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What are the chemical properties of 4-amino-3-iodobenzonitrile?
4-Hydroxy-3-nitrophenylacetamide is an organic compound with unique chemical properties that are critical to the fields of organic synthesis and medicinal chemistry. The following are some of its chemical properties:
1. ** Acid and alkaline **: This compound contains hydroxyl groups. Due to the high electronegativity of oxygen atoms, hydroxyl hydrogen has a certain acidity, and can lose protons in a strong alkali environment to form corresponding salts. However, its acidity is relatively weak, and its dissociation constant is small compared with typical inorganic acids. At the same time, the nitrogen atom in the molecular lactam group has unshared electron pairs, which is theoretically alkaline. However, due to the electron-absorbing conjugation effect of the carbonyl group in the amide group, the electron cloud density on the nitrogen atom decreases, and the alkalinity is not significant. It is usually difficult to form a stable salt with acids like amines.
2. ** Substitution Reaction **: The benzene ring is affected by the localization effect of nitro and hydroxyl groups. Nitro is a strong electron-absorbing group, which reduces the electron cloud density of the benzene ring and makes the electron cloud density of the benzene ring an intergenus localization group; hydroxyl is the power supply group and is the ortho and para-localization group. Under the combined action of the two, the electrophilic substitution reaction activity on the benzene ring changes, which mainly occurs in the ortho and para For example, when a halogenation reaction occurs, electrophilic reagents such as bromine are more likely to attack the ortho and para-position of hydroxyl groups to generate corresponding halogenated products.
3. ** Redox Reaction **: The nitro group in the molecule can be reduced. Under the action of suitable reducing agents such as iron, hydrochloric acid, lithium aluminum hydride, etc., the nitro group is gradually reduced, and the first group is formed into nitroso group, and the amino group can be obtained by continuous reduction. The hydroxyl group may be oxidized to carbonyl or carboxyl group under the action of appropriate oxidizing agents such as potassium permanganate. The specific product depends on the reaction conditions, such as reaction temperature, oxidant dosage, and pH of the reaction system.
4. ** Hydrolysis Reaction **: Amide bonds can be hydroly Under acidic conditions, hydrolysis generates 4-hydroxy-3-nitrobenzoic acid and ammonium salts; under alkaline conditions, hydrolysis generates 4-hydroxy-3-nitrobenzoate and ammonia. The hydrolysis reaction rate is related to factors such as temperature and acid-base concentration. Heating up and increasing acid-base concentration usually accelerate the hydrolysis reaction rate.
What are the physical properties of 4-amino-3-iodobenzonitrile?
4-Hydroxy-3-nitrophenylacetamide is one of the organic compounds. Its physical properties are as follows:
Looking at its color state, at room temperature, it is mostly white to light yellow crystalline powder. The characteristics of this color state can be directly identified by the naked eye. In various experiments and production scenarios, it is a key characteristic for preliminary identification.
In terms of its melting point, it is about 198-202 ° C. The melting point is the critical temperature at which a substance changes from solid to liquid. This property plays a huge role in the purity identification, separation and purification of compounds. By measuring the melting point, the purity of the substance can be determined. If the measured melting point is in good agreement with the theoretical value, the purity is good; otherwise, it may contain impurities.
As for solubility, 4-hydroxy-3-nitrophenylacetamide is slightly soluble in water. Water is a common solvent, and the difference in solubility has a far-reaching impact on the separation of substances and the choice of reaction media. The characteristics of micro-solubility in water mean that in the water system, its degree of dispersion is limited, which also determines that it needs special consideration in the relevant aqueous phase reaction or operation. However, it is soluble in some organic solvents, such as ethanol, dichloromethane, etc. Organic solvents have their own characteristics, with moderate polarity of ethanol and good lipid solubility of dichloromethane, indicating that the compound has certain lipophilicity and is used in the fields of organic synthesis and extraction. This solubility characteristic provides a basis for selecting an appropriate solvent, so that the reaction or operation can be carried out more effectively.
What are the main uses of 4-amino-3-iodobenzonitrile?
4-Amino-3-pyridinecarboxylic acid is an important organic compound that has key uses in many fields.
In the field of medicinal chemistry, it can be regarded as a key intermediate in drug synthesis. Due to its specific chemical structure and activity, it can construct complex molecules with specific pharmacological activities through a series of chemical reactions. For example, some drugs used to treat cardiovascular diseases are synthesized with 4-amino-3-pyridinecarboxylic acid as the starting material. By modifying and transforming its amino and carboxyl functional groups, drug molecules that fit specific targets and have good efficacy and low side effects can be prepared.
In the field of materials science, this compound has also emerged. It can participate in the preparation of functional polymer materials. By virtue of its own reactivity, polymerization with other monomers occurs, resulting in polymer materials that may have unique electrical, optical or mechanical properties. For example, in the preparation of some optoelectronic materials, the introduction of 4-amino-3-pyridinecarboxylic acid structural units can optimize the charge transport properties and luminous efficiency of materials, thus providing impetus for the development of new display technologies and optoelectronic devices.
In the field of organic synthetic chemistry, 4-amino-3-pyridinecarboxylic acid is an extremely important building block. Organic chemists can use various organic reactions, such as esterification and amidation, to construct a diverse library of organic compounds according to their structural characteristics, providing rich materials and bases for the creation of new substances and the study of organic synthesis methodologies. In short, 4-amino-3-pyridinecarboxylic acid plays an irreplaceable role in many scientific and technological fields due to its unique structure and reactivity.
What are the synthesis methods of 4-amino-3-iodobenzonitrile?
There are many ways to synthesize 4-hydroxy-3-nitrophenylacetamide. The following are common methods:
First, p-hydroxy acetophenone is used as the starting material. First, p-hydroxy acetophenone is nitrified with nitric acid under suitable conditions. Nitric acid is used as the nitrifying agent, and sulfuric acid is often used as the catalyst and reaction medium. This step results in 4-hydroxy-3-nitroacetophenone. Then, the amidation reaction of 4-hydroxy-3-nitroacetophenone is carried out. Ammonia or amine compounds can be used, and the conversion to 4-hydroxy-3-nitrophenylacetamide can be achieved under the conditions of heating or adding a condensing agent such as DCC (dicyclohexyl carbodiimide) in an appropriate solvent. The reaction principle is that the nitration reaction introduces nitro groups into the phenyl ring at specific positions, changing the electron cloud density of the phenyl ring, and the amidation reaction is the condensation of carbonyl groups with amino groups to form amide bonds.
Second, starting from p-aminophenol. First, p-aminophenol is acetylated. Acetyl chloride or acetic anhydride is often used as an acetylation reagent. Under the catalysis of bases, such as pyridine, p-acetaminophenol is formed. This step aims to protect the amino group and avoid the overreaction of the amino group in the subsequent reaction. Then carry out the nitration reaction, and select a suitable nitration system to introduce nitro groups into the phenyl ring to obtain 4-acetamino-3-nitrophenol. Finally, through hydrolysis, under acidic or basic conditions, the acetyl group is removed, and the amino group is restored, and an amide bond is formed with the carbonyl group on the phenyl ring to achieve the synthesis of 4-hydroxy-3-nitrophenylacetamide. This route uses group protection and de-protection strategies to skillfully control the reaction check point and process.
Third, m-nitrophenol is used as the raw material. First, m-nitrophenol and halogenated acetate undergo a nucleophilic substitution reaction under basic conditions, such as the presence of bases such as sodium hydroxide or potassium carbonate. The halogen atom of the halogenated acetate is replaced by a phenoxy negative ion to form 3-nitrophenoxy acetate. Subsequently, the ester group is hydrolyzed and converted into 3-nitrophenoxy acetic acid under the catalysis of acid or base. Finally, the target product 4-hydroxy-3-nitrophenylacetamide is synthesized through an amidation reaction with ammonia or amine. This pathway takes advantage of the nucleophilicity of phenolic compounds and constructs the target molecular structure through multi-step reactions.
What are the precautions for 4-amino-3-iodobenzonitrile in storage and transportation?
In the storage and transportation of ethyl 4-hydroxy-3-iodobenzoate, the following things must be paid attention to:
First, the control of temperature and humidity. The properties of this compound may be affected by the change of temperature and humidity. Storage should be selected in a cool and dry place, away from high temperature and humidity. High temperature can cause it to accelerate the reaction and decomposition, and humid environment may cause adverse reactions such as hydrolysis, which will damage its purity and quality. For example, "Tiangong Kaiwu" said: "Everything has its own characteristics, and it will be stored if it follows its own characteristics, and it will die if it follows its own characteristics." Materials have their own inherent characteristics, and the temperature and humidity are appropriate to ensure the stability of the substance.
Second, protection from light. Ethyl 4-hydroxy-3-iodobenzoate or photosensitive, under light or induced luminescent chemical reaction, resulting in structural changes and quality degradation. When transporting and storing, it is advisable to use opaque packaging materials, such as dark bottles and cans or wrapped in shading paper, to prevent direct light.
Third, isolated storage. Do not mix and transport with oxidants, reducing agents, acids, bases and other substances. Because its chemical structure contains hydroxyl groups, iodine and other functional groups, it can react with the above substances. For example, "Tiangong Kaiqi" records the production of various materials, and different substances need to be classified and disposed of to prevent mutual interference. This compound should also be separated from those with different reactivity to ensure safety and stability.
Fourth, the packaging is sturdy. During transportation, prevent packaging damage caused by collision and vibration. The packaging needs to be selected with appropriate materials and strength to ensure that the compound is not damaged during loading, unloading and transportation. If the packaging is damaged, substances leak, or cause quality problems, and there are potential safety hazards.
Fifth, follow the regulations. Whether it is storage or transportation, it should be strictly operated in accordance with the relevant regulations and standards of chemicals. From packaging labels to transportation documents, compliance is required for supervision and traceability, to ensure the safety of personnel and the environment.
