Production Method 1

151230-42-1

944898-79-7

Reaction Conditions

1.1 Reagents: Selenium dioxide Solvents: 1,4-Dioxane ;  6 h, 100 °C

Reference

Aza-heteroaryl compounds as PI3K-gamma inhibitors and their preparation

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6-Bromo-benzooxazole-2-carbaldehyde Raw materials

• 6-bromo-2-methyl-1,3-benzoxazole

6-Bromo-benzooxazole-2-carbaldehyde Preparation Products

• 6-Bromo-benzooxazole-2-carbaldehyde (944898-79-7)

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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Benzoxazoles Benzoxazoles
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Benzoxazoles

6-Bromo-benzooxazole-2-carbaldehyde: A Comprehensive Overview

The compound 6-Bromo-benzooxazole-2-carbaldehyde (CAS No. 944898-79-7) is a highly specialized organic molecule that has garnered significant attention in the fields of organic chemistry, pharmacology, and materials science. This compound belongs to the class of benzooxazoles, which are known for their unique structural properties and diverse applications. The presence of a bromine atom at the 6-position and an aldehyde group at the 2-position imparts distinct chemical reactivity and biological activity to this molecule. Recent studies have highlighted its potential in drug discovery, particularly in the development of anticancer agents and antimicrobial compounds.

Benzooxazoles are heterocyclic aromatic compounds characterized by a six-membered ring containing two nitrogen atoms. The substitution pattern in 6-Bromo-benzooxazole-2-carbaldehyde plays a crucial role in determining its electronic properties and reactivity. The aldehyde group at the 2-position introduces electrophilic character, making it susceptible to nucleophilic attacks. Meanwhile, the bromine atom at the 6-position contributes to the molecule's stability and enhances its ability to participate in various chemical transformations. This combination makes 6-Bromo-benzooxazole-2-carbaldehyde a versatile building block in organic synthesis.

Recent advancements in synthetic methodologies have enabled the efficient preparation of 6-Bromo-benzooxazole-2-carbaldehyde. One notable approach involves the oxidation of a suitable benzoxazole derivative using oxidizing agents such as KMnO4 or CrO3 under controlled conditions. This method ensures high yield and purity, making it suitable for large-scale production. Additionally, researchers have explored alternative routes involving microwave-assisted synthesis and catalytic systems to optimize reaction conditions further.

The applications of 6-Bromo-benzooxazole-2-carbaldehyde are not limited to organic synthesis. Its unique electronic properties make it an attractive candidate for use in pharmaceuticals, agrochemicals, and advanced materials. For instance, studies have demonstrated its potential as a precursor for constructing bioactive molecules with anticancer properties. In one recent investigation, derivatives of 6-Bromo-benzooxazole-2-carbaldehyde exhibited significant cytotoxicity against various cancer cell lines, suggesting their potential as lead compounds for drug development.

In addition to its pharmacological applications, 6-Bromo-benzooxazole-2-carbaldehyde has shown promise in materials science. Its ability to form stable coordination complexes with metal ions has led to its exploration as a ligand in catalysis and sensing applications. For example, researchers have reported the use of this compound as a sensing platform for detecting metal ions such as Fe3+ and Al3+ in aqueous solutions. The high sensitivity and selectivity of these sensors make them valuable tools in environmental monitoring and clinical diagnostics.

The toxicity profile of 6-Bromo-benzooxazole-2-carbaldehyde is another critical aspect that has been extensively studied. While it exhibits potent biological activity, its toxicity towards non-target cells must be carefully evaluated to ensure safe use in therapeutic applications. Recent studies have employed computational toxicology models to predict the compound's potential risks, providing valuable insights into its safety profile.

In conclusion, 6-Bromo-benzooxazole-2-carbaldehyde (CAS No. 944898-79-7) is a multifaceted compound with immense potential across various scientific domains. Its unique structure, versatile reactivity, and diverse applications make it a subject of intense research interest. As advancements in synthetic chemistry continue to unfold, the utility of this compound is expected to expand further, paving the way for innovative solutions in medicine, materials science, and beyond.

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