3-Methoxybenzamide
[CAS# 5813-86-5]

Identification

• Classification: Organic raw materials >> Amino compound >> Amide compound
• Name: 3-Methoxybenzamide
• Synonyms: m-Methoxybenzamide; m-Anisamide
• Molecular Formula: C₈H₉NO₂
• Molecular Weight: 151.16
• CAS Registry Number: 5813-86-5
• EC Number: 227-379-7
• SMILES: C1=C(C=CC=C1OC)C(N)=O

Properties

• Solubility: 1.409e+004 mg/L (25 ºC water)
• Density: 1.1±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.546, Calc.^*
• Melting point: 132.5-135.5 ºC (Expl.)
• Boiling Point: 319.72 ºC, 280.0±23.0 ºC (760 mmHg), Calc.^*
• Flash Point: 146.8±18.9 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Discovory and Applicatios

3-Methoxybenzamide is an aromatic organic compound derived from the benzoic acid structure, where a methoxy group (-OCH3) is attached to the third position of the benzene ring, and the carboxylic acid group is replaced by an amide group (-CONH2). Its molecular formula is C8H9NO2. This compound is of significant interest due to its versatile chemical reactivity and its utility as an intermediate in various organic synthesis processes. The discovery of 3-methoxybenzamide can be attributed to the exploration of methoxy-substituted aromatic compounds, which are widely studied for their potential biological and chemical properties.

The synthesis of 3-methoxybenzamide is typically achieved by reacting 3-methoxybenzoic acid with an amine or ammonia under appropriate conditions. One of the common methods involves acylation reactions, where a reagent such as thionyl chloride or acyl chlorides is used to convert the carboxylic acid group into an acyl chloride, which is then reacted with ammonia or an amine to form the amide bond. This approach provides a straightforward and efficient route for synthesizing 3-methoxybenzamide and other similar compounds. The presence of the methoxy group in the molecule enhances its solubility and reactivity, making it a versatile intermediate in various chemical reactions.

3-Methoxybenzamide finds several important applications in the pharmaceutical industry. It is often used as a building block for the synthesis of bioactive molecules, especially in drug discovery. The methoxy group and the amide functionality make the compound a useful template for developing more complex molecules that exhibit pharmacological activity. For example, 3-methoxybenzamide derivatives have been investigated for their potential antimicrobial, anticancer, and anti-inflammatory activities. The functional groups in the molecule provide sites for further modification, allowing for the design of compounds with improved selectivity and potency for specific biological targets.

In addition to its use in pharmaceuticals, 3-methoxybenzamide is also employed in the production of specialty chemicals. It serves as a precursor in the synthesis of dyes, pigments, and other organic materials. The methoxy group, being electron-donating, influences the electronic properties of the benzene ring, which can affect the color and stability of the resulting compounds. This makes 3-methoxybenzamide a valuable intermediate in the synthesis of organic dyes used in the textile, coating, and printing industries. The compound's ability to participate in electrophilic aromatic substitution reactions also facilitates the creation of a wide range of functionalized aromatic compounds.

Furthermore, 3-methoxybenzamide has applications in agrochemicals, particularly in the development of herbicides and pesticides. The amide functionality provides the compound with favorable binding characteristics to target enzymes and receptors in pests or weeds. Research has demonstrated that derivatives of 3-methoxybenzamide exhibit promising activity as selective herbicides, contributing to sustainable agricultural practices by controlling unwanted plant growth without harming the environment or food crops. These applications are particularly important in the context of integrated pest management strategies.

3-Methoxybenzamide also finds utility in the field of materials science. Its chemical structure, which contains both a methoxy group and an amide group, provides opportunities for designing novel polymer materials. The compound can act as a monomer or a cross-linking agent in the formation of polymers with specific mechanical, electrical, or optical properties. Research into the use of aromatic amides in materials science has led to advancements in the development of high-performance polymers used in various applications, including electronics, coatings, and sensors.

In conclusion, 3-methoxybenzamide is a versatile compound with a wide range of applications in pharmaceuticals, materials science, agrochemicals, and specialty chemicals. Its ability to serve as a building block for the synthesis of more complex molecules, coupled with its reactivity in various chemical processes, makes it an essential compound in both industrial and academic research. Ongoing studies of its bioactivity and potential uses in drug design, environmental management, and materials development continue to highlight its importance across multiple scientific fields.