81428-58-2

Basic information

• Product Name: phenol oxazoline
• Synonyms: phenol oxazoline;4-(4,5-DIHYDRO-2-OXAZOLYL)-PHENOL
• CAS NO: 81428-58-2
• Molecular Formula: C₉H₉NO₂
• Molecular Weight: 163.17326
• Mol File: 81428-58-2.mol

Chemical Properties

• Boiling Point: 279°Cat760mmHg
• Flash Point: 122.5°C
• Appearance: /
• Density: 1.272g/cm³
• Vapor Pressure: 0.00413mmHg at 25°C
• Refractive Index: 1.592
• CAS DataBase Reference: phenol oxazoline(CAS DataBase Reference)
• NIST Chemistry Reference: phenol oxazoline(81428-58-2)
• EPA Substance Registry System: phenol oxazoline(81428-58-2)

Safety Data

• Hazardous Substances Data: 81428-58-2(Hazardous Substances Data)

Usage

Uses

Used in Coordination Chemistry:
Phenol oxazoline is used as a ligand for forming stable complexes with metal ions, which is crucial in coordination chemistry. Its ability to bind with metals allows for the study of metal-ligand interactions and the development of new compounds.
Used in the Production of Plastics, Resins, and Adhesives:
Phenol oxazoline is utilized as a component in the manufacturing process of plastics, resins, and adhesives. Its properties contribute to the overall performance and stability of these materials.
Used in Catalysis:
Phenol oxazoline serves as a catalyst or a catalyst precursor in various chemical reactions. Its metal-chelating properties facilitate the acceleration of reactions, making it a popular choice in catalysis.
Used in Organic Synthesis:
Phenol oxazoline is employed as a reagent or intermediate in organic synthesis. Its unique structure allows for the creation of a wide range of organic compounds.
Used in Medicinal Chemistry and Drug Development:
Phenol oxazoline is used as a chelating agent for metal-based pharmaceuticals. Its ability to form stable complexes with metal ions makes it a promising candidate for the development of new drugs and therapies.

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

Upstream product

• 767-00-0 4-cyanophenol 
• 141-43-5 ethanolamine 
• 99-76-3 methyl 4-hydroxylbenzoate 
• 25984-63-8 4-hydroxythiobenzamide 
• 99-96-7 4-hydroxy-benzoic acid 
• 75268-14-3 4-hydroxy-N-(2-hydroxyethyl)-benzamide 
• 81428-57-1 4-Hydroxybenzolcarboximidsaeure-2-bromethylester-hydrochlorid 
• 1517-05-1 2-azidoethanol 
• 123-08-0 4-hydroxy-benzaldehyde 

Downstream Products

• 13676-94-3 2-(4-methoxyphenyl)-4,5-dihydrooxazole 
• 99855-09-1 2-(4-ethoxyphenyl)-4,5-dihydro-1H-oxazole 
• 1451377-36-8 C₂₀H₁₇NO₅ 
• 1146362-08-4 tert.butyl 4-[4-(4,5-dihydroxazol-2-yl)-phenoxyl]-piperidine-1-carboxylate 
• 1165760-92-8 (4-methyl)-benzylcarbamic acid 4-(4,5-dihydrooxazol-2-yl)phenyl ester 
• 1165760-91-7 (2-methyl)-benzylcarbamic acid 4-(4,5-dihydrooxazol-2-yl)phenyl ester 

Relevant articles and documents

Ultrasound-Accelerated, Concise, and Highly Efficient Synthesis of 2-Oxazoline Derivatives Using Heterogenous Calcium Ferrite Nanoparticles and Their DFT Studies

A rapid and operationally simple approach for synthesising biologically relevant 2-oxazoline derivatives has been developed through highly efficient ultrasound-promoted coupling reactions of thioamides and amino alcohols using calcium ferrite nanoparticles as heterogeneous catalysts. The major advantage of using ultrasound irradiation lies in the drastic reduction of reaction time as compared with conventional stirring. Furthermore, quantum chemical investigations for the synthesised 2-oxazoline derivatives have been carried out at the DFT/B3LYP/6-311 + G (d, p) level of theory to predict the optimized geometry. The molecular properties such as bond lengths, bond orders, Milliken charges, frontier molecular orbitals, global reactivity descriptors, molecular electrostatic potential map, and thermodynamic parameters of all the compounds have also been reported at the same level of theory.

In Vitro Antiviral Activity of New Oxazoline Derivatives as Potent Poliovirus Inhibitors

The final stages of polio eradication are proving more difficult than the early phases, and the development of effective drugs and treatments is considered a priority; thus, the research is ongoing. A screening of our in-house chemical library against poliovirus Sabin strains led to the identification of compounds 5 and 6 as hits active at submicromolar concentrations. Derivatives of these compounds were synthesized as a preliminary structure-activity-relationship study. Among them, 7 and 11 were highly active against poliovirus Sabin 1-3. Compound 11 was also very potent against a large panel of wild and vaccine-derived polioviruses. Time-of-addition experiments suggest that 5 and 7 could be active at an early stage of viral replication, whereas 11 was active at same concentration at all stages of viral replication. A ligand-based approach was applied to find the common structural features shared by the new compounds and already-known poliovirus inhibitors.

OXAZOLINE COMPOUND, CROSSLINKER AND RESIN COMPOSITION

PROBLEM TO BE SOLVED: To provide an oxazoline compound and trioxazoline compound optimal as crosslinkers for a wide range of uses, including a coating agent, ink, a film, a binder, and adhesive or the like. SOLUTION: The present invention provides an oxazoline compound represented by the following chemical formula, a trioxazoline compound obtained by trifunctionalizing the oxazoline compound represented by the following chemical formula, and a crosslinker and a resin composition using the oxazoline compound or the trioxazoline compound. In the formula, X is H or R-OH, R is a C1-4 linear or branched alkylene group. SELECTED DRAWING: None COPYRIGHT: (C)2019,JPO&INPIT

OXAZOLINE COMPOUND, CROSSLINKING AGENT AND RESIN COMPOSITION

PROBLEM TO BE SOLVED: To provide an oxazoline compound optimal as a crosslinking agent in a wide range of applications such as a coating agent, ink, a film, a binder and an adhesive. SOLUTION: There are provided an oxazoline compound represented by the following chemical formula, and a crosslinking agent and a resin composition using the oxazoline compound. In the formula, X is a group having a carbon-carbon double bond, and is a group containing an acrylic group or a methacrylic group. SELECTED DRAWING: None COPYRIGHT: (C)2020,JPOandINPIT

A Fluorescence Polarization Assay for Binding to Macrophage Migration Inhibitory Factor and Crystal Structures for Complexes of Two Potent Inhibitors

Human macrophage migration inhibitory factor (MIF) is both a keto-enol tautomerase and a cytokine associated with numerous inflammatory diseases and cancer. Consistent with observed correlations between inhibition of the enzymatic and biological activities, discovery of MIF inhibitors has focused on monitoring the tautomerase activity using l-dopachrome methyl ester or 4-hydroxyphenyl pyruvic acid as substrates. The accuracy of these assays is compromised by several issues including substrate instability, spectral interference, and short linear periods for product formation. In this work, we report the syntheses of fluorescently labeled MIF inhibitors and their use in the first fluorescence polarization-based assay to measure the direct binding of inhibitors to the active site. The assay allows the accurate and efficient identification of competitive, noncompetitive, and covalent inhibitors of MIF in a manner that can be scaled for high-throughput screening. The results for 22 compounds show that the most potent MIF inhibitors bind with Kd values of ca. 50 nM; two are from our laboratory, and the other is a compound from the patent literature. X-ray crystal structures for two of the most potent compounds bound to MIF are also reported here. Striking combinations of protein-ligand hydrogen bonding, aryl-aryl, and cation-π interactions are responsible for the high affinities. A new chemical series was then designed using this knowledge to yield two more strong MIF inhibitors/binders.

Willgerodt–Kindler reaction-driven one pot solventless entry to 2-oxazolines

We report an efficient and green protocol for the synthesis of 2-oxazolines by the reaction of aromatic nitriles with β-aminoalcohols using sulfur under solvent-free conditions. The reaction occurs via the Willgerodt-Kindler mechanism followed by transami

Ruthenium(II) 8-quinolinolates: Synthesis, characterization, crystal structure and catalysis in the synthesis of 2-oxazolines

Abstract New octahedral ruthenium(II) complexes (1-4) have been synthesized from the reaction of ruthenium(II) precursors [RuHCl(CO)(EPh3)3] (E = P or As) with the bidentate Schiff base ligands, 2-((2,6-dimethylphenylimino)methyl)quinolin-8-ol (L1) and 2-((2,6-diisopropylphenylimino)methyl)quinolin-8-ol (L2) in ethanol. These complexes have been characterized by elemental analyses, IR, UV-Vis, 1H, 13C and 31P NMR and ESI-Mass spectroscopy. The molecular structure of the complex [RuCl(CO)(PPh3)2(L2)] (2) was determined by single-crystal X-ray diffraction, which reveals a distorted octahedral geometry around ruthenium(II) ion. The catalytic activity of the new complexes was evaluated for the condensation of nitriles with ethanolamine under solvent free conditions. The processes were operative with aromatic and heteroaromatic nitriles and tolerated several substitutional groups. The studies on the effect of substitution over ligands, coligands, reaction time, temperature and catalyst loading were carried out in order to find the best catalyst in this series of complexes and favorable reaction conditions. A probable mechanism for the catalytic condensation of nitrile has also been proposed. The catalyst was recovered and recycled up to five times without significant loss of its activity.

A mild and efficient synthesis of 2-oxazolines via transamidation- cyclodehydrosulfurisation of thioamides with 2-aminoethanol

Transamidation of thioamides with 2-aminoethanol, followed by cyclodehydrosulfurisation of the resultant N-(β-hydroxyethyl)thioamides, has been utilised for the mild and efficient synthesis of 2-oxazolines. The developed protocol was found to be of general applicability. Georg Thieme Verlag KG Stuttgart · New York.

An efficient, eco-friendly, one-pot protocol for the synthesis of 2-oxazolines promoted by ionic liquid/indium chloride

2-Oxazolines have been synthesized using a solventless ionic liquid melt in good yields at ambient temperatures. The efficiency of various Lewis acid catalysts for the same reaction has been compared. The effectiveness of different alkyl chains in the ionic liquids for the synthesis of oxazolines has been studied and a butylmethylimidazolinium chloride/indium chloride melt has been found to be the best media for promoting the reaction. CSIRO 2006.

Three isomeric forms of hydroxyphenyl-2-oxazoline: 2-(2-hydroxyphenyl)-2- oxazoline, 2-(3-hydroxyphenyl)-2-oxazoline and 2-(4-hydroxyphenyl)-2-oxazoline

Crystal structures are reported for three isomeric compounds, namely 2-(2-hydroxyphenyl)-2-oxazoline, (I), 2-(3-hydroxyphenyl)-2-oxazoline, (II), and 2-(4-hydroxyphenyl)-2-oxazoline, (III), all C9H9NO 2 [systematic names: 2-(4,5-dihydro-1,3-oxazol-2-yl)phenol, (I), 3-(4,5-dihydro-1,3-oxazol-2-yl)phenol, (II), and 4-(4,5-dihydro-1,3-oxazol-2-yl) phenol, (III)]. In these compounds, the deviation from coplanarity of the oxazoline and benzene rings is dependent on the position of the hydroxy group on the benzene ring. The coplanar arrangement in (I) is stabilized by a strong intramolecular O-H...N hydrogen bond. Surprisingly, the 2-oxazoline ring in molecule B of (II) adopts a 3T4 (C2T C3) conformation, while the 2-oxazoline ring in molecule A, as well as that in (I) and (III), is nearly planar, as expected. Tetramers of molecules of (II) are formed and they are bound together via weak C-H...N hydrogen bonds. In (III), strong intermolecular O-H...N hydrogen bonds and weak intramolecular C-H...O hydrogen bonds lead to the formation of an infinite chain of molecules perpendicular to the b direction. This paper also reports a theoretical investigation of hydrogen bonds, based on density functional theory (DFT) employing periodic boundary conditions.