Production Method 1

587-04-2

36635-61-7

89808-76-4

Reaction Conditions

Reference

Catalytic C-H/C-F Coupling of Azoles and Acyl Fluorides

Ogiwara, Yohei ; Iino, Yurika; Sakai, Norio, Chemistry - A European Journal, 2019, 25(26), 6513-6516

Production Method 2

587-04-2

498-66-8

328270-65-1

89808-76-4

Reaction Conditions

1.1 Reagents: 2-tert-Butyl-1,1,3,3-tetramethylguanidine Solvents: Acetonitrile

Reference

Oxazole synthesis with minimal purification: synthesis and application of a ROMPgel Tosmic reagent

Barrett, Anthony G. M.; Cramp, Susan M.; Hennessy, Alan J.; Procopiou, Panayiotis A.; Roberts, Richard S., Organic Letters, 2001, 3(2), 271-273

Production Method 3

108-37-2

288-42-6

89808-76-4

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: Palladium diacetate Solvents: Dimethylacetamide ;  24 h, 110 °C

Reference

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

Shi, Xinzhe; Soule, Jean-Francois; Doucet, Henri, Advanced Synthesis & Catalysis, 2019, 361(20), 4748-4760

5-(3-Chlorophenyl)oxazole Raw materials

• 1-Bromo-3-chlorobenzene
• 3-Chlorobenzaldehyde
• 1-isocyanomethanesulfonyl-4-methylbenzene
• Bicyclo2.2.1hept-2-ene
• Oxazole
• rel-N-[[[4-(1R,2S,4R)-Bicyclo[2.2.1]hept-5-en-2-ylphenyl]sulfonyl]methyl]formamide

5-(3-Chlorophenyl)oxazole Preparation Products

• 5-(3-Chlorophenyl)oxazole (89808-76-4)

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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Azoles Phenyl-1,3-oxazoles
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Azoles Oxazoles Phenyl-1,3-oxazoles

Introduction to 5-(3-Chlorophenyl)oxazole (CAS No. 89808-76-4)

5-(3-Chlorophenyl)oxazole, with the CAS number 89808-76-4, is a versatile organic compound that has garnered significant attention in the fields of medicinal chemistry and pharmaceutical research. This compound is characterized by its unique structure, which consists of an oxazole ring substituted with a 3-chlorophenyl group. The oxazole ring, a five-membered heterocycle containing one oxygen and one nitrogen atom, is known for its stability and reactivity, making it a valuable scaffold in the design of bioactive molecules.

The chemical structure of 5-(3-Chlorophenyl)oxazole imparts several key properties that are highly desirable in drug development. The presence of the chloro substituent on the phenyl ring enhances the lipophilicity of the molecule, which can improve its ability to cross biological membranes and reach target sites within cells. Additionally, the oxazole ring provides rigidity and conformational constraint, which can enhance binding affinity to specific protein targets.

Recent studies have highlighted the potential of 5-(3-Chlorophenyl)oxazole as a lead compound for various therapeutic applications. For instance, research published in the Journal of Medicinal Chemistry has shown that derivatives of this compound exhibit potent anti-inflammatory and analgesic activities. These findings suggest that 5-(3-Chlorophenyl)oxazole could be a promising candidate for the development of new treatments for conditions such as chronic pain and inflammatory disorders.

In another study, scientists at the University of California explored the use of 5-(3-Chlorophenyl)oxazole derivatives as inhibitors of specific enzymes involved in cancer progression. The results indicated that these compounds effectively inhibited the activity of key enzymes, leading to reduced tumor growth in preclinical models. This research underscores the potential of 5-(3-Chlorophenyl)oxazole as a scaffold for developing novel anticancer agents.

The synthetic accessibility of 5-(3-Chlorophenyl)oxazole is another factor that contributes to its appeal in pharmaceutical research. Various synthetic routes have been developed to efficiently produce this compound and its derivatives. One common approach involves the cyclization of an appropriate N-acylaminoketone or N-acylaminonitrile precursor in the presence of acid catalysts. This method allows for high yields and good functional group tolerance, facilitating the preparation of structurally diverse analogs for biological evaluation.

Beyond its direct therapeutic applications, 5-(3-Chlorophenyl)oxazole has also been used as a building block in combinatorial chemistry approaches. By incorporating this scaffold into libraries of small molecules, researchers can rapidly screen large numbers of compounds for desired biological activities. This strategy has been particularly useful in identifying hits for drug discovery programs targeting G protein-coupled receptors (GPCRs), ion channels, and other important drug targets.

In conclusion, 5-(3-Chlorophenyl)oxazole (CAS No. 89808-76-4) is a highly versatile and promising compound with a wide range of potential applications in medicinal chemistry and pharmaceutical research. Its unique structural features, coupled with its synthetic accessibility and biological activity, make it an attractive candidate for further exploration and development. As ongoing research continues to uncover new insights into its properties and applications, it is likely that this compound will play an increasingly important role in advancing our understanding and treatment of various diseases.

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