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Mar. 25th 2025
3-Hydroxypiperidine(3-PIPERIDINOL) is a chemical compound belonging to the class of heterocyclic amines, specifically featuring a piperidine ring with a hydroxyl (-OH) group attached to the carbon atom at the 3-position. Its structure can be visualized as a six-membered ring containing five carbon atoms and one nitrogen atom, with an additional hydroxyl group bonded to one of the carbon atoms.
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| Chemical Formula | C5H11NO |
| Exact Mass | 101.08 |
| Molecular Weight | 101.15 |
| m/z | 101.08 (100.0%), 102.09 (5.4%) |
| Elemental Analysis | C, 59.37; H, 10.96; N, 13.85; O, 15.82 |
This compound exhibits unique physical and chemical properties, including its ability to form hydrogen bonds due to the presence of the hydroxyl group, which can influence its solubility and interactions with other molecules. It is a polar compound and is generally soluble in polar solvents such as water and alcohols.In the context of chemical synthesis, it serves as an important intermediate or building block for the preparation of various derivatives with diverse applications. These derivatives may find use in the pharmaceutical industry as active ingredients or key intermediates in drug synthesis, or in the development of materials science for the creation of polymers and other advanced materials.Furthermore, due to its specific structural features, it has been studied for its potential biological activities, including its ability to interact with biological receptors and enzymes. However, further research is required to fully understand its biological effects and explore its potential therapeutic uses.
In summary, the product is a versatile heterocyclic amine with a range of applications in chemical synthesis and potential biological significance, making it an area of interest for researchers in various scientific fields.
Applications in Fine Chemicals and Materials Industry
The fine chemicals and materials industry imposes stringent requirements on the purity, reactivity and structural compatibility of intermediates. Benefiting from its unique heterocyclic structure and difunctional characteristics, 3-Hydroxypiperidine has become an indispensable core raw material in this field. It is widely applied in multiple segmented sectors including fragrance synthesis, resin and coating modification, chiral material preparation, and functional additive development. It not only improves product performance but also expands application boundaries, driving the upgrading and sustainable development of the fine chemical and materials industries.
1.1 Applications in Fragrance Synthesis
In the fragrance industry, heterocyclic compounds serve as core components of high-end flavors and fragrances due to their distinctive aroma characteristics and long-lasting scent retention. As a nitrogen-containing heterocyclic intermediate, it is mainly utilized to synthesize lactone fragrances, oxygen-containing heterocyclic fragrances and nitrogen-containing heterocyclic fragrances. Its secondary alcohol and secondary amine groups can participate in acylation, alkylation, cyclization and other chemical reactions to construct aroma-specific molecular structures, while enhancing the stability and lasting performance of flavors. It is extensively used in food flavors, daily chemical fragrances, tobacco flavors and other fields.
In the field of food flavors, it reacts with carboxylic acids via esterification to produce lactone fragrances with milky, fruity or nutty notes. Such fragrances feature mild taste, pure aroma and non-irritating properties, and are commonly applied in the flavoring of dairy products, baked goods, beverages and other commodities. For instance, 3-hexanoyloxypiperidine, synthesized through the esterification of it and caproic acid, delivers a rich creamy fragrance and is deployed in the flavor formulation of cream cakes, ice cream, milk beverages and similar products.
An addition dosage of only 0.01%–0.1% can achieve optimal flavoring effects. Moreover, it possesses excellent thermal stability and resists decomposition under high-temperature baking conditions, ensuring long-lasting aroma. Additionally, it is used to synthesize nutty heterocyclic fragrances. For example, benzylidene piperidinol, generated by the condensation reaction between the product and benzaldehyde, presents a blended walnut and almond aroma, which is added to nut-based foods, chocolates and other products to enrich aroma layers.
In the field of daily chemical fragrances, it and its derivatives are adopted to formulate flavors for high-end perfumes, skincare products, detergents and other consumer goods. The synthesized fragrances are characterized by delicate scent, long-lasting retention and non-irritation, fully complying with safety standards for daily chemical products.
N-methyl-3-hydroxypiperidine, obtained via N-alkylation of it, can be compounded with coumarin, ionone and other fragrance raw materials for perfume base note blending. It effectively enhances the mellow texture and lasting time of perfume, creating a soft and enduring scent. Furthermore, 3-acyloxypiperidine derivatives, produced by the acylation reaction between 3-Hydroxypiperidine and fatty acids, emit mixed floral and fruity aromas, which are widely incorporated into flavors for skincare items, body washes, shampoos and other products to optimize user experience.
In the field of tobacco flavors, it acts as a flavor enhancer and fixative. It interacts with nicotine, tar and other components in tobacco to neutralize pungent irritation, enhance the mellow sense of tobacco aroma, and prolong fragrance retention. When mixed with solvents such as propylene glycol and glycerin and then added to tobacco, it enables mild and pleasant aroma release during combustion, reduces harsh odors, and improves overall tobacco quality. Currently, it has been widely applied in the production of mid-to-high-end cigarettes.
1.2 Applications in Resin and Coatings
In the resin and coatings industry, it is primarily used as a key intermediate for the research and production of epoxy resin curing agents, rubber vulcanization accelerators, coating modifiers and other functional products. Its secondary amine and secondary alcohol groups participate in the cross-linking reaction of resins, optimizing core properties including mechanical strength, aging resistance and corrosion resistance. It meets diversified application demands and is widely utilized in construction, automotive, electronic, mechanical and other industrial sectors.
In the area of epoxy resin curing agents, it functions as a high-efficiency room-temperature curing agent. Its secondary amine groups trigger ring-opening reactions with epoxy groups in epoxy resins to form a cross-linked network structure, realizing rapid resin shaping. It features fast curing speed, low curing temperature and superior cured performance. Compared with traditional amine curing agents, epoxy resins cured by it exhibit higher toughness and impact resistance.
Meanwhile, the secondary alcohol groups form hydrogen bonds with hydroxyl groups in epoxy resins, boosting the adhesion and water resistance of cured materials. It is suitable for low-temperature construction scenarios, such as building wall decoration, electronic component encapsulation, and mechanical part coating. In addition, 3-PIPERIDINOL can be compounded with other curing agents including polyamides and aliphatic amines to adjust curing rate and material performance.
For example, compounding with polyamides improves the flexibility and corrosion resistance of cured products, making it ideal for exterior architectural coatings and automotive chassis coatings.In the field of rubber vulcanization accelerators, 3-PIPERIDINOL derivatives such as N-cyclohexyl-3-hydroxypiperidine and N-benzyl-3-hydroxypiperidine serve as high-performance vulcanization accelerators. They can replace conventional thiourea and thiuram accelerators, with advantages of rapid vulcanization, high efficiency and environmental friendliness.
The functional mechanism lies in the reaction between secondary amine groups and double bonds in rubber molecules, which promotes molecular cross-linking and improves the tensile strength, tear resistance and wear resistance of rubber materials. Meanwhile, it reduces the generation of harmful substances during vulcanization, aligning with the green development trend of the industry. Such accelerators are extensively used in the vulcanization processing of natural rubber and synthetic rubber including styrene-butadiene rubber and nitrile rubber, for manufacturing tires, sealing parts, rubber hoses, cables and other rubber products to extend service life and comprehensive performance.
In coating modification, 3-Hydroxypiperidine acts as an adhesion promoter and anti-aging modifier. Its secondary alcohol groups form hydrogen bonds with resin molecules in coatings, strengthening the bonding force between coatings and substrates such as metal, wood and plastic, and preventing peeling and flaking.
Meanwhile, its heterocyclic structure delivers outstanding antioxidant and ultraviolet absorption capabilities, which enhance the ultraviolet aging resistance and weather resistance of coatings and extend service life. Adding a small amount of 3-PIPERIDINOL to water-based coatings can significantly improve adhesion and water resistance, applicable to outdoor architectural and automotive coatings. Its derivatives, when added to powder coatings, optimize fluidity and curing performance, and improve the flatness and gloss of coating films.
1.3 Applications in Chiral Materials and Functional Additives
With the rapid advancement of chiral technology, the market demand for chiral materials in pharmaceuticals, fine chemicals, electronics and other fields continues to grow. As a critical chiral intermediate, 3-PIPERIDINOL and its enantiomers ((R)-3-hydroxypiperidine and (S)-3-hydroxypiperidine) are used for the preparation of chiral catalysts, chiral ligands and chiral functional materials, possessing high industrial application value.
Moreover, 3-PIPERIDINOL is developed as a functional additive for surfactants, antistatic agents, flame retardants and other products, further expanding the application scope of fine chemical products.In the field of chiral catalysts and ligands, 3-PIPERIDINOL derivatives represent an important class of chiral catalytic materials. The chiral centers and heterocyclic structures in their molecules form stable complexes with metal ions such as palladium, platinum and rhodium.
These complexes are widely applied in asymmetric synthesis reactions, including asymmetric hydrogenation, asymmetric epoxidation and asymmetric addition, enabling the high-efficiency and high-selectivity synthesis of chiral compounds for chiral pharmaceuticals, chiral fragrances and chiral materials. For example, chiral ligands derived from (R)-3-hydroxypiperidine via acylation and alkylation can coordinate with palladium ions to catalyze the asymmetric hydrogenation of aromatic ketones, delivering products with an enantiomeric excess (ee) of over 95% and greatly improving the purity and yield of chiral products. Chiral catalysts derived from (S)-3-hydroxypiperidine are applied in the asymmetric epoxidation of olefins, providing an efficient synthetic route for chiral epoxy compounds.
preparation methods
Place 3-hydroxypyridine (1.91g, 0.02mol), a catalyst, and 10ml of distilled water in a hydrogenation kettle. Mix thoroughly and secure the kettle. Replace the air with nitrogen three times, followed by replacing nitrogen with hydrogen three times. Adjust the pressure to 3 MPa and react at 80°C until the pressure no longer decreases. Stop the reaction, allow the temperature to drop to room temperature, slowly release the excess hydrogen, dismantle the kettle, filter the reaction liquid through celite, and dry it to obtain 3-hydroxypiperidine (1.82g) with a yield of 95.29%.
FAQ
What is 3 hydroxypiperidine used for?
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As a piperidine derivative, (S)-1-tert-butoxycarbonyl-3-hydroxypiperidine (1) is an important intermediate with a chiral structure, which has antibacterial, antitumor, and treatment of Alzheimer's disease. It is also one of the important drugs for the treatment of viral infections (including AIDS) and diabetes .
What is 3 hydroxypyridine used for?
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In the agricultural sector, 3-Hydroxypyridine is employed in the formulation of herbicides and fungicides, contributing to improved crop protection and yield. Its ability to chelate metal ions also makes it valuable in analytical chemistry for trace metal analysis.
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