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.