N-Boc-5-methoxyindole
N-Boc-5-methoxyindole (CAS: 99275-47-5), with the molecular formula C14H17NO3 and a molecular weight of 247.29 g/mol, is a key indole building block. This tert-butoxycarbonyl protected derivative serves as a versatile reactant in complex organic synthesis. Its applications span various advanced chemical transformations, including asymmetric alkylations and palladium-catalyzed coupling reactions, making it valuable in the development of pharmaceuticals and novel organic compounds.
- IUPAC
- 5-Methoxyindole-1-carboxylic acid tert-butyl ester,N-(tert-Butoxycarbonyl)-5-methoxyindole
- Synonyms
- 5-Methoxyindole-1-carboxylic acid tert-butyl esterN-(tert-Butoxycarbonyl)-5-methoxyindole
Asymmetric Friedel-Crafts Alkylation
N-Boc-5-methoxyindole is utilised as a substrate in asymmetric intramolecular Friedel-Crafts alkylation reactions, facilitating the synthesis of chiral indole derivatives.
Palladium-Catalyzed Carboaminoxylation
It serves as a precursor in palladium-catalyzed carboaminoxylations, reacting with arylboronic acids and TEMPO catalyst to form complex molecular architectures.
Fluorescent Nucleoside Synthesis
The compound is employed in the synthesis of fluorescent pyrimidopyrimidoindole nucleosides via Suzuki-Miyaura coupling reactions.
Amino Acid Synthesis
N-Boc-5-methoxyindole is a building block for novel conformationally restricted beta- and gamma-amino acids, important in peptide and medicinal chemistry.
DNA Minor Groove Alkylating Agents
It is a reactant in the preparation of DNA minor groove alkylating agents, designed as stable amine-based prodrugs for targeted tumor release.
| Molecular weight | 247.29 |
|---|---|
| Empirical formula | C14H17NO3 |
| Assay | 97% |
| Application | Reactant for preparation of:• Asymmetric intramolecular Friedel-Crafts alkylation reaction1• Palladium-catalyzed carboaminoxylations with arylboronic acids and TEMPO catalyst2• Fluorescent pyrimidopyrimidoindole nucleosides via Suzuki-Miyaura coupling reaction3• Novel conformationally restricted β- and γ-amino acids4• 2-(Indolyl) borates, silanes, and silanols5• DNA minor groove alkylating agents as stable amine-based prodrugs designed for tumor-specific release6 |
| Melting point | 75-79 °C |
Hazard statements
- H301Toxic if swallowed
- H319Causes serious eye irritation
Precautionary statements
- P301IF SWALLOWED
- P305IF IN EYES
| Protective equipment | dust mask type N95 (US), Eyeshields, Faceshields, Gloves |
|---|---|
| Transport (UN / ADR) | UN 2811 6.1 / PGIII |
| Water hazard class (WGK, DE) | 3 |
| Hazard codes (EU) | Xn |
| Risk statements (R) | 22-36 |
| Safety statements (S) | 26 |
Hazard information is provided for guidance. Always consult the product Safety Data Sheet (SDS), available on request, before handling.
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 N-Boc-5-methoxyindole primarily used for?
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N-Boc-5-methoxyindole is primarily used as a versatile building block and reactant in complex organic synthesis, particularly in the preparation of pharmaceuticals and novel organic compounds through various advanced chemical transformations.
What are the CAS number and molecular formula of N-Boc-5-methoxyindole?
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The CAS number for N-Boc-5-methoxyindole is 99275-47-5, and its molecular formula is C14H17NO3.
What grade and purity does Tech Serve Solutions supply?
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Tech Serve Solutions supplies N-Boc-5-methoxyindole with a minimum assay of 97%. This product is typically supplied for research and chemical synthesis purposes and is not represented as USP, BP, or EP grade.
What are the primary hazards associated with N-Boc-5-methoxyindole?
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N-Boc-5-methoxyindole is classified as Danger, with hazard statements H301 (Toxic if swallowed) and H319 (Causes serious eye irritation). Appropriate personal protective equipment, including a dust mask (type N95), eyeshields, face shields, and gloves, should be used when handling this substance. Refer to the Safety Data Sheet for full handling instructions.
How is N-Boc-5-methoxyindole typically packed, shipped, and exported?
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N-Boc-5-methoxyindole is packed according to international shipping regulations for hazardous materials, such as UN 2811, Class 6.1, Packing Group III. Tech Serve Solutions exports this chemical globally to meet the needs of research institutions and industries.
How can I request a quote or sample of N-Boc-5-methoxyindole?
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To request a quote or a sample of N-Boc-5-methoxyindole, please contact our sales team via the website or direct email, providing your specific requirements and shipping details.
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