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Acethydrazide(Acetylhydrazine), also known as acetyl hydrazide or ethanoyl hydrazide, is an organic compound with the chemical formula C2H5N3O. It is a white crystalline solid that is soluble in water and various organic solvents. This compound belongs to the hydrazide family, characterized by the presence of the hydrazide functional group (-CONHNH2). Which is primarily used as a chemical intermediate in the synthesis of various pharmaceuticals and dyes.
Its reactive hydrazide group allows for versatile transformations, making it a key precursor in the preparation of heterocyclic compounds, particularly those containing nitrogen atoms. Additionally, it finds application in the production of pesticides and other agrochemicals due to its ability to modify the biological activity of molecules.
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Chemical Formula |
C2H6N2O |
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Exact Mass |
74.05 |
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Molecular Weight |
74.08 |
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m/z |
74.05 (100.0%), 75.05 (2.2%) |
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Elemental Analysis |
C, 32.43; H, 8.16; N, 37.81; O, 21.60 |
In the laboratory, it serves as a model compound for studying hydrazide chemistry, including its reactions with aldehydes, ketones, and acids. These reactions often lead to the formation of condensation products with potential use in material science and polymer chemistry.
Moreover, it has been investigated for its potential biological activities, such as antioxidant and antimicrobial properties, although further research is needed to fully explore its pharmacological potential. Safety measures should be taken when handling this compound due to its potential toxicity and reactivity.
Acethydrazide is an important chemical raw material, which can be used to synthesize analgesics, anticancer drugs, tooth corrosion inhibitors, platelet activity index inhibitors, antifogging agents for color fixers, stabilizers, metal pickling preservatives, etc. In particular, the use of acetylhydrazine as a raw material to prepare carbamate insecticides can avoid the toxicity to the human body and the environment caused by the direct use of methyl isocyanate.
Pharmaceutical Applications
Analgesics
Acetylhydrazine can be used in the synthesis of pain-relieving medications. These analgesics help alleviate pain by targeting specific receptors in the body.
Anticancer Drugs
The role of acetylhydrazine in the production of anticancer drugs is significant because it contributes to the development of new and effective treatments for cancer. Cancer is a complex and heterogeneous disease, and the ability to target and destroy cancer cells selectively is crucial for improving patient outcomes. By serving as an intermediate in the synthesis of anticancer drugs, acetylhydrazine helps to facilitate the development of these targeted therapies.
Intermediate in Drug Production
Acetylhydrazine serves as an important intermediate in the synthesis of certain anticancer drugs. This means that it is a crucial chemical compound used in the production process of these drugs.
Selective Cancer Cell Killing
Anticancer drugs synthesized using acetylhydrazine are often designed to selectively target cancer cells. This selectivity is crucial because it allows the drugs to destroy cancer cells while sparing healthy cells, thereby minimizing side effects.
Broad Spectrum of Activity
Acetylhydrazine-derived anticancer drugs can have a broad spectrum of activity, meaning they can be effective against multiple types of cancer. This makes them valuable tools in the oncologist's arsenal for treating a wide range of malignancies.
Potential for Reduced Neurotoxicity
Research suggests that certain derivatives of acetylhydrazine may have reduced neurotoxicity compared to other anticancer drugs. This is an important consideration, as neurotoxicity can be a significant side effect of many cancer treatments.
Dental Applications
By inhibiting the corrosion of teeth, acetylhydrazine-derived compounds help protect dental health. They can form protective layers on tooth enamel, shielding it from acidic attacks that lead to decay.
Protective Mechanisms
Formation of Protective Layers
Acetylhydrazine-derived compounds can interact with tooth enamel to form protective layers. These layers act as barriers that prevent acids and other harmful substances from penetrating the enamel and causing damage.
Neutralization of Acids
Some acetylhydrazine-derived compounds may have the ability to neutralize acids. This can be particularly beneficial in the oral environment, where acids produced by bacteria can erode tooth enamel and lead to decay.
Antimicrobial Properties
In addition to their protective effects on tooth enamel, acetylhydrazine-derived compounds may also possess antimicrobial properties. This means they can help to reduce the number of harmful bacteria in the mouth.
Dental Health Benefits
Prevention of Cavities
By forming protective layers on tooth enamel and neutralizing acids, these compounds can help prevent the formation of cavities. This is particularly important for maintaining long-term dental health and avoiding the need for fillings or other restorative treatments.
Reduction in Sensitivity
Tooth enamel that is protected by acetylhydrazine-derived compounds may be less sensitive to temperature changes and other stimuli. This can improve the overall comfort and function of the teeth.
Support for Dental Treatments
These compounds may also be useful as adjunctive treatments for existing dental problems. For example, they could be applied to teeth that have already undergone restorative treatments, such as fillings or crowns, to provide additional protection and reduce the risk of recurrent decay.
Hematological Applications
Acetylhydrazine's ability to regulate platelet activity is indeed a significant aspect of its potential physiological effects. Platelets are essential components of the blood clotting process, playing a crucial role in maintaining normal hemostasis (the prevention of excessive bleeding) and preventing thrombosis (the formation of blood clots within the blood vessels).
Regulation of Platelet Activity
Inhibition of Platelet Aggregation
Acethydrazide has been shown to have antiplatelet aggregatory effects, meaning it can inhibit the clustering of platelets that occurs in response to vascular injury. This is important because excessive platelet aggregation can lead to the formation of occlusive blood clots, which can obstruct blood flow and cause tissue ischemia (lack of oxygen and nutrients due to inadequate blood supply).
Modulation of Platelet Function
In addition to inhibiting aggregation, acetylhydrazine may also affect other aspects of platelet function, such as adhesion (the attachment of platelets to the injured vessel wall) and secretion (the release of granular contents by platelets). By modulating these functions, acetylhydrazine can help maintain a balanced platelet response to vascular injury.
Implications for Hemostasis and Thrombosis
Maintenance of Normal Hemostasis
By inhibiting excessive platelet aggregation and modulating platelet function, acetylhydrazine can help maintain normal hemostasis. This is crucial for preventing bleeding after vascular injury and ensuring that blood clots form appropriately to seal the wound.
Prevention of Thrombosis
On the other hand, acetylhydrazine's antiplatelet aggregatory effects can also help prevent thrombosis. By reducing the tendency of platelets to cluster and form occlusive clots, the compound can lower the risk of cardiovascular events such as heart attacks and strokes.
Potential Clinical Applications
The ability of acetylhydrazine to regulate platelet activity makes it a potential candidate for the treatment of various cardiovascular and hematological disorders:
Antiplatelet Therapy
Acetylhydrazine could be developed as an antiplatelet agent for use in patients at risk of thrombosis. Its antiplatelet aggregatory effects may make it a useful adjunct to conventional antiplatelet therapies such as aspirin or clopidogrel.
Management of Bleeding Disorders
In patients with bleeding disorders, acetylhydrazine's ability to maintain normal hemostasis may be beneficial. However, its use in this context would need to be carefully monitored to ensure that it does not exacerbate bleeding tendencies.
Manufacturing process
The production of acethydrazide is mainly achieved through chemical synthesis. The core reaction is the condensation reaction between acetic acid ester and hydrazine hydrate. The specific process is as follows:
Raw material preparation
Ethyl acetate (CH₃COOC₂H₅): As the acetyl donor, it should have a purity of ≥ 98%.
Hydrazine hydrate (NH₂NH₂·H₂O): Provides the hydrazine group, with a concentration usually ranging from 80% to 100%.
Catalyst (optional): Such as activated alumina (Al₂O₃), which can accelerate the reaction and increase the yield.
Reaction conditions
Temperature: Heating and reflux (approximately 70-80℃), for several hours to ensure complete reaction.
Pressure: Atmospheric pressure or slightly positive pressure (such as 18 mmHg), to control the boiling point and reduce by-products.
Molar ratio: The molar ratio of ethyl acetate to hydrazine hydrate is usually 1:1. Excess hydrazine can increase the yield.
Reaction equation:CH3COOC2H5+NH2NH2⋅H2O→CH3CONHNH2+C2H5OH
Post-treatment steps
Decompression distillation: Remove unreacted raw materials and solvents (such as ethanol), and recover the crude acetylhydrazine.
Re-crystallization: Recrystallize using ethanol or a water-ethanol mixed solvent to increase purity to ≥ 98%.
Drying: Store in a cool and dry place in an airtight container to prevent moisture absorption and caking.
Quality control
Purity testing
High Performance Liquid Chromatography (HPLC): Quantitative analysis of acetylhydrazine content, ensuring ≥98%.
Gas Chromatography (GC): Detection of volatile impurities, such as unreacted ethyl acetate or hydrazine derivatives.
Physical indicators verification
Melting point determination: Confirm that the melting point range is within 58-68℃, and deviations exceeding ±2℃ require re-purification.
Water content determination: Using Karl Fischer method to detect water content, typically ≤0.5%.
Safety and environmental protection
Wastewater treatment: The reaction wastewater contains hydrazine substances, which need to be neutralized and then undergo biochemical treatment to avoid environmental pollution.
Emission control: The reaction vessel needs to be equipped with a condensation reflux device to reduce the emission of volatile organic compounds (VOCs).
I. First Synthesis and Structural Establishment
The discovery of acetylhydrazine is closely linked to the systematic research on hydrazide compounds in the late 19th century. In 1895, the German chemist Theodor Curtius, during his investigations into the reactions between hydrazine and carboxylic acid derivatives, successfully prepared acetylhydrazine for the first time via the hydrazinolysis of ethyl acetate with hydrazine hydrate, and preliminarily reported its fundamental physicochemical properties. He identified the molecular composition and structural characteristics of the compound, confirming it as the hydrazide derivative of acetic acid, laying an important foundation for subsequent studies on analogous compounds.
II. Early Research and Property Refinement
In the early 20th century, researchers carried out more detailed studies on the physicochemical properties of acetylhydrazine, accurately determining its melting point, solubility, and reactivity. It was confirmed to possess the dual reactive characteristics of both acyl and hydrazino groups. Work in this period further verified the reliability of Curtius' synthetic route and completed the basic data set for the compound, allowing it to evolve from a newly identified laboratory substance into a stably usable intermediate in organic synthesis.
III. Industrialization and Recognition of Application Value
With the development of heterocyclic chemistry and medicinal chemistry, the application potential of acetylhydrazine has been continuously explored. After the mid-20th century, extensive research emerged on its use as a starting material for the synthesis of pharmaceutical and agrochemical intermediates, driving its transition from laboratory-scale preparation to industrial-scale production. Its discovery history has become a typical example of translation from basic organic chemistry research to industrial application, and it still plays an important role in the field of fine chemicals today.
FAQ
What is the structure of acetyl hydrazide?
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Acetyl Hydrazide, with a structural formula of C2H6N2O, is a high purity powder with a purity level of over 98.0%. This product is commonly used in pharmaceutical applications. It is stored at room temperature and has a CAS No of 1068-57-1.
What is the CAS number of acetyl hydrazine?
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1068-57-1 CAS | ACETHYDRAZIDE | Hydrazides | Article No. 00527.
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