143659-19-2

Basic information

• Product Name: 5-(4-METHYLPHENYL)-1,3-OXAZOLE
• Synonyms: 5-(4-METHYLPHENYL)-1,3-OXAZOLE;5-(4-METHYLPHENYL)OXAZOLE;4-(1,3-Oxazol-5-yl)toluene;5-(p-Tolyl)oxazole
• CAS NO: 143659-19-2
• Molecular Formula: C₁₀H₉NO
• Molecular Weight: 159.18
• Mol File: 143659-19-2.mol

Chemical Properties

• Melting Point: 65-67
• Boiling Point: 273.9 °C at 760 mmHg
• Flash Point: 108.6 °C
• Appearance: /
• Density: 1.082 g/cm³
• Vapor Pressure: 0.00936mmHg at 25°C
• Refractive Index: 1.539
• CAS DataBase Reference: 5-(4-METHYLPHENYL)-1,3-OXAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(4-METHYLPHENYL)-1,3-OXAZOLE(143659-19-2)
• EPA Substance Registry System: 5-(4-METHYLPHENYL)-1,3-OXAZOLE(143659-19-2)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 143659-19-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical and Agrochemical Synthesis:
5-(4-METHYLPHENYL)-1,3-OXAZOLE is utilized as a key building block in the creation of various pharmaceuticals and agrochemicals. Its unique chemical structure allows for the development of new compounds with potential therapeutic and pesticidal properties, contributing to advancements in drug discovery and agricultural chemistry.
Used in Materials Science:
In the field of materials science, 5-(4-METHYLPHENYL)-1,3-OXAZOLE may find applications due to its chemical properties, potentially enhancing the performance of certain materials or contributing to the development of novel materials with specific characteristics.
Used as a Reagent in Organic Chemistry Research:
5-(4-METHYLPHENYL)-1,3-OXAZOLE also serves as a valuable reagent in organic chemistry research, facilitating various chemical reactions and synthesis processes. Its presence can aid in the exploration of new reaction pathways and the synthesis of complex organic molecules.
Overall, 5-(4-METHYLPHENYL)-1,3-OXAZOLE is a versatile compound with applications spanning across different scientific disciplines, highlighting its importance in the realm of organic synthesis and beyond.

InChI:InChI=1/C10H9NO/c1-8-2-4-9(5-3-8)10-6-11-7-12-10/h2-7H,1H3

Upstream product

• 593-75-9 methyl isocyanate 
• 14062-78-3 N,N-dimethyl-4-toluamide 
• 68228-48-8 1-(p-toluoyl)-1,2,4-triazole 
• 38622-91-2 [(p-methylphenyl)sulfonylmethyl]isonitrile 
• 104-87-0 4-methyl-benzaldehyde 
• 288-42-6 oxazol 
• 106-38-7 para-bromotoluene 
• 104-81-4 4-Methylbenzyl bromide 
• 589-18-4 4-Methylbenzyl alcohol 
• 7163-50-0 (4-methylphenyl)(oxo)acetic acid 

Downstream Products

• 37009-57-7 2-phenyl-5-p-tolyloxazole 
• 1226890-13-6 5-(4-methylphenyl)-2-[(triisopropylsilyl)ethynyl]oxazole 
• 1402228-05-0 5-(4-methylphenyl)-2-{1-(pyrimidin-2-yl)-1H-indol-2-yl}oxazole 
• 1584688-10-7 C₁₇H₁₅NO 
• 1584688-14-1 C₁₅H₁₂N₂O 
• 1584688-13-0 C₁₅H₁₂N₂O 
• 1613376-85-4 5-(4-methylphenyl)-2-[naphthalen-2-yl(phenyl)methyl]oxazole 

Relevant articles and documents

Synthesis of Nanostructured Organosilicon Luminophores Based on Phenyloxazoles

A series of nanostructured organosilicon luminophores (NOLs) composed of a central 1,4-bis(5-phenyl-1,3-oxazol-2-yl)benzene (POPOP) acceptor chromophore and various peripheral p-terphenyl and 2,5-diphenyl-1,3-oxazole donor fragments have been synthesized for the first time using van Leusen reaction and direct palladium-catalyzed C-arylation of oxazole ring. Due to different functionalities of the silicon branching centers, NOLs with different donor-acceptor ratios have been obtained. The synthesized structures are expected to possess good optical characteristics for use in photonics and optoelectronics.

Tandem oxidative isocyanide-based cycloaddition reactions in the presence of MIL-101(Cr) as a reusable solid catalyst

The tandem oxidative three-component synthesis of two types of the heterocycles such as furans and imidazopyridines, via isocyanides [1+4] cycloaddition reactions in the presence of MIL-101(Cr) under aerobic conditions are reported. When the 4-toluenesulfonylmethyl isocyanide was used, an unexpected [3+2] cycloaddition reaction of isocyanides with aldehydes accomplished and dihydrophenyloxazoles and phenyloxazoles produced. These syntheses were successfully carried out using a wide scope of the substrates.

Targeted Polypharmacology: Discovery of a Highly Potent Non-Hydroxamate Dual Matrix Metalloproteinase (MMP)-10/-13 Inhibitor

Matrix metalloproteinases (MMPs) play a key role in many diseases like cancer, atherosclerosis or arthritis. Interest in MMP inhibition has been revitalized very recently as the knowledge on the underlying network of biological pathways is steadily growing. On the basis of this new insight into the relevance of MMP-10 and MMP-13 within the MMP network and the ban of hydroxamate inhibitors from clinical development, the discovery of non-hydroxamate multitarget drugs against specific MMPs is of foremost interest. Here, we disclose the discovery of a very potent and selective non-hydroxamate MMP-10/-13 inhibitor. The high potency (IC50 of 31 nM [MMP-10] and 5 nM [MMP-13]) and selectivity over MMP-1, -2, -3, -7, -8, -9, -12, and -14 enable this compound to decipher disease causing MMP networks and to generate new treatment options through targeted polypharmacology.

A One-Pot Tandem Approach for the Synthesis of 5-(Het)aryloxazoles from Substituted (Het)aryl Methyl Alcohols and Benzyl Bromides

A new modified van Leusen strategy has been developed for the synthesis of biologically significant 5-substituted oxazoles by the reaction of (het)aryl methyl alcohols or benzyl bromides as precursors with tosylmethylisocyanide (TosMIC) under basic conditions. This method is efficient, takes place under mild reaction conditions, and is tolerant of various functional groups with high yield.

Tandem cycloaddition-decarboxylation of α-keto acid and isocyanide under oxidant-free conditions towards monosubstituted oxazoles

An efficient method, tandem [3 + 2] cycloaddition-decarboxylation of α-keto acid and isocyanide promoted by copper salt, has been developed. Under oxidant-free conditions, a series monosubstituted oxazoles have been constructed. Different from the traditional application of α-oxo acids as acyl surrogates, the elegant approach herein ingeniously avoids consuming excess oxidants.

A robust and efficient catalyst possessing an electron-deficient ligand for the palladium-catalyzed direct arylation of heteroarenes

The exploration of the direct arylation capacity of a unique, thermally stable, and air-stable Pd0-phosphine catalyst is reported. Besides decisively contributing to catalyst robustness, the electron-deficient trifluoromethyl-substituted triphenylphosphine ligands make the palladium center more electron-deficient and accelerate the direct arylation step. The combination of only 0.5-2 mol-% of the catalyst and a substoichiometric quantity of pivalic acid generates an efficient system to promote biaryl-forming reactions of a broad range of electronically varied hetarenes and aryl bromides. The observed regioselective arylations suggest that a concerted metalation-deprotonation pathway is involved in the C-H activation step.

Synthesis and biological activity of 5-(4-methoxyphenyl)-oxazole derivatives

5-(4′-Methoxyphenyl)-oxazole (MPO), originally reported as a synthetic compound, was isolated from fungal culture broth as an inhibitor of hatch and growth of Caenorhabditis elegans. Nineteen MPO derivatives were chemically synthesized, but showed no effect on C. elegans hatch and growth. These findings strongly suggested that the whole structure of MPO is essential for anti-C. elegans activity.

Mild palladium-catalyzed regioselective direct arylation of azoles promoted by tetrabutylammonium acetate

A mild, general, and convenient palladium-catalyzed direct arylation of the 5-position of azoles with aryl bromides, efficiently promoted by tetrabutylammonium acetate, is described. 1-Methylpyrazole, oxazole, and thiazole reacted at 70°C in N,N-dimethyla

Copper-mediated C-H/C-H biaryl coupling of benzoic acid derivatives and 1,3-azoles

Hot couple: A precious-metal-free copper-mediated intermolecular direct biaryl coupling of benzoic acid derivatives and 1,3-azoles has been developed. The key to success is the installation of an amide-based bidentate coordinating group, which is easily removed and transformed into the parent ester groups after the coupling reaction. Kinetic studies indicate that the rate-limiting step is the aromatic C-H bond cleavage of benzoic acid derivatives. Copyright

Copper-mediated dehydrogenative biaryl coupling of naphthylamines and 1,3-azoles

A copper-mediated dehydrogenative biaryl cross-coupling of naphthylamines and 1,3-azoles has been developed. The key to its success is the introduction of N,N-bidentate coordination system based on the picolinamide directing group. The reaction proceeds s