156780-52-8

Basic information

• Product Name: 2-(4-Methoxy-phenyl)-oxazole
• Synonyms: 2-(4-Methoxy-phenyl)-oxazole
• CAS NO: 156780-52-8
• Molecular Formula: C₁₀H₉NO₂
• Molecular Weight: 175.18396
• Mol File: 156780-52-8.mol
• Article Data: 17

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-(4-Methoxy-phenyl)-oxazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-Methoxy-phenyl)-oxazole(156780-52-8)
• EPA Substance Registry System: 2-(4-Methoxy-phenyl)-oxazole(156780-52-8)

Safety Data

• Hazardous Substances Data: 156780-52-8(Hazardous Substances Data)

Usage

Structure

Five-membered aromatic ring with one oxygen and one nitrogen atom

Type

Oxazole derivative

Usage

Building block in the synthesis of pharmaceuticals and agrochemicals, reagent and intermediate for organic synthesis

Electron density

Increased by the presence of a methoxy group on the phenyl ring, which can result in altered chemical reactivity and potential medicinal properties

Biological activities

Studied for antimicrobial, antitumor, and anti-inflammatory properties, making it of interest for further exploration in drug development and discovery.

Upstream product

• 104-92-7 1-bromo-4-methoxy-benzene 
• 107-20-0 2-chloroethanal 
• 3424-93-9 4-methoxyphenylacetamide 
• 696-62-8 para-iodoanisole 
• 609345-33-7 oxazol-2-ylzinc(II) chloride 
• 288-42-6 oxazol 
• 213596-33-9 2-(4-methoxyphenyl)-5,5-dimethyl-1,3,2-dioxaborolane 
• 2032-35-1 Bromoacetaldehyde diethyl acetal 
• 1064706-48-4 2-(4-methoxyphenyl)-4,5-dihydro-5-diethylsulfonamideoxazole 
• 133950-90-0 N-(2,2-dimethoxy-ethyl)-4-methoxy-benzamide 

Downstream Products

• 87150-13-8 4-(oxazol-5-yl)benzonitrile 
• 68535-56-8 p-(2-oxazolyl)-phenol 
• 1020264-24-7 2-(4-methoxyphenyl)-5-(4-trifluoromethylphenyl)oxazole 
• 54867-73-1 2-(4-methoxyphenyl)-5-(4-methoxyphenyl)oxazole 
• 1020264-29-2 2-(4-methoxyphenyl)-5-naphthalen-1-yloxazole 
• 853656-44-7 5-(4-bromophenyl)-2-(4-methoxyphenyl)oxazole 
• 96907-66-3 2-(4-methoxyphenyl)-5-(4-methylphenyl)oxazole 
• 1020264-28-1 1-{4-[2-(4-methoxyphenyl)oxazol-5-yl]phenyl}ethanone 
• 118425-86-8 C₁₆H₁₂ClNO₂ 
• 1020264-22-5 2-(4-methoxyphenyl)-5-o-tolyloxazole 
• 1020264-26-9 2-(4-methoxyphenyl)-5-(3-nitrophenyl)oxazole 
• 17064-22-1 2-(4-methoxyphenyl)-5-phenyl oxazole 

Relevant articles and documents

Palladium- and copper-mediated direct C-2 arylation of azoles - Including free (NH)-imidazole, -benzimidazole and -indole - Under base-free and ligandless conditions

The first palladium- and copper-mediated C-2 arylations of thiazole, oxazole, N-methylimidazole and N-arylimidazoles, as well as of free (NH)-imidazole, -benzimidazole and -indole, with aryl iodides under ligandless and base-free conditions are described. Complete selectivity has been achieved under these unprecedented conditions, which allow the use of substrates containing base-sensitive groups, such the NH groups of imidazole, benzimidazole or indole, without their prior protection. No N-arylation products were detected in the arylation of free (NH)-imidazole, -benzimidazole and -indole. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

Efficient and highly regioselective direct C-2 arylation of azoles, including free (NH)-imidazole, -benzimidazole and -indole, with aryl halides

The Pd- and Cu-mediated reaction of a large variety of π-electron sufficient heteroarenes, which include free (NH)-imidazoles, -benzimidazole and -indole, with aryl iodides under ligandless and base-free conditions provides regioselectively the required 2-arylheterocycle derivatives in high yields. 2-Aryl-1-phenyl-1H-imidazoles can also be prepared by a one-pot domino HALEX and Pd- and Cu-mediated arylation reactions of 1-phenyl-1H-imidazole with activated and unactivated aryl bromides under base-free and ligandless conditions. The protocol for the synthesis of 2-arylazoles involving the use of aryl iodides has been found to be suitable for the efficient preparation of three bioactive compounds and a key intermediate in the synthesis of a heparanase inhibitor.

PdII-Catalyzed Regio- and Enantioselective Oxidative C?H/C?H Cross-Coupling Reaction between Ferrocenes and Azoles

Asymmetric C?H bond functionalization reaction is one of the most efficient and straightforward methods for the synthesis of optically active molecules. Herein we disclose an asymmetric C?H/C?H cross-coupling reaction of ferrocenes with azoles such as oxazoles and thiazoles. Palladium(II)/monoprotected amino acid (MPAA) catalytic system which exhibits excellent reactivity and regioselectivity for oxazoles and thiazoles. This method offers a powerful strategy for constructing planar chiral ferrocenes. Mechanistic studies suggest that the C?H bond cleavage of azoles is likely proceeding through a SEAr process and may not be a turnover limiting step.

Reaction Conditions for the Regiodivergent Direct Arylations at C2- or C5-Positions of Oxazoles using Phosphine-Free Palladium Catalysts

Two sets of reaction conditions for the regiodivergent C2- or C5- direct arylations of oxazole are reported. In both cases, phosphine-free catalysts and inexpensive bases were employed allowing the access to the arylated oxazoles in moderate to high yields. Using Pd(OAc)2/KOAc as catalyst and base, regioselective C5-arylations were observed; whereas, using Pd(acac)2/Cs2CO3 system, the arylation occurred at the C2-position of oxazole. The higher reactivity of C5-H bond of oxazole as compared to the C2-H bond in the presence of Pd(OAc)2/KOAc system is consistent with a concerted metalation deprotonation mechanism; whereas the C2-arylation likely occurs via a simple base deprotonation of the oxazole C2-position. Then, from these C2- or C5-arylated oxazoles, a second palladium-catalyzed direct C?H bond arylation affords 2,5-diaryloxazoles with two different aryl groups. We also applied these sequential arylations to the straightforward synthesis of 2-arylphenanthro[9,10-d]oxazoles via three C?H bond functionalization steps. The Ru-catalyzed C?H arylation of the aryl unit of 2-aryloxazoles is also described. (Figure presented.).