4-Methoxy Benzaldehyde;4-Methoxybenzaldehyde
product_name 4-Methoxy Benzaldehyde
CAS_number 123-11-5
formula C8H8O2
molar_mass 136.15 g/mol
pub_chem_CID 31245
drug_bank DB03618
chem_spider 29005
bioavailability Not applicable
protein_binding Not applicable
metabolism Not applicable
elimination_halflife Not applicable


FAQ

What is 4-Methoxy Benzaldehyde, and where is it commonly used?


4-Methoxy Benzaldehyde, also known as 4-Anisaldehyde, is an organic compound characterized by the presence of a benzene ring substituted with a methoxy group (-OCH3) and an aldehyde group (-CHO) at the para position. This aromatic aldehyde is noteworthy for its pleasant, anisic (anise-like) scent, which makes it valuable in a range of applications. One of the most prominent uses of 4-Methoxy Benzaldehyde is in the fragrance industry, where it is utilized as a key ingredient in perfumes, soaps, and other scented products. Its sweet and mildly spicy fragrance adds a desirable note to many personal care items.

In addition to its olfactory uses, 4-Methoxy Benzaldehyde is also employed in the food and beverage industry as a flavoring agent. Its distinctive licorice and anise flavor can enhance the taste profiles of a variety of consumables, ranging from confectionery items to alcoholic beverages. This compound's ability to impart a warm, spicy flavor makes it a versatile additive in culinary contexts.

Beyond its sensory applications, 4-Methoxy Benzaldehyde serves an important role in organic synthesis. It is used as an intermediate in the production of various pharmaceuticals, dyes, and other chemical compounds. Its structural versatility allows it to participate in numerous chemical reactions, facilitating the manufacture of complex molecules used in medicine, agriculture, and industry. For instance, derivatives of 4-Methoxy Benzaldehyde are often utilized in the synthesis of antimicrobial agents and other therapeutic compounds, underscoring its significance in medicinal chemistry.

In summary, 4-Methoxy Benzaldehyde is a multifaceted compound with applications spanning from fragrances and flavors to organic synthesis. Its unique chemical and sensory properties make it a valuable ingredient in various industries, highlighting its importance as a versatile and essential chemical intermediate.

What are the chemical properties of 4-Methoxy Benzaldehyde?


4-Methoxy Benzaldehyde is a chemical compound with the molecular formula C8H8O2. Its molecular weight is approximately 136.15 g/mol. The structure of 4-Methoxy Benzaldehyde consists of a benzene ring that is para-substituted with a methoxy group (-OCH3) and an aldehyde group (-CHO). This specific positioning of functional groups significantly influences its chemical properties and reactivity.

One of the primary chemical properties of 4-Methoxy Benzaldehyde is its aromatic nature, which lends stability to the molecule through resonance. The methoxy group, being an electron-donating group, increases the electron density of the benzene ring, particularly at the ortho and para positions relative to itself. This enhanced electron density makes 4-Methoxy Benzaldehyde more reactive towards electrophilic aromatic substitution reactions, such as nitration or halogenation, when compared to benzaldehyde.

Furthermore, the aldehyde group in 4-Methoxy Benzaldehyde retains typical aldehyde reactivity, making it susceptible to nucleophilic addition reactions. For instance, it can readily participate in the formation of Schiff bases (imines) when reacted with primary amines. Additionally, it can form acetals and hemiacetals in the presence of alcohols and acid catalysts.

The presence of the methoxy group also impacts the compound's boiling and melting points. 4-Methoxy Benzaldehyde has a melting point of around 2-4°C and a boiling point of approximately 248°C. These physical properties are indicative of the compound's relatively low volatility at room temperature, making it manageable in various industrial applications without significant loss due to evaporation.

Solubility is another critical aspect of 4-Methoxy Benzaldehyde's chemical profile. It is moderately soluble in organic solvents such as ethanol, methanol, and ether, but has limited solubility in water due to the hydrophobic nature of the benzene ring. This solubility characteristic is advantageous in organic synthesis, where polar organic solvents are commonly used.

In summary, the chemical properties of 4-Methoxy Benzaldehyde are defined by its aromatic structure, electron-donating methoxy group, and reactive aldehyde functional group. These features contribute to its behavior in various chemical reactions and its suitability for applications in industries ranging from fragrance to pharmaceuticals.

How is 4-Methoxy Benzaldehyde synthesized?


The synthesis of 4-Methoxy Benzaldehyde can be achieved through several methods, depending on the availability of starting materials and the desired scale of production. One of the most common synthetic routes is the oxidation of 4-Methoxytoluene (p-cresyl methyl ether) to 4-Methoxy Benzaldehyde. This oxidation can be performed using a variety of oxidizing agents, such as potassium permanganate, chromium trioxide, or sodium dichromate.

In the laboratory setting, the oxidation of 4-Methoxytoluene is typically carried out using potassium permanganate in an alkaline medium. The reaction involves the oxidative cleavage of the methyl group, resulting in the formation of the aldehyde group. The general reaction mechanism proceeds through the formation of an intermediate manganese complex, followed by a series of electron transfer steps that lead to the final product, 4-Methoxy Benzaldehyde. After the reaction, the mixture is usually worked up by acidification and extraction to isolate the desired aldehyde.

Another synthetic approach involves the formylation of anisole (methoxybenzene) using the Vilsmeier-Haack reaction. This method involves the treatment of anisole with a Vilsmeier reagent, which is typically generated in situ from dimethylformamide (DMF) and either phosphorus oxychloride (POCl3) or thionyl chloride (SOCl2). The Vilsmeier reagent serves as a formylating agent that introduces the formyl group (-CHO) at the para position of anisole, yielding 4-Methoxy Benzaldehyde. This reaction is highly selective and efficient, making it suitable for both small-scale and industrial-scale synthesis.

In the context of green chemistry, catalytic methods for the synthesis of 4-Methoxy Benzaldehyde have been explored to minimize environmental impact. For instance, the use of catalytic systems based on palladium or copper has been investigated for the direct formylation of methoxyaromatic compounds under mild conditions. These catalytic processes often utilize benign reagents and solvents, reducing hazardous waste and improving overall sustainability.

Additionally, biocatalytic approaches have been developed, employing enzymes such as monooxygenases or peroxidases to facilitate the transformation of methoxytoluene derivatives into aldehydes. These enzymatic methods offer advantages in terms of specificity and environmental friendliness, though they may require optimization for large-scale application.

In summary, 4-Methoxy Benzaldehyde can be synthesized via several routes, including the oxidation of 4-Methoxytoluene, the Vilsmeier-Haack formylation of anisole, catalytic formylation methods, and biocatalytic transformations. Each method has its own set of advantages and limitations, and the choice of synthetic route depends on factors such as availability of starting materials, desired product yield, and environmental considerations.

What are the safety considerations when handling 4-Methoxy Benzaldehyde?


Handling 4-Methoxy Benzaldehyde requires careful attention to safety due to its chemical properties and potential health hazards. While it is generally considered to have a low toxicity compared to some other aromatic aldehydes, proper safety protocols must still be followed to minimize risks.

First and foremost, appropriate personal protective equipment (PPE) should always be worn when handling 4-Methoxy Benzaldehyde. This includes gloves, safety goggles, and lab coats to protect the skin and eyes from potential contact with the compound. In some cases, a fume hood or respirator may be necessary to protect against inhalation of vapors, especially in situations where the compound is being heated or used in large quantities.

4-Methoxy Benzaldehyde can cause skin and eye irritation upon contact, and its vapors may irritate the respiratory tract. Therefore, it is essential to work in a well-ventilated area to avoid inhalation of fumes. In the event of skin contact, the affected area should be washed immediately with plenty of water and soap. If the compound comes into contact with the eyes, they should be rinsed thoroughly with water for at least 15 minutes, and medical attention should be sought if irritation persists.

Proper storage of 4-Methoxy Benzaldehyde is also crucial for safety. The compound should be stored in a tightly sealed container, away from direct sunlight, heat sources, and incompatible chemicals such as strong oxidizing agents. It is advisable to keep it in a cool, dry, and well-ventilated area to prevent degradation and the buildup of vapors.

In the case of a spill, it is important to contain and clean it up promptly to prevent exposure and environmental contamination. Small spills can be absorbed using an inert material such as vermiculite or sand, and the waste should be disposed of according to local regulations for hazardous materials. For larger spills, professional assistance may be required to manage the cleanup process safely.

When working with 4-Methoxy Benzaldehyde, it is also important to be aware of its potential reactivity. Although it is stable under normal conditions, contact with strong oxidizers or reducing agents can result in hazardous reactions. Therefore, mixing it with incompatible substances should be avoided, and any experimental procedures involving reactive chemicals should be conducted with appropriate safeguards in place.

In summary, the safe handling of 4-Methoxy Benzaldehyde involves the use of personal protective equipment, proper storage, working in a well-ventilated environment, and prompt management of spills. By adhering to these safety considerations, the risks associated with handling this compound can be minimized, ensuring a safe working environment.

Can 4-Methoxy Benzaldehyde be used in green chemistry?


4-Methoxy Benzaldehyde can indeed be incorporated into green chemistry practices, aligning with the principles aimed at reducing environmental impact and enhancing sustainability. Green chemistry seeks to design chemical processes and products that minimize the use and generation of hazardous substances, enhance energy efficiency, and utilize renewable resources when possible.

One of the primary ways 4-Methoxy Benzaldehyde can be used in green chemistry is through the development of eco-friendly synthetic routes. Traditional synthesis methods often involve hazardous reagents and produce significant waste. However, innovative approaches utilizing catalytic reactions, biocatalysis, and greener solvents can mitigate these issues. For instance, catalytic formylation reactions using palladium or copper catalysts in place of stoichiometric reagents can reduce waste and improve atom economy. Additionally, using water or other benign solvents instead of volatile organic solvents (VOCs) can further decrease the environmental footprint.

Biocatalytic synthesis involving enzymes like monooxygenases or peroxidases represents another green approach. Enzymatic processes typically operate under mild conditions (ambient temperature and pressure) and use water as a solvent. This reduces energy consumption and eliminates the need for harmful reagents. Moreover, enzymes are highly selective, often resulting in fewer by-products and higher yields, which aligns with the green chemistry goal of maximizing efficiency and reducing waste.

Another aspect of green chemistry involves the application of 4-Methoxy Benzaldehyde in the production of environmentally friendly products. For example, in the fragrance industry, synthetic fragrances derived from 4-Methoxy Benzaldehyde can replace natural extracts that might be sourced unsustainably from plants. This substitution can help preserve biodiversity and reduce deforestation associated with harvesting natural aromatic compounds.

Furthermore, 4-Methoxy Benzaldehyde can be used as an intermediate in the synthesis of greener polymers and biodegradable materials. By leveraging its reactivity, sustainable polymers with minimal environmental impact can be designed. These polymers could potentially replace conventional plastics, reducing the reliance on petroleum-based resources and mitigating plastic pollution.

Lifecycle analysis (LCA) is another tool of green chemistry that can be applied to assess the environmental impact of 4-Methoxy Benzaldehyde throughout its lifecycle—from raw material extraction to disposal. By understanding the environmental footprint, strategies can be developed to minimize adverse effects. This might include optimizing synthetic routes to reduce energy consumption and emissions, improving yield to decrease waste, and developing methods to recycle or safely dispose of by-products.

Finally, 4-Methoxy Benzaldehyde's potential use in pharmaceuticals can be aligned with green chemistry principles by employing sustainable practices in drug development and manufacturing. Green medicinal chemistry focuses on reducing the environmental impact of drug synthesis while maintaining efficacy and safety. This includes using alternative solvents, optimizing reaction conditions, and minimizing the number of synthetic steps.

In summary, 4-Methoxy Benzaldehyde can be utilized in green chemistry through eco-friendly synthesis methods, its application in sustainable products, lifecycle analysis, and green practices in pharmaceuticals. By embracing these green chemistry principles, the environmental and health impacts associated with the use of 4-Methoxy Benzaldehyde can be significantly reduced, contributing to a more sustainable future.
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