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4-Acetoxyindole is an organic compound widely used in the fields of medicine and chemistry. Its molecular formula is C10H9NO2. It is a white to light yellow crystalline powder with a weak acidic smell. The solubility is relatively low, only about 1-2g of this organic compound can be dissolved in 100ml of water. The solubility in polar solvents such as ethyl acetate, ethanol, and dimethylformamide is relatively high. The compound is susceptible to moisture and oxidation, so certain precautions are required during storage and use. Since the substance is an organic compound, it does not have a definite boiling point. Instead, when the substance is heated to high temperatures, it tends to break down and release toxic gases. is an organic molecule, so it has a weak electrical conductivity. But under some special conditions, the substance can still exhibit some electrical properties. For example, in some organic solvents, the conductivity can be measured by a conductivity meter. In addition, the substance also has a certain optical activity, which will rotate the incident light. It is an organic compound with a wide range of applications. Through continuous development and application, various applications will continue to bring many important influences and contributions to medicine, chemistry, agriculture and life.
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C.F |
C10H9NO2 |
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E.M |
175 |
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M.W |
175 |
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m/z |
175 (100.0%), 176 (10.8%) |
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E.A |
C, 68.56; H, 5.18; N, 8.00; O, 18.27 |
4-acetoxyindole, as an important organic compound, has a wide range of applications in the field of dyes. Its unique chemical structure and properties make it one of the key raw materials for synthesizing various color dyes.
Basic properties
It is an organic intermediate that can exist stably at room temperature and pressure, often appearing as a gray white to beige powder. It is soluble in dichloromethane, chloroform DMSO, Organic solvents such as ethanol and methanol. This compound belongs to irritant substances and can be synthesized through specific chemical reaction conditions.
Application in the textile industry
Improve the quality of textiles
The application in the textile industry can significantly improve the quality of textiles. By using these dyes, textiles with bright colors and high color fastness can be obtained. These textiles not only have a good appearance effect, but also are not easily faded or discolored during use, thereby extending the service life of the textiles.
Meet diverse market demands
With the continuous improvement of consumers' requirements for textile color and quality, the market's demand for dyes is becoming increasingly diversified. As a dye with excellent performance, it can meet the market's demand for textiles of different colors and purposes.
For example, in the clothing industry, it is possible to obtain clothing products with bright colors and rich patterns by using it. These products not only meet consumers' demand for aesthetics, but also are not easily faded or deformed during use, improving the comfort and durability of clothing.
Promote the development of the textile industry
Applications can also promote the development of the textile industry. By using these dyes, more innovative and competitive textile products can be developed. These products not only enhance the added value and market competitiveness of textiles, but also promote the transformation, upgrading, and sustainable development of the textile industry.
Application in the printing industry
Improve the color effect of printed materials
The application in the printing industry can significantly improve the color effect of printed materials. By using these dyes, printed materials with bright colors and clear patterns can be obtained. These printed materials not only have good visual effects, but also are not easily faded or discolored during use, thereby improving the quality and durability of the printed materials.
Meet personalized market demands
With the continuous increase in consumer demand for personalized printed materials, the market's demand for dyes is also becoming increasingly diversified. As a dye with excellent performance, it can meet the market's demand for personalized printed products.
For example, in the packaging printing industry, packaging products with bright colors and unique patterns can be obtained by using dyes. These products not only enhance their added value and market competitiveness, but also meet consumers' demand for personalized packaging.
Promote the advancement of printing technology
Applications can also drive advances in printing technology. By using these dyes, more innovative and competitive printing technologies can be developed. These technologies not only improve the quality and efficiency of printed materials, but also promote the transformation, upgrading, and sustainable development of the printing industry.
Application in the dyeing industry
Improve dyeing efficiency
The application in the dyeing industry can significantly improve dyeing efficiency. By using these dyes, dyeing time can be shortened, energy consumption and costs can be reduced. At the same time, these dyes also have good dispersibility and permeability, allowing dye molecules to be evenly distributed on fibers or substrates, thereby improving the uniformity and firmness of dyeing.
Meet environmental requirements
With the continuous improvement of environmental awareness, the demand for environmentally friendly dyes in the market is also increasing. As an environmentally friendly dye, dyes can meet the market's demand for eco-friendly dyes. These dyes do not produce harmful substances during use, are environmentally friendly, and easy to handle.
Promote innovation in dyeing technology
The application of 4-acetoxyindol dye can also promote innovation in dyeingtechnology. By using these dyes, more innovative and competitive dyeing technologies can be developed. These technologies not only improve the quality and efficiency of dyeing, but also promote the transformation, upgrading, and sustainable development of the dyeing industry.
synthesis methods
1. Hydrazide method:
It is one of the most commonly used methods for preparing 4-Acetoxyndole. The method utilizes the electrophilicity of indole to react with the nucleophilicity of acetic acid hydrazine to generate acetic acid hydrazide compound. Subsequently, the compound undergoes a condensation reaction under acidic conditions to generate 4-Acetoxyindole.
2. Iodination method:
It is another method for preparing 4-Acetoxyndole. The reaction principle of the method is to use iodine to remove unstable methyl carboxylic acid groups to form the structural skeleton of 4-Acetoxyndole.
3. Oxidation method:
4-Acetoxyndole is prepared by using 2,3-dioxane-1,4-diketone (DDQ) as an oxidizing agent. In this reaction, indole, the precursor of 4-Acetoxyndole, is oxidized first to form indole, and then to 2,3-dioxindole intermediate, and finally to 4-Acetoxyndole product.
4. Suzuki reaction:
It is one of the most commonly used palladium-catalyzed coupling reactions in modern organic synthesis, and this method is also used to prepare 4-Acetoxyndole. The steps of the method are firstly to carry out coupling reaction of 2-bromoindole and phenylboronic acid under the presence of palladium catalyst and basic condition to form N-phenylindole. Then N-phenylindole and acetic anhydride are subjected to acetic acidification in the presence of sodium hydroxide to finally obtain 4-Acetoxyindol.
4-Acetoxyindole is an organic compound belonging to the class of indole derivatives, characterized by the presence of an acetoxy group (-OCOCH₃) attached to the fourth position of the indole ring system. This specific substitution pattern imparts unique chemical and biological properties, distinguishing it from other indole derivatives.
Structurally, indole itself is a bicyclic compound consisting of a benzene ring fused to a pyrrole ring. The introduction of the acetoxy group at the 4-position modifies the electronic and steric environment of the indole, influencing its reactivity and interactions with other molecules. This substitution can affect the compound's solubility, stability, and biological activity.
Chemically, it can participate in various reactions typical of indoles, such as electrophilic aromatic substitution and nucleophilic attack, particularly at positions that are activated or deactivated by the acetoxy group. The presence of the ester functionality also allows for hydrolysis under acidic or basic conditions, potentially leading to the formation of 4-hydroxyindole and acetic acid.
Biologically, indole derivatives are of significant interest due to their presence in natural products and their potential pharmacological activities. Some indole derivatives are known to exhibit antimicrobial, anti-inflammatory, or neuroactive properties. The acetoxy group may modulate these activities by altering the compound's ability to interact with biological targets, such as receptors or enzymes.
In research settings, it may serve as a synthetic intermediate for the preparation of more complex indole-based compounds, including those with therapeutic potential. Its synthesis typically involves the acylation of 4-hydroxyindole under appropriate conditions to introduce the acetoxy group selectively.
Overall, 4-acetoxyindole represents an important compound in organic and medicinal chemistry, offering insights into the structure-activity relationships of indole derivatives and serving as a building block for the development of novel chemical entities with diverse applications.
The molecular formula of 4-Acetoxyindole is C₁₀H₉NO₂, with a molecular weight of 175.18 g/mol. Its core structure consists of an indole ring and an acetoxy group (-OCOCH₃). This compound appears as a grayish-white to beige solid at room temperature and pressure. Its melting point is 100-102℃, the predicted boiling point is 339.1±15.0℃, the density is approximately 1.255 g/cm³ (25℃), and the refractive index is 1.633. Its solubility is selective and it is slightly soluble in organic solvents such as chloroform, DMSO, and methanol, but has extremely low solubility in water. Storage conditions require strict avoidance of light and sealing for storage in a cool, dry environment at 2-8℃ to prevent decomposition or deterioration.
In terms of chemical properties, the acetoxy group (-OCOCH₃) of 4-Acetoxyindole exhibits the typical reactivity of ester compounds. For instance, under acidic or alkaline conditions, the acetoxy group readily undergoes hydrolysis reactions, generating 4-Hydroxyindole and acetic acid. This characteristic is crucial in the design of synthetic pathways, such as through the acylation reaction of 4-Hydroxyindole with acetic anhydride, which can efficiently produce 4-Acetoxyindole: Dissolve 4-Hydroxyindole in dichloromethane (DCM), dropwise add pyridine and acetic anhydride at 0-5℃, warm the reaction mixture to 20-25℃ and stir for 3 hours. After post-treatment (such as washing with water, washing with saturated sodium bicarbonate solution, drying and concentration), the target product can be obtained, with a purity of over 99%.
Although the toxicity data of 4-Acetoxyindole is not fully clear, existing studies suggest that it may cause irritation to the skin, eyes and respiratory tract. For example, inhaling dust may cause respiratory discomfort, skin contact requires washing with soap and plenty of water, and eye contact requires immediate rinsing with water as a precautionary measure. According to the GHS classification, this compound is labeled as "Xi" (irritant substance) and is accompanied by hazard descriptions (such as H302, H315, H319, H332, H335) and precautionary instructions (such as P280, P305+P351+P338, P310). Therefore, during the operation, protective equipment (such as gloves, goggles and dust masks) should be worn, and the operation should be carried out in a well-ventilated environment.
From the perspective of application fields, 4-Acetoxyindole is mainly used as a pharmaceutical intermediate and an organic synthesis raw material. For instance, it is a key precursor for synthesizing indole derivatives, which are of great value in drug research, such as anti-tumor, anti-inflammatory or antibacterial active molecules. Moreover, 4-Acetoxyindole can also be applied in the field of materials science, for example, for the preparation of functional polymers or fluorescent probes. In industrial production, the synthesis process of 4-Acetoxyindole needs to take into account both cost and efficiency. For instance, by optimizing reaction conditions (such as temperature, solvent and catalyst dosage), the yield can be significantly increased while reducing the generation of by-products.
In terms of market supply, the purity specifications of 4-Acetoxyindole are diverse, ranging from reagent grade (98%-99%) to industrial grade (≥95%). The prices vary depending on purity and packaging specifications. For instance, the price of 5 grams of reagent grade product is approximately 49 yuan, while the price of 25 kilograms of industrial grade product may be as low as 1 US dollar per kilogram. Major suppliers include Sigma Aldrich, Aladdin, Shaoyuan Technology and other domestic and foreign enterprises. Their products are widely used in the fields of research, pharmaceuticals and chemicals.
Frequently Asked Questions
Why is its "4-acetoxyl" structure an ideal "protective and guiding" group for the synthesis of key intermediates such as pregabalin?
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The strong electron withdrawing effect of acetoxy group can significantly activate the 3rd position of indole, facilitating the introduction of the desired side chain. After completion of the construction, the acetoxy group can be easily converted into the 4-hydroxyindole structural unit required for drug synthesis through mild alkaline hydrolysis.
How is it enzymatically hydrolyzed in living organisms and may mimic or interfere with the metabolism of indoleamine neurotransmitters?
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Its acetyl group can be hydrolyzed by non-specific esterases to generate 4-hydroxyindole in situ. The latter is a potential intermediate or regulator of the metabolic network of indoleamine substances such as serotonin in the body, which may affect the levels of related neurotransmitters, but the specific mechanism is unclear.
What is the potential value of its "indole acetoxy" combination in the field of organic luminescent materials?
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Indole is a classic electron donor group that may form an intramolecular push-pull electron system when combined with electron withdrawing acetoxy groups. This structural modification can adjust the fluorescence emission wavelength and efficiency of compounds, making it a candidate structure for designing novel organic luminescent molecules.
What are the advantages of its acetylated form in terms of chemical stability and reactivity compared to simple 4-hydroxyindole?
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Acetylation protects the hydroxyl group, making it more stable against air oxidation and easier to store and handle. Meanwhile, it alters the electron cloud distribution of the indole ring, potentially endowing it with unique electrophilic/nucleophilic reactivity distinct from free hydroxyindole, expanding its synthetic applications.
In natural product chemistry, is it used as a hypothetical precursor or synthetic equivalent for certain alkaloids?
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There is a hypothesis that certain natural alkaloids containing 4-hydroxy or 4-methoxyindole structures (such as certain β - Capolin derivatives) may undergo alkylation or cyclization via 4-acetoxyindole as an active intermediate in their biogenic synthesis, but there is no conclusive evidence yet.
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