53416-46-9

Basic information

• Product Name: 2-(4-METHOXYPHENYL)-4,4-DIMETHYL-4,5-DIHYDRO-1,3-OXAZOLE
• Synonyms: 4,4-dimethyl-2-(4-methoxyphenyl)-2-oxazoline;4,5-dihydro-4,4-dimethyl-2-(4-methoxyphenyl)-oxazol;2-(4-METHOXYPHENYL)-4,4-DIMETHYL-4,5-DIHYDRO-1,3-OXAZOLE;2-(4-Methoxyphenyl)-4,4-dimethyl-4,5-dihdro-1,3-oxazole;4,5-Dihydro-4,4-dimethyl-2-(4-methoxyphenyl)-1,3-oxazole;Oxazole,4,5-dihydro-2-(4-methoxyphenyl)-4,4-dimethyl-
• CAS NO: 53416-46-9
• Molecular Formula: C₁₂H₁₅NO₂
• Molecular Weight: 205.25
• Product Categories: Oxazoles, Isoxazoles & Benzoxazoles;Oxazoles, Isoxazoles & Benzoxazoles
• Mol File: 53416-46-9.mol

Chemical Properties

• Boiling Point: 302.9°C at 760 mmHg
• Flash Point: 112.6°C
• Appearance: /
• Density: 1.08g/cm³
• Vapor Pressure: 0.00173mmHg at 25°C
• Refractive Index: 1.531
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-(4-METHOXYPHENYL)-4,4-DIMETHYL-4,5-DIHYDRO-1,3-OXAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-METHOXYPHENYL)-4,4-DIMETHYL-4,5-DIHYDRO-1,3-OXAZOLE(53416-46-9)
• EPA Substance Registry System: 2-(4-METHOXYPHENYL)-4,4-DIMETHYL-4,5-DIHYDRO-1,3-OXAZOLE(53416-46-9)

Safety Data

• Hazardous Substances Data: 53416-46-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
DMO serves as a crucial intermediate in the synthesis of various pharmaceuticals and agrochemicals, contributing to the development of new drugs and pesticides. Its unique chemical structure allows for the creation of a wide range of compounds with different therapeutic and pesticidal properties.
Used in Antifungal and Antibacterial Applications:
DMO has been studied for its potential antifungal and antibacterial properties, making it a candidate for use in treatments and preventive measures against fungal and bacterial infections.
Used in Electronics Industry:
In the field of electronics, DMO has been utilized in the development of organic light-emitting diodes (OLEDs). Its ability to act as a fluorescence emitter in organic electroluminescent devices makes it a valuable component in creating advanced display technologies and lighting solutions.
Overall, 2-(4-Methoxyphenyl)-4,4-dimethyl-4,5-dihydro-1,3-oxazole is a multifaceted chemical compound with significant applications across various industries, including pharmaceuticals, agriculture, and electronics. Its versatility and potential for further research and development make it an important substance in the ongoing pursuit of innovative solutions in these fields.

InChI:InChI=1/C12H15NO2/c1-12(2)8-15-11(13-12)9-4-6-10(14-3)7-5-9/h4-7H,8H2,1-3H3

Upstream product

• 53244-68-1 2-(methylthio)-4,4-dimethyl-4,5-dihydro-1,3-oxazole 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 94615-60-8 N-(1,1-dimethyl-2-hydroxyethyl)-p-methoxybenzamide 
• 100-07-2 4-methoxy-benzoyl chloride 
• 124-68-5 2-Amino-2-methyl-1-propanol 
• 100-09-4 4-methoxybenzoic acid 
• 874-90-8 4-methoxybenzonitrile 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 129665-83-4 Li(4,4-dimethyl-2-oxazolinyl) 
• 4231-69-0 1-(4-methoxybenzoyl)-1H-1,2,3-benzotriazole 
• 30093-99-3 4,4-dimethyl-2-oxazoline 
• 696-62-8 para-iodoanisole 
• 623-12-1 4-chloromethoxybenzene 
• 123-11-5 4-methoxy-benzaldehyde 

Downstream Products

• 56446-27-6 2-(4,4-dimethyl-4,5-dihydro-oxazol-2-yl)-5-methoxy-N-methyl-thiobenzamide 
• 56446-25-4 2-(4,4-dimethyl-4,5-dihydro-oxazol-2-yl)-5-methoxy-benzaldehyde 
• 56446-26-5 2-(4-methoxy-2-phenylsulfanyl-phenyl)-4,4-dimethyl-4,5-dihydro-oxazole 
• 88932-58-5 2-(4-Methoxy-2-(trimethylsilyl)phenyl)-4,4-dimethyl-2-oxazoline 
• 130131-83-8 2-(2-Hydroxy-1,1-dimethyl-ethyl)-5-methoxy-isoindole-1,3-dione 
• 130131-79-2 Bis-[2-(4,4-dimethyl-4,5-dihydro-oxazol-2-yl)-5-methoxy-phenyl]-methanone 
• 25452-29-3 2-(((4-methoxyphenyl)methyl)amino)-2-methylpropanol 
• 874-90-8 4-methoxybenzonitrile 
• 86917-40-0 2-<2-hydroxy(phenyl)methyl-4-methoxyphenyl>-4,4-dimethyl-2-oxazoline 
• 102041-31-6 2-(2-Allyl-4-methoxyphenyl)-4,4-dimethyl-2-oxazoline 
• 94615-63-1 (5S,6S)-5-(4-Methoxy-phenyl)-2,2-dimethyl-6-phenoxy-4-oxa-1-aza-bicyclo[3.2.0]heptan-7-one 
• 75817-44-6 2-(2-methyl-4-methoxyphenyl)4,4-dimethyl-2-oxazoline 
• 133341-98-7 2-(4-Methoxy-2,6-dimethyl-phenyl)-4,4-dimethyl-4,5-dihydro-oxazole 
• 194360-11-7 5-(4,4-dimethyl-4,5-dihydrooxazole-2-yl)-2-methoxybenzaldehyde 

Relevant articles and documents

Preparation of Polyfunctionalized Aromatic Nitriles from Aryl Oxazolines

A selective ortho,ortho’-functionalization of readily available aryl oxazolines by two successive magnesiations with sBu2Mg in toluene followed by trapping reactions with electrophiles, such as (hetero)aryl iodides or bromides, iodine, tosyl cyanide, ethyl cyanoformate or allylic bromides (39 examples, 62–99 % yield) is reported. Treatment of these aryl oxazolines with excess oxalyl chloride and catalytic amounts of DMF (50 °C, 4 h) provided the corresponding nitriles (36 examples, 73–99 % yield). Conversions of these nitriles to valuable heterocycles are reported, and a tentative mechanism is proposed.

Substitution Effect on 2-(Oxazolinyl)-phenols and 1,2,5-Chalcogenadiazole -Annulated Derivatives: Emission-Color-Tunable, Minimalistic Excited-State Intramolecular Proton Transfer (ESIPT)-Based Luminophores

Minimalistic 2-(oxazolinyl)-phenols substituted with different electron-donating and -withdrawing groups as well as 1,2,5-chalcogenadiazole-annulated derivatives thereof were synthesized and investigated in regard to their emission behavior in solution as well as in the solid state. Depending on the nature of the incorporated substituent and its position, emission efficiencies were increased or diminished, resulting in AIE or ACQ characteristics. Single-crystal analysis revealed J- and H-type packing motifs and a so-far undescribed isolation of ESIPT-based fluorophores in the keto form.

Aerobic C(sp2)-H Hydroxylations of 2-Aryloxazolines: Fast Access to Excited-State Intramolecular Proton Transfer (ESIPT)-Based Luminophores

The direct hydroxylation of 2-aryloxazolines via a deprotonative magnesiation using TMPMgCl·LiCl and subsequent oxidation with molecular oxygen or air as a green oxidant is reported. This method proceeds under mild conditions at room temperature with high regioselectivity and chemoselectivity. The obtained phenols exhibit tunable luminescence properties, induced by excited-state intramolecular proton transfer. This method opens a new opportunity for the sustainable synthesis of luminescent organic molecules.

Palladium-catalyzed direct C2-arylation of azoles with aromatic triazenes

A highly efficient palladium-catalyzed arylation of azoles at the C2-position using 1-aryltriazenes as aryl reagents was developed. Azoles including oxazoles, thiazoles, imidazoles, 1,3,4-oxadiazoles, and oxazolines could react with 1-aryltriazenes smoothly to generate the corresponding products in good to excellent yields, and various substitution patterns were tolerated toward the reaction.

Synthesis of asymmetrically disubstituted anthracenes

We have developed synthetic pathways toward differently substituted hydroxyanthracenes (anthrols) with the aim to investigate their photochemical reactivity in dehydration reactions. Although the syntheses of anthracenes substituted at positions 9,10 are well known, reports for the synthesis of anthracenes with different substitution patterns are scarce. Herein we review known and report novel synthetic pathways toward anthrols with substituents at 1,2-, 2,3-, and 2,6- positions. We present two synthetic approaches: (i) building of the anthracene tricyclic fused ring system from the appropriate benzene derivatives, and (ii) reduction of the corresponding anthraquinones. Reduction of 2-hydroxyanthracene-1-carbaldehyde to the corresponding alcohol yields rather unexpected 1,1′-methylenedianthracen-2-ol, whose proposed mechanism of formation is supported by experimental observations and calculations.

Secondary Phosphine Oxide Preligands for Palladium-Catalyzed C–H (Hetero)Arylations: Efficient Access to Pybox Ligands

C–H arylations of oxazolines were accomplished with a well-defined palladium catalyst derived from a secondary bisdiamantyl phosphine oxide. The single-component secondary phosphine oxide (SPO)-palladium complex enabled C–H activations with aryl bromides

Palladium-catalyzed electrophilic C–H fluorination of arenes using oxazoline as a removable directing group

Dimethyloxazoline was rationally designed to act as a removable ortho-directing group (DG) for the palladium-catalyzed C–H electrophilic fluorination of arenes. Using NFSI as the fluorinating agent, and Pd(II), Ag(I) catalytic system, electrophilic C(sp2–H) ortho-fluorination took place on a variety of aryl substrates to afford the corresponding mono- and di-fluorinated products.

Photoinduced Copper-Catalyzed C-H Arylation at Room Temperature

Room-temperature azole C-H arylations were accomplished with inexpensive copper(I) compounds by means of photoinduced catalysis. The expedient copper catalysis set the stage for site-selective C-H arylations of non-aromatic oxazolines under mild reaction conditions, and provides step-economical access to the alkaloid natural products balsoxin and texamine. Copper light: Room-temperature C-H arylations of heteroarenes were accomplished with inexpensive copper compounds by photoinduced catalysis. The expedient copper catalysis leads to site-selective C-H arylations of non-aromatic oxazolines under mild reaction conditions, and provides step-economical access to the alkaloid natural products balsoxin and texamine.

Zincation of 4,4-dimethyloxazoline using TMPZnCl·LiCl. A new preparation of 2-aryloxazolines

The metalation of 4,4-dimethyloxazoline using TMPZnCl·LiCl provides a stable 2-zincated oxazolinyl reagent which readily undergoes palladium-catalyzed Negishi cross-couplings allowing a new access to 2-aryloxazolines. Cu-mediated acylation and allylation reactions also proceed in good yields. This journal is