1564-29-0

Basic information

• Product Name: 4-[4-(Dimethylamino)benzylidene]-2-phenyl-2-oxazolin-5-one
• Synonyms: 4-[4-(Dimethylamino)benzylidene]-2-phenyl-2-oxazolin-5-one;4-(4-Dimethylaminobenzyliden)-2-phenyloxazolone-5 (Luminore orange-red 612 T );LUMINORE ORANGE - RED 612 T;4-[(4-dimethylaminophenyl)methylidene]-2-phenyl-1,3-oxazol-5-one;2-Phenyl-4-[p-(dimethylamino)benzylidene]-2-oxazoline-5-one;4-[4-(Dimethylamino)benzylidene]-2-phenyloxazole-5(4H)-one;4-[p-(Dimethylamino)benzylidene]-2-phenyl-2-oxazolin-5-one;Orange Red II
• CAS NO: 1564-29-0
• Molecular Formula: C₁₈H₁₆N₂O₂
• Molecular Weight: 292.33184
• Product Categories: Piperazine derivates
• Mol File: 1564-29-0.mol
• Article Data: 59

Chemical Properties

• Melting Point: 216.5-217 °C
• Boiling Point: 451.7 °C at 760 mmHg
• Flash Point: 227 °C
• Appearance: /
• Density: 1.14 g/cm³
• Vapor Pressure: 2.37E-08mmHg at 25°C
• Refractive Index: 1.597
• PKA: 2.00±0.12(Predicted)
• CAS DataBase Reference: 4-[4-(Dimethylamino)benzylidene]-2-phenyl-2-oxazolin-5-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4-[4-(Dimethylamino)benzylidene]-2-phenyl-2-oxazolin-5-one(1564-29-0)
• EPA Substance Registry System: 4-[4-(Dimethylamino)benzylidene]-2-phenyl-2-oxazolin-5-one(1564-29-0)

Safety Data

• Hazardous Substances Data: 1564-29-0(Hazardous Substances Data)

Usage

Description

4-[4-(Dimethylamino)benzylidene]-2-phenyl-2-oxazolin-5-one is a synthetic oxazoline compound characterized by a complex chemical structure that includes a phenyl ring, a benzylidene group, and a dimethylamino group. This molecule is notable for its potential in chiral recognition due to the presence of the dimethylamino group, which makes it a promising candidate for chiral separation and analysis. Its unique structural features and properties position it as a valuable asset in the realms of organic synthesis, material development, and the creation of bioactive compounds, thus contributing significantly to chemical and pharmaceutical research.

Uses

Used in Organic Synthesis:
4-[4-(Dimethylamino)benzylidene]-2-phenyl-2-oxazolin-5-one is used as a key intermediate in organic synthesis for the development of new materials and bioactive compounds. Its unique structure allows for versatile chemical reactions, facilitating the creation of a wide range of organic molecules with potential applications in various industries.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 4-[4-(Dimethylamino)benzylidene]-2-phenyl-2-oxazolin-5-one is utilized as a chiral building block for the synthesis of enantiomerically pure drugs. Its ability to recognize chirality is crucial for the production of pharmaceuticals with specific biological activities, ensuring the desired therapeutic effects and minimizing side effects.
Used in Chiral Separation and Analysis:
4-[4-(Dimethylamino)benzylidene]-2-phenyl-2-oxazolin-5-one is employed as a chiral selector in chromatographic techniques for the separation of enantiomers. Its chiral recognition properties are instrumental in distinguishing between different stereoisomers of chiral compounds, which is essential for the purity and efficacy of pharmaceuticals and other chiral molecules.
Used in Material Science:
In the field of material science, 4-[4-(Dimethylamino)benzylidene]-2-phenyl-2-oxazolin-5-one is used as a component in the design and synthesis of advanced materials with specific properties. Its incorporation into polymers, for instance, can lead to materials with tailored characteristics such as improved stability, selectivity, or responsiveness to environmental stimuli.

InChI:InChI=1/C18H16N2O2/c1-20(2)15-10-8-13(9-11-15)12-16-18(21)22-17(19-16)14-6-4-3-5-7-14/h3-12H,1-2H3/b16-12+

Upstream product

• 14848-36-3 4-chloromethylene-2-phenyl-4H-oxazol-5-one 
• 121-69-7 N,N-dimethyl-aniline 
• 15646-46-5 4-ethoxymethylene-2-phenyl-2-oxazolin-5-one 
• 495-69-2 Hippuric Acid 
• 108-24-7 acetic anhydride 
• 100-10-7 4-dimethylamino-benzaldehyde 
• 1199-01-5 2-phenylazlactone 
• 889-37-2 N,N-dimethyl-4-((phenylimino)methyl)aniline 
• 101306-91-6 sodium 1-hydroxy-1-(4-dimethylaminophenyl)methanesulfonate 
• 532-94-5 sodium hippurate 
• 65-85-0 benzoic acid 
• 98-88-4 benzoyl chloride 
• 104-87-0 4-methyl-benzaldehyde 
• 103-72-0 phenyl isothiocyanate 

Downstream Products

• 119888-26-5 α-benzoylamino-4-dimethylamino-trans-cinnamic acid 
• 141212-43-3 (Z)-2-amino-4-p-dimethylaminobenzylidene-2-imidazolin-5-one 
• 144809-96-1 N-[(5S,6S)-6-(4-Dimethylamino-phenyl)-4-oxo-2-thioxo-3-o-tolyl-[1,3]thiazinan-5-yl]-benzamide 
• 144809-95-0 N-[(5R,6R)-6-(4-Dimethylamino-phenyl)-4-oxo-3-phenyl-2-thioxo-[1,3]thiazinan-5-yl]-benzamide 
• 144809-97-2 N-[(5S,6S)-6-(4-Dimethylamino-phenyl)-3-naphthalen-1-yl-4-oxo-2-thioxo-[1,3]thiazinan-5-yl]-benzamide 
• 144810-00-4 Naphthalen-1-yl-dithiocarbamic acid (R)-(4-dimethylamino-phenyl)-((R)-5-oxo-2-phenyl-4,5-dihydro-oxazol-4-yl)-methyl ester 
• 107399-72-4 (Z)-4-(4-(dimethylamino)benzylidene)-1,2-diphenyl-1H-imidazol-5(4H)-one 
• 99855-77-3 (4-(N,N-dimethylamino)phenyl)pyruvic acid 
• 1352220-98-4 N-{(Z)-1-(methylcarbamoyl)-2-[4-(dimethylamino)phenyl]vinyl}benzamide 
• 1352221-02-3 N-[(Z)-1-(cyclopropylcarbamoyl)-2-(4-(dimethylamino)phenyl)vinyl]benzamide 
• 136712-96-4 3-(Benzothiazol-2-ylamino)-5-[1-(4-dimethylamino-phenyl)-meth-(Z)-ylidene]-2-phenyl-3,5-dihydro-imidazol-4-one 
• 1187940-69-7 C₂₆H₃₃N₂O₇P 
• 13895-51-7 ethyl-2-(benzoylamino)-3-[4-(dimethylamino)-phenyl]acrylate 
• 1246511-72-7 C₂₄H₂₁N₅O₂ 

Relevant articles and documents

Synthesis and luminescence properties of analogues of the green fluorescent protein chromophore

The green fluorescent protein (GFP) is extensively used as a biomarker for fluorescence biological imaging. The chromophore in GFP is only fluorescent when confined into the β–barrel of the protein. Similarly, synthetic analogues of the fluorophore of GFP

Benzothiazol clubbed imidazol-4-ones as anti-fungal, anti-tubercular and anti-HIV-1 agents: Their synthesis and molecular docking study

Background: The present work describes antimicrobial, antimycobacterium and anti HIV-1 evaluation of newly synthesized 5-(4-Substituted-benzylidene)-3-[4-(5-methyl-benzothiazol2-yl)-phenyl]-2-phenyl-3,5-dihydro-imidazol-4-one (4a-o). The docking studies were performed in order to predict the potential binding affinities. Objective: The major aim of this study is to develop the new class of bezylidine candidate clubbed with benzothiazole with less toxicity and improved potency as antimicrobial, antitubercular and anti HIV-1. Methods: The titled compounds were characterized by spectral studies (IR, 1H NMR, 13C NMR and Mass). In vitro antimycobacterium activity was carried out using Lowenstein-Jensen medium method and antimicrobial activity using the broth microdilution method. The anti HIV-1 reverse transcriptase activity was determined by the colorimetric MTT method and inhibition of virusinduced cytopathogenicity in MT-4 cells. Results: Compound 4i (50 μM) showed better antifungal activity against A. clavatus. Compound 4g (50 μM) with 95% inhibition demonstrated good activity against M. tuberculosis H37Rv. Compound 4k showed CC50 (50 μM) against MT-4 (CD4+ Human T-cells containing an integrated HTLV-1 genome) cells by 50%, while 16 μM concentration value EC50 from the HIV-1 induced cytopathogenicity. Molecular docking study suggested that 4k interacted with the target with binding energy by Vina score (-10.3 Kcal/mol) Conclusion: The preliminary in vitro evaluation results revealed that some of the compounds have promising antimicrobial activities as well as antitubercular potency. Among the various substituents on benzylidene, the nitro group was the most beneficial for improving the anti-HIV-1 activity. Docking result suggested that 4k compound could be acting as a non-competitive or weak inhibitor of Reverse Transcriptase (RT).

An ionic liquid gel: A heterogeneous catalyst for Erlenmeyer-Plochl and Henry reactions

An ionic liquid gel has been prepared by entrapping 1-butyl-3-methylimidazolium hydroxide ([Bmim]OH) in an aqueous agar gel. The ionic liquid gel has been characterized by Fourier transform infrared (FT-IR), Fourier transform Raman (FT-Raman) spectroscopy, scanning electron microscopy (SEM), thermogravimetric analysis (TGA) and energy dispersive X-ray analysis (EDX). The ionic liquid gel has been successfully employed as a heterogeneous catalyst in the Erlenmeyer-Plochl reaction involving aldehydes, hippuric acid and acetic anhydride as well as in the Henry reaction between aldehydes and nitromethane in ethanol at room temperature. The heterogeneity of the ionic liquid gel has been confirmed by conducting hot filtration tests and leaching studies. Additionally, the ionic liquid gel could be easily recovered by simple filtration and reused five times without significant loss in catalytic activity.