{"id":3448,"date":"2024-07-12T06:47:26","date_gmt":"2024-07-12T06:47:26","guid":{"rendered":"https:\/\/pharm.sinocurechem.com\/?p=3448"},"modified":"2024-07-12T06:47:26","modified_gmt":"2024-07-12T06:47:26","slug":"4-hydroxybenzaldehyde-structure-synthesis-applications-and-safety","status":"publish","type":"post","link":"https:\/\/longchangextracts.com\/da\/4-hydroxybenzaldehyde-structure-synthesis-applications-and-safety\/","title":{"rendered":"4-Hydroxybenzaldehyd: Struktur, syntese, anvendelse og sikkerhed"},"content":{"rendered":"

1. <\/span>Chemical Structure and Properties<\/span><\/b><\/p>\n

Molecular Structure<\/span><\/p>\n

4-Hydroxybenzaldehyde, also known as p-hydroxybenzaldehyde, has a benzene ring with two functional groups:<\/span><\/p>\n

A hydroxyl group (-OH) at the para position (carbon 4).<\/span><\/p>\n

An aldehyde group (-CHO) at the para position relative to the hydroxyl group.<\/span><\/p>\n

The structural formula can be represented as:<\/span><\/p>\n

\u00a0\u00a0\u00a0\u00a0OH<\/span><\/p>\n

\u00a0\u00a0\u00a0\u00a0\u00a0|<\/span><\/p>\n

\u00a0\u00a0C6H4<\/span><\/p>\n

\u00a0\u00a0\u00a0\u00a0\u00a0|<\/span><\/p>\n

\u00a0\u00a0\u00a0CHO<\/span><\/p>\n

This positioning gives 4-Hydroxybenzaldehyde its unique reactivity profile.<\/span><\/p>\n

Physical Properties<\/span><\/p>\n

Appearance: White to light yellow crystalline powder.<\/span><\/p>\n

Molecular Formula: C7H6O2.<\/span><\/p>\n

Molecular Weight: 122.12 g\/mol.<\/span><\/p>\n

Melting Point: 115-118 \u00b0C. The melting point indicates the temperature at which the solid form of 4-Hydroxybenzaldehyde transitions to a liquid state.<\/span><\/p>\n

Boiling Point: 191-192 \u00b0C. This is the temperature at which 4-Hydroxybenzaldehyde transitions from a liquid to a gaseous state.<\/span><\/p>\n

Density: 1.226 g\/cm\u00b3. This property describes the mass per unit volume of 4-Hydroxybenzaldehyde.<\/span><\/p>\n

Refractive Index: 1.579. This indicates how light propagates through the compound.<\/span><\/p>\n

Solubility<\/span><\/p>\n

Water Solubility: Slightly soluble. The hydroxyl group increases solubility in water compared to other benzaldehydes.<\/span><\/p>\n

Organic Solvents: Soluble in ethanol, ether, and chloroform. This high solubility in organic solvents makes it versatile for use in organic synthesis.<\/span><\/p>\n

Spectroscopic Properties<\/span><\/p>\n

UV-Vis Spectroscopy: Shows characteristic absorption peaks due to the aromatic ring and conjugated system.<\/span><\/p>\n

IR Spectroscopy:<\/span><\/p>\n

Broad band around 3200-3600 cm\u207b\u00b9 due to O-H stretching vibrations.<\/span><\/p>\n

Strong peak around 1680-1700 cm\u207b\u00b9 due to the C=O stretching vibration of the aldehyde group.<\/span><\/p>\n

Peaks in the region of 1400-1600 cm\u207b\u00b9 corresponding to C=C stretching vibrations of the benzene ring.<\/span><\/p>\n

NMR Spectroscopy:<\/span><\/p>\n

Proton NMR (\u00b9H NMR): The aldehyde proton appears as a singlet around 9-10 ppm. The aromatic protons typically appear in the range of 6-8 ppm, with the hydroxyl proton appearing around 4-5 ppm.<\/span><\/p>\n

Carbon-13 NMR (\u00b9\u00b3C NMR): The aldehyde carbon shows a peak around 190-200 ppm, and aromatic carbons appear in the range of 110-160 ppm.<\/span><\/p>\n

Chemical Reactivity<\/span><\/p>\n

Aldehyde Reactivity: The -CHO group can participate in nucleophilic addition reactions, oxidation to carboxylic acids, and reduction to alcohols.<\/span><\/p>\n

Hydroxyl Reactivity: The -OH group can undergo typical phenolic reactions, including esterification, etherification, and electrophilic aromatic substitution.<\/span><\/p>\n

Electrophilic Aromatic Substitution: The hydroxyl group activates the benzene ring towards electrophilic aromatic substitution, particularly at the ortho and para positions relative to the hydroxyl group.<\/span><\/p>\n

Stability<\/span><\/p>\n

4-Hydroxybenzaldehyde is relatively stable under normal conditions but should be stored in a cool, dry place away from strong oxidizing agents. Exposure to light and air can lead to gradual oxidation and degradation, affecting its purity and efficacy.<\/span><\/p>\n

Derivatives<\/span><\/p>\n

4-Hydroxybenzaldehyde can be chemically modified to produce various derivatives:<\/span><\/p>\n

4-Hydroxybenzoic Acid: Through oxidation of the aldehyde group.<\/span><\/p>\n

4-Methoxybenzaldehyde: By methylation of the hydroxyl group.<\/span><\/p>\n

Schiff Bases: Formed by condensation with amines.<\/span><\/p>\n

These derivatives expand the utility of 4-Hydroxybenzaldehyde in different applications, including pharmaceuticals, fragrances, and organic synthesis.<\/span><\/p>\n

2.\u00a0<\/span>Synthesis of 4-Hydroxybenzaldehyde<\/span><\/b><\/b><\/p>\n

4-Hydroxybenzaldehyde can be synthesized through several methods, each with its advantages depending on the required purity, yield, and specific application. Here are some common synthesis methods:<\/span><\/p>\n

1)\u00a0<\/span>Oxidation of 4-Hydroxytoluene (p-Cresol)<\/span><\/b><\/b><\/p>\n

One of the most straightforward methods involves the oxidation of 4-hydroxytoluene:<\/span><\/p>\n

Starting Material: p-Cresol (4-hydroxytoluene).<\/span><\/p>\n

Oxidizing Agents: Common oxidizing agents include potassium permanganate (KMnO\u2084), chromium trioxide (CrO\u2083), or manganese dioxide (MnO\u2082).<\/span><\/p>\n

Procedure:<\/span><\/p>\n

Dissolve p-cresol in an appropriate solvent, such as water or a mixture of water and an organic solvent.<\/span><\/p>\n

Add the oxidizing agent slowly while maintaining the reaction temperature.<\/span><\/p>\n

Stir the reaction mixture until the oxidation is complete.<\/span><\/p>\n

Filter the mixture to remove any precipitate and purify the product through recrystallization or distillation.<\/span><\/p>\n

2)\u00a0<\/span>Hydrolysis of 4-Hydroxybenzyl Alcohol<\/span><\/b><\/b><\/p>\n

Hydrolysis of 4-hydroxybenzyl alcohol is another method to obtain 4-Hydroxybenzaldehyde:<\/span><\/p>\n

Starting Material: 4-Hydroxybenzyl alcohol.<\/span><\/p>\n

Reagents: Aqueous acid solution (such as hydrochloric acid, HCl) or catalytic amount of an acid.<\/span><\/p>\n

Procedure:<\/span><\/p>\n

Dissolve 4-hydroxybenzyl alcohol in an acid solution.<\/span><\/p>\n

Heat the mixture under reflux.<\/span><\/p>\n

After the reaction is complete, cool the mixture and extract the product.<\/span><\/p>\n

Purify 4-Hydroxybenzaldehyde by recrystallization.<\/span><\/p>\n

3)\u00a0<\/span>Purification<\/span><\/b><\/b><\/p>\n

After the synthesis, 4-Hydroxybenzaldehyde is typically purified to obtain the desired level of purity:<\/span><\/p>\n

Recrystallization: Dissolve the crude product in a minimal amount of hot solvent (e.g., ethanol or water) and allow it to cool slowly. Crystals of pure 4-Hydroxybenzaldehyde will form.<\/span><\/p>\n

Distillation: For purification through distillation, vacuum distillation can be used to avoid decomposition at high temperatures.<\/span><\/p>\n

Chromatography: Column chromatography can be employed for further purification if required.<\/span><\/p>\n

3.\u00a0<\/span>Applications of 4-Hydroxybenzaldehyde<\/span><\/b><\/b><\/p>\n

1)\u00a0<\/span>Pharmaceuticals<\/span><\/b><\/b><\/p>\n

Intermediate in Drug Synthesis:<\/span><\/p>\n

4-Hydroxybenzaldehyde serves as a key intermediate in the synthesis of several pharmaceutical compounds.<\/span><\/p>\n

It is used in the production of antihypertensive agents, anti-inflammatory drugs, and antimicrobial compounds. For instance, it is a precursor in the synthesis of 4-Hydroxyphenylglycine, which is used in the manufacture of certain antibiotics.<\/span><\/p>\n

Analytical Reagent:<\/span><\/p>\n

It is employed as a derivatizing agent in analytical chemistry for the quantitative determination of various pharmaceutical substances.<\/span><\/p>\n

Its ability to form Schiff bases with amines makes it useful in the detection and analysis of amino-containing drugs.<\/span><\/p>\n

2)\u00a0<\/span>2. Flavors and Fragrances<\/span><\/b><\/b><\/p>\n

Aroma Compound:<\/span><\/p>\n

4-Hydroxybenzaldehyde is utilized as a flavoring agent in the food industry due to its pleasant almond-like odor.<\/span><\/p>\n

It is a component in the formulation of various fragrances used in perfumes, soaps, and cosmetics.<\/span><\/p>\n

Synthesis of Vanillin:<\/span><\/p>\n

It is an important intermediate in the synthesis of vanillin (4-Hydroxy-3-methoxybenzaldehyde), one of the most popular flavoring agents used in food products, beverages, and pharmaceuticals.<\/span><\/p>\n

3)\u00a0<\/span>Organic Synthesis<\/span><\/b><\/b><\/p>\n

Building Block:<\/span><\/p>\n

4-Hydroxybenzaldehyde is a valuable building block in organic synthesis, contributing to the construction of more complex molecules.<\/span><\/p>\n

It is used in the synthesis of heterocyclic compounds, which have applications in pharmaceuticals and agrochemicals.<\/span><\/p>\n

Cross-Coupling Reactions:<\/span><\/p>\n

It participates in Suzuki and Heck coupling reactions, facilitating the formation of carbon-carbon bonds essential in the synthesis of biaryl compounds and other complex structures.<\/span><\/p>\n

4)\u00a0<\/span>Biological Research<\/span><\/b><\/b><\/p>\n

Enzyme Inhibition Studies:<\/span><\/p>\n

4-Hydroxybenzaldehyde is used in biochemical research to study the inhibition of specific enzymes.<\/span><\/p>\n

It helps in understanding enzyme function and regulation, which is crucial for drug development and therapeutic interventions.<\/span><\/p>\n

Antioxidant Research:<\/span><\/p>\n

It is investigated for its antioxidant properties, contributing to studies on oxidative stress and related diseases.<\/span><\/p>\n

Its ability to scavenge free radicals makes it a candidate for research in the prevention and treatment of conditions associated with oxidative damage.<\/span><\/p>\n

5)\u00a0<\/span>Polymer Industry<\/span><\/b><\/b><\/p>\n

Polymer Additive:<\/span><\/p>\n

It is used as a precursor in the synthesis of phenolic resins and other polymeric materials.<\/span><\/p>\n

These polymers are employed in coatings, adhesives, and composite materials, offering enhanced mechanical and thermal properties.<\/span><\/p>\n

Stabilizers:<\/span><\/p>\n

4-Hydroxybenzaldehyde can act as a stabilizer in the polymerization processes, improving the stability and performance of the final polymer products.<\/span><\/p>\n

6)\u00a0<\/span>Agrochemicals<\/span><\/b><\/b><\/p>\n

Pesticides and Herbicides:<\/span><\/p>\n

It is a precursor in the synthesis of various agrochemicals, including pesticides and herbicides.<\/span><\/p>\n

These compounds are crucial for pest control and improving agricultural productivity.<\/span><\/p>\n

7)\u00a0<\/span>Dyes and Pigments<\/span><\/b><\/b><\/p>\n

Synthesis of Dyes:<\/span><\/p>\n

It is used in the production of azo dyes and other colorants.<\/span><\/p>\n

These dyes find applications in textiles, inks, and coatings, providing vibrant and durable colors.<\/span><\/p>\n

4.\u00a0<\/span>Safety and Handling<\/span><\/b><\/b><\/p>\n

May cause skin and eye irritation; harmful if swallowed or inhaled.<\/span><\/p>\n

Use gloves, safety goggles, and lab coats to prevent contact.<\/span><\/p>\n

Store in a cool, dry place away from incompatible substances such as strong oxidizers.<\/span><\/p>\n","protected":false},"excerpt":{"rendered":"

1. Chemical Structure and Properties Molecular Structure 4-Hydroxybenzaldehyde, also known as p-hydroxybenzaldehyde, has a benzene ring with two functional groups: A hydroxyl group (-OH) at the para position (carbon 4). An aldehyde group (-CHO) at the para position relative to the hydroxyl group. The structural formula can be represented as: \u00a0\u00a0\u00a0\u00a0OH \u00a0\u00a0\u00a0\u00a0\u00a0| \u00a0\u00a0C6H4 \u00a0\u00a0\u00a0\u00a0\u00a0| \u00a0\u00a0\u00a0CHO […]<\/p>\n","protected":false},"author":1,"featured_media":0,"comment_status":"closed","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[20],"tags":[],"yoast_head":"\n4-Hydroxybenzaldehyde: Structure, Synthesis, Applications, and Safety - China Chemical Manufacturer<\/title>\n<meta name=\"robots\" content=\"index, follow, max-snippet:-1, max-image-preview:large, max-video-preview:-1\" \/>\n<link rel=\"canonical\" href=\"https:\/\/longchangextracts.com\/da\/4-hydroxybenzaldehyde-structure-synthesis-applications-and-safety\/\" \/>\n<meta property=\"og:locale\" content=\"da_DK\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"4-Hydroxybenzaldehyde: Structure, Synthesis, Applications, and Safety - China Chemical Manufacturer\" \/>\n<meta property=\"og:description\" content=\"1. Chemical Structure and Properties Molecular Structure 4-Hydroxybenzaldehyde, also known as p-hydroxybenzaldehyde, has a benzene ring with two functional groups: A hydroxyl group (-OH) at the para position (carbon 4). An aldehyde group (-CHO) at the para position relative to the hydroxyl group. The structural formula can be represented as: \u00a0\u00a0\u00a0\u00a0OH \u00a0\u00a0\u00a0\u00a0\u00a0| \u00a0\u00a0C6H4 \u00a0\u00a0\u00a0\u00a0\u00a0| \u00a0\u00a0\u00a0CHO […]\" \/>\n<meta property=\"og:url\" content=\"https:\/\/longchangextracts.com\/da\/4-hydroxybenzaldehyde-structure-synthesis-applications-and-safety\/\" \/>\n<meta property=\"og:site_name\" content=\"China Chemical Manufacturer\" \/>\n<meta property=\"article:published_time\" content=\"2024-07-12T06:47:26+00:00\" \/>\n<meta name=\"author\" content=\"Longchang Chemical\" \/>\n<meta name=\"twitter:card\" content=\"summary_large_image\" \/>\n<meta name=\"twitter:label1\" content=\"Skrevet af\" \/>\n\t<meta name=\"twitter:data1\" content=\"Longchang Chemical\" \/>\n\t<meta name=\"twitter:label2\" content=\"Estimeret l\u00e6setid\" \/>\n\t<meta name=\"twitter:data2\" content=\"6 minutter\" \/>\n<script type=\"application\/ld+json\" class=\"yoast-schema-graph\">{\"@context\":\"https:\/\/schema.org\",\"@graph\":[{\"@type\":\"WebPage\",\"@id\":\"https:\/\/longchangextracts.com\/4-hydroxybenzaldehyde-structure-synthesis-applications-and-safety\/\",\"url\":\"https:\/\/longchangextracts.com\/4-hydroxybenzaldehyde-structure-synthesis-applications-and-safety\/\",\"name\":\"4-Hydroxybenzaldehyde: Structure, Synthesis, Applications, and Safety - China Chemical Manufacturer\",\"isPartOf\":{\"@id\":\"https:\/\/longchangextracts.com\/#website\"},\"datePublished\":\"2024-07-12T06:47:26+00:00\",\"dateModified\":\"2024-07-12T06:47:26+00:00\",\"author\":{\"@id\":\"https:\/\/longchangextracts.com\/#\/schema\/person\/80933ac6926ad63fea74ec33f8d04869\"},\"breadcrumb\":{\"@id\":\"https:\/\/longchangextracts.com\/4-hydroxybenzaldehyde-structure-synthesis-applications-and-safety\/#breadcrumb\"},\"inLanguage\":\"da-DK\",\"potentialAction\":[{\"@type\":\"ReadAction\",\"target\":[\"https:\/\/longchangextracts.com\/4-hydroxybenzaldehyde-structure-synthesis-applications-and-safety\/\"]}]},{\"@type\":\"BreadcrumbList\",\"@id\":\"https:\/\/longchangextracts.com\/4-hydroxybenzaldehyde-structure-synthesis-applications-and-safety\/#breadcrumb\",\"itemListElement\":[{\"@type\":\"ListItem\",\"position\":1,\"name\":\"Home\",\"item\":\"https:\/\/longchangextracts.com\/\"},{\"@type\":\"ListItem\",\"position\":2,\"name\":\"4-Hydroxybenzaldehyde: Structure, Synthesis, Applications, and Safety\"}]},{\"@type\":\"WebSite\",\"@id\":\"https:\/\/longchangextracts.com\/#website\",\"url\":\"https:\/\/longchangextracts.com\/\",\"name\":\"China Chemical Manufacturer\",\"description\":\"\",\"potentialAction\":[{\"@type\":\"SearchAction\",\"target\":{\"@type\":\"EntryPoint\",\"urlTemplate\":\"https:\/\/longchangextracts.com\/?s={search_term_string}\"},\"query-input\":\"required name=search_term_string\"}],\"inLanguage\":\"da-DK\"},{\"@type\":\"Person\",\"@id\":\"https:\/\/longchangextracts.com\/#\/schema\/person\/80933ac6926ad63fea74ec33f8d04869\",\"name\":\"Longchang Chemical\",\"image\":{\"@type\":\"ImageObject\",\"inLanguage\":\"da-DK\",\"@id\":\"https:\/\/longchangextracts.com\/#\/schema\/person\/image\/\",\"url\":\"https:\/\/secure.gravatar.com\/avatar\/c1e84ee0759373263198c58e8f338f80?s=96&d=mm&r=g\",\"contentUrl\":\"https:\/\/secure.gravatar.com\/avatar\/c1e84ee0759373263198c58e8f338f80?s=96&d=mm&r=g\",\"caption\":\"Longchang Chemical\"},\"description\":\"Longchang Chemical is the company publisher of chemical, ingredient and technical procurement information on longchangextracts.com. 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