4-Hydroxybenzaldehyde (123-08-: Properties, Applications, and Industrial Significance
4-Hydroxybenzaldehyde (CAS No. 123-08- is an important organic compound widely used in chemical synthesis, pharmaceutical production, and material science. It is a member of the aldehyde family, with a hydroxyl group (-OH) attached to the benzene ring in the para position relative to the formyl group (-CHO). This compound is valued for its unique chemical structure, which imparts a range of properties making it useful in various applications.
1. Introduction to 4-Hydroxybenzaldehyde (123-08-
4-Hydroxybenzaldehyde, also known as para-hydroxybenzaldehyde, is a pale yellow crystalline solid with the molecular formula C7H6O2. The compound features a benzene ring with a hydroxyl group (-OH) at the para position and an aldehyde group (-CHO) at the opposite site on the ring. Its structure allows it to act as an intermediate in various organic synthesis reactions, where the hydroxyl and aldehyde groups are critical for introducing functional groups into molecules.
4-Hydroxybenzaldehyde (123-08- is produced through several methods, including the oxidation of 4-hydroxybenzyl alcohol or through direct functionalization of aromatic compounds. Due to its versatility, it is used in the production of a wide range of chemicals, including pharmaceuticals, agrochemicals, and flavoring agents.
2. Chemical Properties of 4-Hydroxybenzaldehyde (123-08-
4-Hydroxybenzaldehyde (123-08- exhibits a range of chemical properties that make it highly useful in synthetic chemistry:
Functional Groups: The aldehyde group (-CHO) is reactive, enabling 4-Hydroxybenzaldehyde to undergo nucleophilic addition reactions and other transformations. The hydroxyl group (-OH) adds polarity to the compound, making it soluble in alcohols, ethers, and polar solvents.
Reactivity: As an aromatic aldehyde, 4-Hydroxybenzaldehyde is highly reactive in electrophilic aromatic substitution reactions. It can undergo Friedel-Crafts reactions, condensation reactions, and other processes to form various derivatives.
Oxidation and Reduction: The aldehyde group can undergo oxidation to form acids, or it can be reduced to form alcohols. The compound also participates in reactions that involve carbonyl chemistry, making it useful in the synthesis of more complex molecules.
Solubility: 4-Hydroxybenzaldehyde is soluble in ethanol, methanol, acetone, and other polar solvents. It is insoluble in non-polar solvents like hexane, which is typical for aromatic aldehydes.
Melting Point and Stability: The compound has a melting point of approximately 111-113°C, which makes it a stable, crystalline solid under standard conditions. It should be stored in a cool, dry place away from strong oxidizers.
These chemical properties make 4-Hydroxybenzaldehyde (123-08- a versatile reagent in synthetic organic chemistry.
3. Applications of 4-Hydroxybenzaldehyde (123-08-
4-Hydroxybenzaldehyde is used in a variety of applications across several industries, thanks to its chemical reactivity and versatile functional groups:
3.1 Pharmaceutical Industry
One of the most significant uses of 4-Hydroxybenzaldehyde (123-08- is as a building block in the pharmaceutical industry. It is used in the synthesis of various bioactive molecules:
Synthesis of Drugs: 4-Hydroxybenzaldehyde is used in the preparation of compounds with therapeutic effects, including anti-inflammatory, antimicrobial, and anticancer drugs. The aldehyde group can be reacted with amines and alcohols to create sulfonamides, amides, and other functionalized derivatives.
Flavonoid Synthesis: The compound is also an intermediate in the synthesis of flavonoids, which have diverse pharmacological activities, such as antioxidant, anti-inflammatory, and anticancer properties.
Drug Intermediates: 4-Hydroxybenzaldehyde (123-08- serves as a precursor for the synthesis of more complex pharmaceutical molecules, including those used to treat heart disease, infections, and metabolic disorders.
3.2 Agrochemical Industry
4-Hydroxybenzaldehyde plays a role in the agrochemical industry, where it is used in the production of herbicides, fungicides, and insecticides:
Synthesis of Agrochemicals: The aldehyde group in 4-Hydroxybenzaldehyde allows it to react with other functional groups to form active ingredients used in plant protection products.
Plant Growth Regulators: It is also used as a starting material for synthesizing plant growth regulators and herbicides that help control unwanted plant species or promote the growth of crops.
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