80281-50-1

Basic information

• Product Name: Oxazole, 5-(bromomethyl)-2-phenyl-
• Synonyms: 5-Bromomethyl-2-phenyl-oxazole;5-bromomethyl-2-phenyloxazole
• CAS NO: 80281-50-1
• Molecular Formula: C10H8BrNO
• Molecular Weight: 238.084
• Mol File: 80281-50-1.mol
• Article Data: 9

Chemical Properties

• Melting Point: 68 - 70 °C
• CAS DataBase Reference: Oxazole, 5-(bromomethyl)-2-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Oxazole, 5-(bromomethyl)-2-phenyl-(80281-50-1)
• EPA Substance Registry System: Oxazole, 5-(bromomethyl)-2-phenyl-(80281-50-1)

Safety Data

• Hazardous Substances Data: 80281-50-1(Hazardous Substances Data)

Upstream product

• 146896-52-8 2-phenyl-5-methylene-4,5-dihydrooxazole 
• 98-88-4 benzoyl chloride 
• 55-21-0 benzamide 
• 10283-95-1 N-allylbenzamide 
• 50487-77-9 N-(2,3-dibromopropyl)benzamide 
• 90701-93-2 (E)-5-bromomethylene-2-phenyl-4,5-dihydro-oxazole 

Downstream Products

• 838892-99-2 2-(2-phenyloxazol-5-ylmethyl)isoindole-1,3-dione 
• 719308-17-5 3,6-diethoxy-(2R)-2-isopropyl-(5S)-5-(2-phenyl-oxazol-5-ylmethyl)-2,5-dihydro-pyrazine 
• 1201042-16-1 (R)-1-(2-phenyl-oxazol-5-ylmethyl)-3-((S)-2-phenyl-2-piperidin-1-yl-propionyloxy)-1-azonia-bicyclo[2.2.2]octane bromide 
• 80281-51-2 5-((methylthio)methyl)-2-phenyloxazole 

Relevant articles and documents

Chromium-Catalyzed Asymmetric Dearomatization-Addition Reactions of Halomethyloxazoles and Indoles

The asymmetric dearomatization-addition reaction of halomethyloxazoles and halomethylindoles with aldehydes is realized in the presence of a carbazole-based bisoxazoline CrCl 2 complex to afford the corresponding enantioenriched, hydroxylated oxazoline and indoline products. The observed excellent chemo-, regio-, diastereo- and enantioselectivities are notable advantages of this protocol. The strategy established in this study is expected to find application in the synthesis of azaheterocycles with biological significance and useful functionalities.

Lead Optimization Generates CYP11B1 Inhibitors of Pyridylmethyl Isoxazole Type with Improved Pharmacological Profile for the Treatment of Cushing's Disease

Cushing's disease, characterized by elevated plasma cortisol levels, can be controlled by inhibition of 11β-hydroxylase (CYP11B1). The previously identified selective and potent CYP11B1 inhibitor 5-((5-methylpyridin-3-yl)methyl)-2-phenylpyridine Ref 7 (IC50= 2 nM) exhibited promutagenic potential as well as very low oral bioavailability in rats (F = 2%) and was therefore modified to overcome these drawbacks. Successful lead optimization resulted in similarly potent and selective 5-((5-methoxypyridin-3-yl)methyl)-3-phenylisoxazole 25 (IC50 = 2 nM, 14-fold selectivity over CYP11B2), exhibiting a superior pharmacological profile with no mutagenic potential. Furthermore, compound 25 inhibited rat CYP11B1 (IC50 = 2 μM) and showed a high oral bioavailability (F = 50%) and sufficient plasma concentrations in rats, providing an excellent starting point for a proof-of-principle study.

Catalyst-free intramolecular oxidative cyclization of N-allylbenzamides: A new route to 2,5-substituted oxazoles

A catalyst-free intramolecular oxidative cyclization reaction of N-allylbenzamides has been developed to prepare 2,5-disubstituted oxazoles with good yields. This reaction gives an efficient synthetic strategy to form an oxazole nucleus directly from easi