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Benzoyl Chloride, 4-Iodo-3-Methyl-

Benzoyl chloride, 4-iodo-3-methyl- (CAS No. 52107-94-5) is a highly reactive aromatic compound with significant applications in organic synthesis and materials science. This compound is characterized by its unique structure, which includes a benzoyl group substituted with an iodine atom at the para position and a methyl group at the meta position relative to the carbonyl group.

The molecular formula of benzoyl chloride, 4-iodo-3-methyl- is C8H7ClI, and its molecular weight is approximately 236 g/mol. The compound exists as a crystalline solid under standard conditions, with a melting point of around 80°C and a boiling point of approximately 180°C under normal pressure. Its density is about 1.5 g/cm3, making it relatively dense compared to many organic compounds.

One of the most notable features of benzoyl chloride, 4-iodo-3-methyl- is its reactivity due to the presence of the acyl chloride group (-COCl). This functional group makes the compound highly electrophilic, enabling it to undergo various nucleophilic acyl substitution reactions with alcohols, phenols, and amines to form corresponding esters or amides. The iodine substituent at the para position further enhances the reactivity of the molecule by introducing electron-withdrawing effects, which stabilize intermediates during reactions.

Recent studies have highlighted the potential of benzoyl chloride, 4-iodo-3-methyl- in the synthesis of advanced materials such as polymeric membranes and optoelectronic devices. Researchers have demonstrated that this compound can serve as a precursor for generating highly ordered self-assembled monolayers (SAMs) on various substrates, which are crucial for applications in sensors and nanotechnology.

In addition to its role in material science, benzoyl chloride, 4-iodo-3-methyl- has shown promise in medicinal chemistry as an intermediate in the synthesis of bioactive compounds. For instance, it has been used to prepare derivatives with potential anti-inflammatory and anticancer properties through strategic substitution reactions.

The synthesis of benzoyl chloride, 4-iodo-3-methyl- typically involves Friedel-Crafts acylation followed by iodination or direct substitution reactions using appropriate alkyl halides. These methods ensure high yields and purity levels suitable for both academic research and industrial applications.

From an environmental standpoint, understanding the degradation pathways of benzoyl chloride, 4-iodo-3-methyl- is critical for assessing its ecological impact. Recent research indicates that this compound undergoes hydrolysis in aqueous environments to form corresponding carboxylic acids and hydrogen chloride gas under certain conditions.

In conclusion, benzoyl chloride, 4-iodo-3-methyl-, CAS No. 52107945, remains a versatile building block in organic synthesis with expanding applications across multiple disciplines due to its unique chemical properties and reactivity profiles.

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