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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.
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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 |
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.
4-hydroxybenzoyl hydrazine, as an important organic compound, has demonstrated extensive application value in multiple fields.
As an analytical reagent
Determination of maltose concentration in starch digestion: It can be used to analyze the concentration of maltose during starch digestion, providing an important analytical tool for food science and nutrition research.
Analyzing the sugar content in pectin containing food hydrolysis products: In the food industry, pectin is an important dietary fiber, and the analysis of its sugar content is crucial for product quality control. Can be effectively used in this analysis process to ensure the stability and safety of the product.
Colorimetric determination of reducing sugars in processed feed: In the feed industry, the content of reducing sugars is one of the important factors affecting feed quality. Through colorimetric measurement, the content of reducing sugars in processed feed can be quickly and accurately determined, providing strong support for the quality control of feed.
Analyzing the activity of alpha amylase and glucose amylase: It can also be used to analyze the activity of alpha amylase and glucose amylase.
These two enzymes have important application value in the food industry, such as improving baked goods such as bread and biscuits. By measuring the activity of these two enzymes, the production process can be optimized and product quality can be improved.
Non specific colorimetric determination of free reducing sugar groups: Based on its analytical method, it is possible to non specifically colorimetric determine the free reducing sugar groups present in the sample, which plays an important role in quality control in industries such as food and beverage.
As an intermediate in organic synthesis
Synthesis of acylhydrazone compounds: It is an important intermediate for the synthesis of acylhydrazone compounds. Acyl hydrazone compounds have unique chemical structures and biological activities, and have broad application prospects in fields such as medicine and pesticides. For example, 4-hydroxy-2 '- (5-nitrofuran methylene) - benzoyl hydrazine, a potentially biologically active acylhydrazone compound, can be synthesized through the condensation reaction of 4-hydroxybenzoyl hydrazine with 5-nitrofurfural.
A new reagent for synthesizing aromatic acylhydrazones: It can also be used to synthesize a new reagent for 8-hydroxyquinoline-7-aldehyde aromatic acylhydrazones. This type of reagent has important application value in fields such as fluorescent probes and chemical sensing. For example, by reacting 4-hydroxybenzoyl hydrazine with 8-hydroxyquinoline-7-aldehyde, 8-hydroxyquinoline-7-aldehyde-p-hydroxybenzoyl hydrazone can be synthesized. This is a new reagent with fluorescent properties that can be used for the detection and analysis of metal ions.
Synthetic fluorescent probes: also play an important role in the synthesis of fluorescent probes. For example, the ligand 2,6-diacetylpyridine 4-hydroxybenzoyl hydrazine can be synthesized by reacting 4-hydroxybenzoyl hydrazine with 2,6-diacetylpyridine, and then reacted with RuCl 3 to prepare a ruthenium fluorescent probe. This fluorescent probe has potential application value in the preparation of anti-tumor drugs and tumor detection agents.
Application in the tobacco industry
It also has certain applications in the tobacco industry. Although its specific use may vary depending on the type and processing technology of tobacco products, it is generally believed that it may be used as a tobacco additive or improver to improve the taste, aroma, or combustion performance of tobacco. However, due to the particularity and sensitivity of the tobacco industry, there is currently relatively little publicly available research data on the specific applications and effects of tobacco.
As an industrial raw material
Used for industrial production: As an important industrial raw material, it is widely used in various industries such as electronics, chemistry, coatings, hardware, plastics, machinery, electroplating, and sewage treatment. Its unique chemical properties and stability make it an indispensable raw material in these industries.
Preparation of other organic compounds: In addition to the synthetic applications mentioned above, it can also be used to prepare various other organic compounds. These compounds have a wide range of application values in the fields of medicine, pesticides, dyes, fragrances, and more. Through different chemical reactions and synthetic pathways, various organic compounds with specific structures and functions can be transformed to meet the needs of different industries.
Research in the field of biomedical sciences
As a biomarker: Studies have shown that its derivatives can be used as biomarkers to monitor its residues and metabolism in organisms. For example, by using the acid hydrolyzable side chain of 4-hydroxybenzoyl hydrazine bound to tissues such as the liver as a marker, its residue in chickens can be monitored. This feature provides new means and methods for drug metabolism research and biological monitoring.
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.
FAQ
What is another name for 4-hydroxybenzoic acid?
It also known as p-hydroxybenzoic acid (PHBA), is a monohydroxybenzoic acid, a phenolic derivative of benzoic acid.
What is hydroxybenzoic acid?
Hydroxybenzoic acid refers to a type of aromatic carboxylic acid characterized by a hydroxyl group attached to a benzoic acid structure.
What is the solubility of 4-hydroxybenzoic acid?
4-Hydroxybenzoic acid is soluble in organic solvents such as DMSO and dimethyl formamide (DMF). The solubility of 4-hydroxybenzoic acid in these solvents is approximately 5 mg/ml. 4-Hydroxybenzoic acid is sparingly soluble in aqueous buffers.
What are the hazards of 4-hydroxybenzoic acid?
4-Hydroxybenzoic acid (CAS 99-96-7) is primarily hazardous due to its potential to cause serious eye damage, skin irritation, and respiratory irritation. It is harmful if swallowed and can cause toxic effects, including metabolic acidosis in extreme cases. While relatively low in acute toxicity, it exhibits weak estrogenic activity.
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