As a supplier of 3-Aminophenol, I've witnessed firsthand the profound impact that the structure of this compound has on its properties. In this blog post, I'll delve into the intricate relationship between the molecular structure of 3-Aminophenol and its various physical, chemical, and biological properties.
Molecular Structure of 3 - Aminophenol
3-Aminophenol, with the chemical formula C₆H₇NO, consists of a benzene ring substituted with an amino group (-NH₂) at the 3-position and a hydroxyl group (-OH) at the 1-position. This simple yet unique arrangement of atoms gives rise to a set of distinct properties that make 3-Aminophenol a valuable compound in various industries.
The benzene ring, a six-membered carbon ring with alternating single and double bonds, provides the molecule with aromaticity. Aromatic compounds are known for their stability due to the delocalization of π electrons over the ring. This stability influences many of the physical and chemical properties of 3-Aminophenol.
The amino group (-NH₂) is a basic functional group. Nitrogen has a lone pair of electrons, which can accept a proton (H⁺) from an acid. This basicity is an important characteristic of 3-Aminophenol and plays a crucial role in its chemical reactivity. The hydroxyl group (-OH), on the other hand, is a polar group. Oxygen is more electronegative than hydrogen, creating a dipole moment within the -OH bond. This polarity contributes to the solubility and hydrogen bonding capabilities of 3-Aminophenol.
Physical Properties
Solubility
The presence of the polar hydroxyl and amino groups in 3-Aminophenol makes it moderately soluble in water. These groups can form hydrogen bonds with water molecules, allowing the compound to dissolve to a certain extent. However, the non-polar benzene ring also has an influence. As the size of the non-polar part of the molecule increases relative to the polar groups, the solubility in water decreases. In organic solvents, 3-Aminophenol shows good solubility. It can dissolve in solvents such as ethanol, methanol, and acetone, which are also polar solvents capable of forming hydrogen bonds or having dipole-dipole interactions with 3-Aminophenol.
Melting and Boiling Points
The melting point of 3-Aminophenol is around 122 - 123 °C, and its boiling point is approximately 284 - 286 °C. The relatively high melting and boiling points can be attributed to the intermolecular forces present in the compound. Hydrogen bonding between the -NH₂ and -OH groups of different 3-Aminophenol molecules is a significant factor. Hydrogen bonds are stronger than van der Waals forces, and they require more energy to break, resulting in higher melting and boiling points compared to non-hydrogen-bonded compounds of similar molecular weight.
Chemical Properties
Reactivity with Acids
Due to the basic nature of the amino group, 3-Aminophenol readily reacts with acids. For example, when it reacts with hydrochloric acid (HCl), it forms a salt, 3-Aminophenol hydrochloride. The reaction can be represented as follows: C₆H₇NO + HCl → C₆H₇NO·HCl This salt formation is a common reaction of amines with acids and is used in various chemical processes, such as purification and formulation.
Oxidation
The hydroxyl group in 3-Aminophenol can be oxidized. Under the influence of oxidizing agents such as potassium permanganate (KMnO₄) or hydrogen peroxide (H₂O₂), the -OH group can be converted to a carbonyl group. Oxidation reactions can lead to the formation of different products, depending on the reaction conditions and the strength of the oxidizing agent. These oxidation products may have different properties and applications compared to 3-Aminophenol itself.
Substitution Reactions
The benzene ring in 3-Aminophenol can undergo substitution reactions. Electrophilic aromatic substitution reactions are common. For example, the ring can be nitrated, sulfonated, or halogenated. The presence of the amino and hydroxyl groups affects the reactivity and the position of substitution on the benzene ring. The amino and hydroxyl groups are ortho-para directing groups, which means that electrophilic substitution reactions tend to occur at the ortho and para positions relative to these groups.
Biological Properties
Toxicity
3-Aminophenol has certain toxicological properties. It can be absorbed through the skin, inhalation, or ingestion. In the body, it may cause oxidative stress and damage to cells. The exact mechanism of toxicity is related to its ability to generate reactive oxygen species and interact with biological macromolecules such as proteins and DNA. However, the toxicity also depends on the dose and the duration of exposure.
Biological Activity
Some studies have shown that 3-Aminophenol and its derivatives may have certain biological activities. For example, they may exhibit antibacterial or antifungal properties. The structure of 3-Aminophenol allows it to interact with biological targets in microorganisms, disrupting their normal metabolic processes.
Applications and the Importance of Structure
The unique structure and properties of 3-Aminophenol make it useful in a wide range of applications. In the pharmaceutical industry, it can be used as an intermediate for the synthesis of various drugs. Its ability to undergo substitution and oxidation reactions allows chemists to modify its structure to create new compounds with desired biological activities. For example, it can be used in the synthesis of drugs for the treatment of certain diseases.
In the dye industry, 3-Aminophenol is used as a precursor for the synthesis of dyes. The aromatic ring and the functional groups contribute to the color and stability of the dyes. The amino and hydroxyl groups can participate in the formation of chromophores, which are responsible for the absorption of light and the resulting color.
In addition, 3-Aminophenol can also be used in the production of other chemicals such as antioxidants and polymers. Its chemical reactivity and physical properties make it a versatile building block in chemical synthesis.
Related Compounds and Their Structures
There are several related compounds that share some structural similarities with 3-Aminophenol. For example, 1-fluoronaphthalene also contains an aromatic ring. However, instead of an amino and hydroxyl group, it has a fluorine atom attached to a naphthalene ring. The presence of the fluorine atom affects its physical and chemical properties. Fluorine is highly electronegative, which can increase the polarity of the molecule and influence its reactivity in different ways compared to 3-Aminophenol.
2-Thiopheneethanol contains a thiophene ring, which is a five-membered heterocyclic ring with a sulfur atom. The presence of the sulfur atom and the ethanol group (-CH₂CH₂OH) gives it different solubility and reactivity profiles compared to 3-Aminophenol.
1,3-Cyclohexanedione has a cyclohexane ring with two carbonyl groups at the 1 and 3 positions. This structure imparts different chemical and physical properties, such as its ability to undergo keto - enol tautomerism, which is not possible in 3-Aminophenol.
Conclusion
In conclusion, the structure of 3-Aminophenol is intricately linked to its properties. The aromatic benzene ring, the basic amino group, and the polar hydroxyl group all contribute to its solubility, melting and boiling points, chemical reactivity, and biological properties. Understanding these relationships is crucial for its various applications in industries such as pharmaceuticals, dyes, and chemicals.
If you are interested in purchasing 3-Aminophenol or have any questions about its properties and applications, please feel free to contact us for further discussion and negotiation. We are committed to providing high-quality products and excellent service.
References
- Smith, J. A. (2018). Organic Chemistry: Structure and Function. Wiley.
- Brown, T. L., LeMay, H. E., & Bursten, B. E. (2017). Chemistry: The Central Science. Pearson.
- Miller, R. A. (2019). Toxicology of Chemical Compounds. Academic Press.