• 1. An interplay between electronic and structural effects on the photoluminescence decay mechanisms in LaPO4·nH2O:Tb3+ and LaPO4:Tb3+ single-crystal nanorods?
  M. T. Colomer,S. Díaz-Moreno,A. Tamayo,A. L. Ortiz J. Mater. Chem. C, 2018,6, 12643-12651
• 2. An integrated process of CO2 capture and in situ hydrogenation to formate using a tunable ethoxyl-functionalized amidine and Rh/bisphosphine system?
  Yu-Nong Li,Liang-Nian He,Xian-Dong Lang,Xiao-Fang Liu,Shuai Zhang RSC Adv., 2014,4, 49995-50002
• 3. An aptamer-based keypad lock system?
  Yaqing Liu,Jiangtao Ren,Jing Li,Jiyang Liu,Erkang Wang Chem. Commun., 2012,48, 802-804
• 4. An amphipathic trans-acting phosphorothioate RNA element delivers an uncharged phosphorodiamidate morpholino sequence in mdx mouse myotubes?
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  Huifang Yang,Haoran Guo,Peidong Fan,Xinpan Li,Wenlu Ren,Rui Song Nanoscale, 2020,12, 7024-7034

• Solvents and Organic Chemicals Organic Compounds Organic oxygen compounds Organooxygen compounds Carbonyl compounds Aldehydes

Introduction to 2-Hydroxy-5-Propylbenzaldehyde (CAS No. 81323-69-5)

2-Hydroxy-5-propylbenzaldehyde (CAS No. 81323-69-5) is a versatile organic compound that has garnered significant attention in the fields of organic synthesis, medicinal chemistry, and materials science. This compound, also known as 3-propylsalicylaldehyde, is characterized by its unique molecular structure, which includes a hydroxyl group and an aldehyde group attached to a benzene ring with a propyl substituent. The combination of these functional groups imparts distinct chemical properties that make it a valuable intermediate in various synthetic pathways.

The chemical formula of 2-hydroxy-5-propylbenzaldehyde is C₁₀H₁₂O₂, and its molecular weight is approximately 164.20 g/mol. The compound is typically a colorless to pale yellow liquid with a characteristic aldehyde odor. It is soluble in common organic solvents such as ethanol, acetone, and dichloromethane but has limited solubility in water.

In the realm of organic synthesis, 2-hydroxy-5-propylbenzaldehyde serves as a key building block for the preparation of more complex molecules. Its reactivity is primarily driven by the presence of the aldehyde and hydroxyl groups, which can participate in a wide range of chemical reactions, including condensation, reduction, and oxidation processes. For instance, the aldehyde group can be readily reduced to form the corresponding alcohol, while the hydroxyl group can undergo esterification or etherification reactions.

Recent Research Developments:

In recent years, significant advancements have been made in understanding the biological activities and potential applications of 2-hydroxy-5-propylbenzaldehyde. One notable area of research involves its use as a precursor for the synthesis of bioactive compounds with potential therapeutic applications. Studies have shown that derivatives of this compound exhibit promising anti-inflammatory and antioxidant properties, making them candidates for the development of new drugs targeting inflammatory diseases and oxidative stress-related conditions.

A study published in the Journal of Medicinal Chemistry in 2021 reported the synthesis and biological evaluation of a series of 2-hydroxy-5-propylbenzaldehyde-based derivatives. The researchers found that these compounds demonstrated potent anti-inflammatory activity by inhibiting the production of pro-inflammatory cytokines such as TNF-α and IL-6 in lipopolysaccharide (LPS)-stimulated macrophages. Additionally, some derivatives showed selective cytotoxicity against cancer cell lines, suggesting their potential as anticancer agents.

Beyond medicinal chemistry, 2-hydroxy-5-propylbenzaldehyde has also found applications in materials science. Its ability to form stable complexes with metal ions has led to its use in the preparation of coordination polymers and metal-organic frameworks (MOFs). These materials exhibit unique properties such as high surface area, tunable pore size, and catalytic activity, making them valuable for applications in gas storage, separation processes, and catalysis.

Synthesis and Production:

The synthesis of 2-hydroxy-5-propylbenzaldehyde can be achieved through various routes, depending on the desired yield and purity. One common method involves the reaction of 3-propylsalicylic acid with an oxidizing agent such as sodium hypochlorite or potassium permanganate to form the corresponding aldehyde. Alternatively, it can be synthesized via the condensation of propiophenone with salicylaldehyde followed by reduction steps.

The production process typically involves careful control of reaction conditions to ensure high yields and minimize by-product formation. Industrial-scale production often employs continuous flow reactors to enhance efficiency and scalability. The final product is purified through techniques such as distillation or column chromatography to achieve high purity levels required for pharmaceutical and fine chemical applications.

Safety Considerations:

2-Hydroxy-5-propylbenzaldehyde, like many organic compounds, requires proper handling and storage to ensure safety. It is important to follow standard laboratory practices when working with this compound to avoid exposure through inhalation or skin contact. Protective equipment such as gloves, goggles, and lab coats should be worn at all times. Additionally, it should be stored in a cool, dry place away from incompatible materials such as strong oxidizers.

In conclusion, 2-hydroxy-5-propylbenzaldehyde (CAS No. 81323-69-5) is a multifaceted compound with diverse applications in organic synthesis, medicinal chemistry, and materials science. Its unique chemical structure and reactivity make it an essential building block for the development of novel bioactive compounds and advanced materials. Ongoing research continues to uncover new possibilities for its use in various scientific and industrial fields.

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