11(13-10)9-6-4-3-5-7-9/h3-8H,2H2,1H3/b10-8-

Synthetic route

Hippuric Acid (495-69-2) + orthoformic acid triethyl ester (122-51-0) → 4-ethoxymethylene-2-phenyl-2-oxazolin-5-one (15646-46-5)

Conditions	Yield
With acetic anhydride at 140℃; for 1h;	70%
In tetrahydrofuran; acetic anhydride for 0.75h; Inert atmosphere; Reflux;	45%
With acetic anhydride for 0.5h; Heating;	34%

Upstream product

• 495-69-2 Hippuric Acid 
• 122-51-0 orthoformic acid triethyl ester 
• 1199-01-5 2-phenylazlactone 
• 123-54-6 acetylacetone 
• 109-94-4 formic acid ethyl ester 
• 719302-55-3 3,3-diethoxy-2-benzoylamino-propionic acid 
• 120165-75-5 3-ethoxy-2-benzoylamino-acrylic acid 
• 345894-39-5 4-methoxymethylene-2-phenyl-4H-oxazol-5-one 

Downstream Products

• 92579-87-8 2-phenyl-4-piperidin-1-ylmethylene-4H-oxazol-5-one 
• 42136-84-5 for 3e 
• 94067-79-5 4-(2-methyl-3-piperidin-1-yl-allylidene)-2-phenyl-4H-oxazol-5-one 
• 78650-35-8 6-Benzoylamino-4-oxo-5H-thiazolo<2,3-b>pyrimidine 
• 78666-78-1 2-phenyl-4-(2-thiazolylaminomethylene)-2-oxazolin-5-one 
• 215545-72-5 4-benzoylhydrazinomethylene-2-phenyloxazol-5(4H)-one 
• 1391158-45-4 C₂₃H₂₂FN₃O₄ 
• 634148-47-3 5-(benzoylamino)-6-oxo-2-phenyl-1(6H)-pyrimidineacetic acid tert-butyl ester 
• 1253654-20-4 N-{2-[(4-methylbenzyl)sulfanyl]-6-oxo-1,6-dihydropyrimidin-5-yl}benzamide 
• 109315-25-5 N-[2-(benzylsulfanyl)-6-oxo-1,6-dihydropyrimidin-5-yl]benzamide 
• 1253654-16-8 N-{2-[(4-chlorobenzyl)sulfanyl]-6-oxo-1,6-dihydropyrimidin-5-yl}benzamide 
• 1253654-18-0 N-{2-[(4-bromobenzyl)sulfanyl]-6-oxo-1,6-dihydropyrimidin-5-yl}benzamide 
• 1253654-14-6 N-{2-[(3-chlorobenzyl)sulfanyl]-6-oxo-1,6-dihydropyrimidin-5-yl}benzamide 
• 1253654-12-4 N-{2-[(2-chlorobenzyl)sulfanyl]-6-oxo-1,6-dihydropyrimidin-5-yl}benzamide 

Relevant articles and documents

Reaction of 2-phenyl-4-(ethoxymethylene)-5(4H)-oxazolone with 3,4-dithio-toluene in the presence of Lewis base

A convenient procedure for the synthesis of thiocoumarin by the condensation of 2-phenyl-4-(ethoxymethylene)-5-(4H)-oxazolone with 3,4-dithio-toluene in the presence of triethylamine is reported. Here, both thio groups are able to react with the carbonyl group to produce a mixture of isomeric products at ambient temperature. Only one of the isomers upon heating gives a new coumarin product.

Palladium-catalyzed diastereo- and enantioselective formal [3 + 2]-cycloadditions of substituted vinylcyclopropanes

We describe a palladium-catalyzed diastereo- and enantioselective formal [3 + 2]-cycloaddition between substituted vinylcyclopropanes and electron-deficient olefins in the form of azlactone- and Meldrums acid alkylidenes to give highly substituted cyclopentane products. By modulation of the electronic properties of the vinylcyclopropane and the electron-deficient olefin, high levels of stereoselectivity were obtained. The remote stereoinduction afforded by the catalyst, distal from the chiral pocket generated by the ligand, is proposed to be the result of a new mechanism invoking the Curtin-Hammett principle.

Syntheses of 5-amino-2-phenyl-4(3H)-pyrimidinone derivertives starting with glycine

N-Cbz derivative of 5-amino-2-phenyl-4(3H)-pyrimidinone was prepared from sodium salt of methyl hydroxymethylene glycinate and benzamidine hydrochloride in good yield. However, the reaction with N-substituted benzamidine did not proceed to give the desired pyrimidinone. In contrast, the reaction of 4-ethoxymethylene-2-phenyl-5(4H)-oxazolone readily prepared from hippuric acid and N-substituted benzamidine proceeded nicely to give 5-(benzoylamino)-6-oxo-2- phenyl-1(6H)-pyrimidineacetic acid in high yield.