54867-72-0

Basic information

• Product Name: 2,5-bis(4-chlorophenyl)oxazole
• Synonyms: 2,5-bis(4-chlorophenyl)oxazole
• CAS NO: 54867-72-0
• Molecular Weight: 290.149
• Mol File: 54867-72-0.mol

Chemical Properties

• CAS DataBase Reference: 2,5-bis(4-chlorophenyl)oxazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-bis(4-chlorophenyl)oxazole(54867-72-0)
• EPA Substance Registry System: 2,5-bis(4-chlorophenyl)oxazole(54867-72-0)

Safety Data

• Hazardous Substances Data: 54867-72-0(Hazardous Substances Data)

Upstream product

• 130340-68-0 N-(p-chlorobenzoyl)-2-(p-chlorophenyl)ethylamine 
• 288-42-6 oxazol 
• 106-39-8 bromochlorobenzene 

Relevant articles and documents

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.).

N -Bromosuccinimide as a Brominating Agent for the Transformation of N -H (or N -Benzyl) Ketoaziridines into Oxazoles

A novel procedure for the direct synthesis of 2,5-diaryloxazoles starting from N-H ketoaziridines is described. The method proceeds via the in situ formation of N-bromoketoaziridines in the presence of N-bromosuccinimide followed by the generation of intermediate azomethine ylides. A plausible mechanism for this transformation is proposed.

Iodine catalysed intramolecular C(sp3)-H functionalization: synthesis of 2,5-disubstituted oxazoles from N-arylethylamides

Iodine catalyzed synthesis of 2,5-disubstituted oxazoles from N-arylethylamides through intramolecular C(sp3)-H functionalization under metal-free conditions is described. The method is tolerable to a wide range of substrates having a variety of functional groups with moderate to good yields of the products.

C-C bond cleavage of keto-aziridines; synthesis of oxazoles via regio-controlled ring expansion

The ring expansion of keto-aziridines to the corresponding 2,5-diaryloxazoles in the presence of iodine in refluxing dimethyl sulfoxide, is described. A plausible mechanism for the synthesis of 2,5-diaryloxazoles is proposed.