5-(Benzyloxy)indole
5-(Benzyloxy)indole (CAS: 1215-59-4, C15H13NO, MW: 223.27) is a versatile indole derivative used as a key building block in organic synthesis. It serves as a crucial reactant in various synthetic methodologies, including regioselective C-3 alkenylation, selective debenzylation, and metal-free Friedel-Crafts alkylation. This compound is particularly valuable in the preparation of biologically active molecules, such as protein kinase (PKC) inhibitors and indole/quinoline carbothioic acid amide derivatives.
- IUPAC
- NSC 62895
Organic Synthesis Building Block
5-(Benzyloxy)indole functions as a fundamental building block in complex organic synthesis. Its indole core and benzyloxy substituent offer unique reactivity for constructing sophisticated molecular architectures.
Preparation of Protein Kinase Inhibitors
This compound is employed in the synthetic routes leading to protein kinase (PKC) inhibitors. These inhibitors are crucial in pharmaceutical research for targeting various cellular signalling pathways.
C-3 Alkenylation Reactions
It acts as a reactant in regioselective and stereoselective morpholine-catalyzed direct C-3 alkenylation reactions with α,β-unsaturated aldehydes, enabling the formation of new carbon-carbon bonds at the indole C-3 position.
Selective Debenzylation
5-(Benzyloxy)indole can participate in selective debenzylation processes using catalysts like SiliaCat-palladium under mild conditions, facilitating the removal of benzyl protecting groups.
Friedel-Crafts Alkylation
The compound is utilized as a reactant in metal-free Friedel-Crafts alkylation reactions, providing a greener approach to C-C bond formation on aromatic systems.
| Molecular weight | 223.27 |
|---|---|
| Empirical formula | C15H13NO |
| Assay | 95% |
| Impurities tested | 5% various solvents of crystallization |
| Application | • Reactant in regio- and stereoselective morpholine-catalyzed direct C-3 alkenylation with α,β-unsaturated aldehydes• Reactant in selective debenzylation of protective groups using SiliaCat-palladium under mild reaction conditions• Reactant in metal-free Friedel-Crafts alkylation reactions• Reactant in preparation of protein kinase (PKC) inhibitors• Reactant in preparation of indole/quinoline carbothioic acid amide derivatives |
| Melting point | 100-104 °C(lit.) |
Documentation
Every batch ships with a Certificate of Analysis covering assay, identity and purity; the grade is confirmed against your enquiry. Safety Data Sheets and technical data sheets are available on request.
Supply & logistics
Samples for technical evaluation; bulk MOQ by grade and packaging. In-stock material ships in 7–10 working days, worldwide, with full export documentation.
What is 5-(Benzyloxy)indole used for?
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5-(Benzyloxy)indole is used as a building block in organic synthesis, particularly in preparing protein kinase (PKC) inhibitors, for regioselective C-3 alkenylation, selective debenzylation, and metal-free Friedel-Crafts alkylation reactions.
What is the CAS number and chemical formula for 5-(Benzyloxy)indole?
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The CAS number for 5-(Benzyloxy)indole is 1215-59-4, and its empirical formula is C15H13NO.
What grade and purity does Tech Serve Solutions supply?
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Tech Serve Solutions supplies 5-(Benzyloxy)indole with an assay of 95%. This product is not represented as USP, BP, or EP grade.
What are the hazards associated with 5-(Benzyloxy)indole and how should it be handled?
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5-(Benzyloxy)indole is classified under WGK 2. Handle with appropriate personal protective equipment in a well-ventilated area, avoiding contact with skin, eyes, and clothing. Refer to the Safety Data Sheet (SDS) for detailed handling information.
How is 5-(Benzyloxy)indole packed and shipped?
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5-(Benzyloxy)indole is carefully packed according to industry standards to ensure safe transit and is available for export globally by Tech Serve Solutions.
How can I request a sample or quote for 5-(Benzyloxy)indole?
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To request a sample or obtain a quote for 5-(Benzyloxy)indole, please contact our sales team through the website or by phone.
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