4-Hydroxybenzhydrazide is an organic compound with CAS 5351-23-5 and molecular formula C15H14N2O3. It is a white to light yellow solid powder. The melting point range of this compound is usually between 180-183 ° C. Its relatively high melting point indicates that it can only transition from solid to liquid at higher temperatures. Stable at room temperature and pressure, but may decompose at high temperatures and exposure to light. Its stability is also affected by moisture, oxygen, and other factors. The molecular structure contains groups such as benzene ring, hydrazine group, and hydroxyl group, and the interaction between these groups affects their physical properties. The viscosity is usually low, indicating weak intermolecular interactions. It can be used as a functional material in fields such as electrochemical devices and optoelectronic materials. For example, it can be used as an electrode material for the manufacturing of secondary batteries or as an optoelectronic material for the manufacturing of optoelectronic devices. In addition to the above purposes, it can also be used in the fields of synthetic fragrances, surfactants, oilfield chemicals, etc. In addition, it can also be used as an additive in the manufacturing of certain special fibers.
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Chemical Formula |
C7H8N2O2 |
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Exact Mass |
152.06 |
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Molecular Weight |
152.15 |
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m/z |
152.06 (100.0%), 153.06 (7.6%) |
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Elemental Analysis |
C, 55.26; H, 5.30; N, 18.41; O, 21.03 |
Analytical Chemistry
One of the primary applications of 4-Hydroxybenzhydrazide is in analytical chemistry, particularly in the analysis of carbohydrates and enzymes. It is used for the determination of maltose concentrations in starch digestion processes and for analyzing fructans in food hydrolysates. PAHBAH is also utilized in the analysis of α-amylase and glucoamylase activities, as it enables a non-specific colorimetric assay to measure free reducing sugar groups in samples at a wavelength of 415 nm.
PAHBAH is used for the accurate determination of maltose concentrations in starch digestion processes. This is crucial in understanding the efficiency of starch breakdown and the subsequent release of sugars, such as maltose, during digestion. By quantifying maltose levels, researchers and industry professionals can assess the activity of enzymes involved in starch digestion and optimize processes accordingly.
Another important application of PAHBAH is in the analysis of fructans in food hydrolysates. Fructans are a type of carbohydrate found in many plants, including onions, garlic, and artichokes. By using PAHBAH, scientists can quantify the amount of fructans present in food samples, which is valuable information for food manufacturers and nutritionists.
PAHBAH is also utilized in the analysis of α-amylase and glucoamylase activities. These enzymes are responsible for breaking down starch into smaller sugars, such as maltose and glucose. By using PAHBAH, researchers can perform a non-specific colorimetric assay to measure the amount of free reducing sugar groups present in samples. This assay is based on the reaction between PAHBAH and reducing sugars, which results in a color change that can be quantified spectrophotometrically at a wavelength of 415 nm.
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Tobacco Industry
It is used in the tobacco industry, where it is employed for its specific chemical properties that contribute to the overall quality and characteristics of tobacco products. Its use in this industry highlights its versatility and adaptability to different applications.
- Chemical Enhancement: It is employed in tobacco products due to its unique chemical properties that can modify the taste, aroma, or burning characteristics of tobacco. It may interact with other components in tobacco to create desired sensory effects.
- Quality Improvement: By incorporating it, tobacco manufacturers can potentially improve the consistency and quality of their products. This could lead to a more satisfying consumer experience and increased product appeal.
- Process Optimization: The compound may also be used in the manufacturing process to optimize certain steps, such as curing or blending, which can further enhance the final product's attributes.
Other Potential Applications
While the above applications are well-documented, it may also have potential uses in other industries such as cosmetics, food additives, and materials science. Its properties as a hydroxyl-containing compound suggest it could be used in formulations where hydration, stability, or specific chemical interactions are desired.
Cosmetics Industry
Moisturizing Agents
The hydroxyl group can participate in hydrogen bonding, making it a potential ingredient in moisturizing formulations. It could help retain moisture in the skin, contributing to a hydrating effect in cosmetic products such as creams, lotions, and serums.
Stabilizers
The compound's ability to form stable chemical interactions could make it useful as a stabilizer in cosmetic formulations, helping to prevent the degradation of active ingredients and extend the shelf life of products.
Functional Ingredients
It could be explored as a functional ingredient in cosmetic products, such as those targeting specific skin concerns like anti-aging or skin brightening, by leveraging its chemical properties to enhance the efficacy of other active components.
Food Additives Industry
Flavor Enhancers
The compound's chemical structure might allow it to interact with taste receptors or other flavor components, potentially enhancing the flavor profile of food products. However, extensive safety and efficacy studies would be required before its use as a food additive.
Antioxidants
The hydroxyl group could confer antioxidant properties, making it a potential candidate for use as a natural antioxidant in food preservation to extend shelf life and maintain quality.
Stabilizers in Food Formulations
Similar to its potential use in cosmetics, it could act as a stabilizer in food formulations, helping to maintain the texture, consistency, and stability of food products.
Materials Science
Polymers and Coatings
The compound's reactivity and ability to form hydrogen bonds could make it useful in the synthesis of polymers and coatings with specific properties, such as improved adhesion, flexibility, or resistance to environmental factors.
Functional Materials
It could be incorporated into functional materials, such as sensors or actuators, where its chemical properties can be leveraged to achieve desired performance characteristics.
Nanomaterials
The compound's structure might allow it to be used in the synthesis or modification of nanomaterials, contributing to the development of new materials with unique properties and applications.
synthesis methods
Method 1: Using acetophenone as raw material
- Step 1: Mix acetophenone with hydrazine hydrate, add an appropriate amount of catalyst, and react at a suitable temperature for a period of time to generate phenylhydrazine.
- Step 2: React the generated phenylhydrazine with sulfuric acid to generate sulfate of p-hydroxybenzoic acid.
- Step 3: Neutralize the obtained sulfate with alkali to obtain p-hydroxybenzoic acid.
- Step 4: Mix p-hydroxybenzoic acid with ammonium chloride, add an appropriate amount of catalyst, and react at a suitable temperature for a period of time to generate 4 Hydroxybenzhydrazide.
The advantages of this method are simple operation, mild reaction conditions, and easy control. However, this method requires the use of a large amount of organic solvents and acid-base reagents, which can cause certain environmental pollution. In addition, this method requires multiple reactions to obtain the target product, with a relatively low yield.
Method 2: Using phenol as raw material
- Step 1: Mix phenol with ammonium chloride, add an appropriate amount of catalyst, and react at a suitable temperature for a period of time to generate p-hydroxybenzonitrile.
- Step 2: Mix the obtained p-hydroxybenzonitrile with hydrazine hydrate, add an appropriate amount of catalyst, and react at a suitable temperature for a period of time to generate p-hydroxybenzoyl hydrazine.
- Step 3: Hydrolyze p-hydroxybenzoyl hydrazine with dilute acid to obtain 4-Hydroxybenzhydrazide.
The advantage of this method is that the reaction conditions are mild and easy to control. However, this method requires multiple reactions to obtain the target product, and the yield is relatively low. In addition, this method requires the use of a large amount of organic solvents and acid-base reagents, which can cause certain environmental pollution.
It should be noted that both of the above methods are laboratory scale synthesis methods, which may require improvement and optimization for industrial production. In addition, specific synthesis conditions and reagent ratios also need to be adjusted and optimized according to the actual situation.
4-Hydroxybenzhydrazide, also known as 4-hydroxybenzoic acid hydrazide, is a chemical compound with the CAS number 5351-23-5. Its research and development history is rooted in its versatile applications across various industries, including pharmaceuticals, food, and cosmetics.
Initially, research focused on its synthesis and characterization. This compound is typically synthesized through the condensation reaction of 4-hydroxybenzoic acid with hydrazine. Early studies explored different reaction conditions and catalysts to optimize the yield and purity of the product. The compound's unique chemical structure, featuring a hydroxyl group and a hydrazide moiety, makes it a valuable intermediate in organic synthesis.
As research progressed, the pharmaceutical industry recognized the potential as a key intermediate in the synthesis of various drugs. Its ability to participate in various chemical reactions, such as nucleophilic substitutions and cyclization reactions, makes it an essential building block for the development of new therapeutic agents. Studies have investigated its role in the synthesis of anti-inflammatory drugs, antibiotics, and other pharmaceuticals.
In addition to its pharmaceutical applications, it has also been studied for its use in the food and cosmetic industries. As a food additive, it serves as a flavor enhancer and preservative. Its ability to produce a maple syrup-like aroma when heated with glucose has made it a popular ingredient in various food products. In cosmetics, it is used as a skin nutrient and moisturizer, thanks to its role as a component of the natural moisturizing factor (NMF) in the skin.
Recent research has also explored the potential in environmental and materials science. Its unique chemical properties make it a candidate for the development of new materials with specific functionalities, such as biodegradable polymers and advanced composites.
Throughout its research and development history, 4-hydroxybenzhydrazide has proven to be a versatile and valuable compound with a wide range of applications. Ongoing research continues to explore its potential in new areas, further expanding its utility and importance in various industries.
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