6-苄氧基吲哚化学性质熔点:116-119°C沸点:411.6±20.0°C(Predicted)密度:1.196±0.06g/cm3(Predicted)储存条件:2-8°C溶解度:Chloroform(Slightly)Chemicalbook,DiethylEther(Slightly),Ethanol(Slightly),EthylAceta酸度系数(pKa):17.17±0.30(Predicted)形态:crystalline颜色:yellowtobrown
*The following content is generated by AI and is for reference only.
6-Benzyloxyindole is a specialized organic compound widely utilized in the fields of medicinal chemistry and synthetic organic research. Its chemical identity is defined by the molecular formula C15H13NO2, representing an indole core substituted with a benzyloxy group at the sixth position. The substance is cataloged under CAS Registry Number 4978-02-5, which serves as its unique identifier for chemical databases and regulatory compliance. Structurally, this molecule features a bicyclic aromatic system where the nitrogen atom resides within the five-membered pyrrole ring, while the oxygen atom of the benzyloxy ether linkage connects to the benzene ring of the indole framework. This specific substitution pattern is crucial for modulating electronic properties and steric hindrance during subsequent chemical transformations.
The primary application of 6-Benzyloxyindole lies in its role as a versatile intermediate for the synthesis of complex bioactive molecules. It is frequently employed as a building block in the development of pharmaceutical agents targeting the central nervous system, including potential antidepressants, antipsychotics, and analgesics. The benzyloxy group acts as a robust protecting group for the hydroxyl functionality, allowing chemists to perform selective reactions on other parts of the indole scaffold without interference. Once the desired structural modifications are complete, the benzyloxy moiety can be efficiently removed via hydrogenolysis or acidic conditions to reveal the free phenolic hydroxyl group, yielding valuable 6-hydroxyindole derivatives. Furthermore, these compounds serve as essential precursors in the total synthesis of alkaloids and natural products possessing significant pharmacological activities. Researchers also utilize it in material science studies to explore novel optical properties or ligand design for metal coordination complexes. Due to its reactivity profile, high purity grades are often required for rigorous laboratory applications. As a key component in drug discovery pipelines, 6-Benzyloxyindole facilitates the rapid generation of diverse libraries, accelerating the identification of lead compounds for therapeutic intervention. Its availability from major chemical suppliers ensures accessibility for academic institutions and industrial laboratories engaged in advanced organic synthesis projects.
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