2-Phenyl-1H-indol-1-ol: Properties, Synthesis & Applications

2-Phenyl-1H-indol-1-ol is a structurally distinctive N-hydroxyindole compound bearing a phenyl substituent at the 2-position, making it a valuable intermediate and probe in heterocyclic chemistry and oxidative biology research.

Chemical Name

2-Phenyl-1H-indol-1-ol

SKU

N1060439

Compound Class

N-Hydroxyindole (indolyl hydroxamic derivative)

Core Scaffold

Indole fused bicyclic system with N–OH functionality

Primary Research Utility

Synthetic intermediate, oxidative chemistry probe, heterocyclic building block

Storage Recommendation

Store in a cool, dry, well-ventilated area away from light and moisture (verify with SDS)

Chemical Structure and Key Properties

2-Phenyl-1H-indol-1-ol belongs to the class of N-hydroxyindoles, a family of heterocyclic compounds in which the nitrogen atom of the indole ring bears a hydroxyl group rather than a hydrogen atom. The presence of a phenyl group at the 2-position of the indole scaffold further modulates the electronic character of the ring system, increasing conjugation and influencing both the compound's reactivity and its photophysical properties.

The N–OH bond in N-hydroxyindoles is a defining functional feature. It renders the nitrogen center more electrophilic compared with simple indoles and provides a handle for a range of chemical transformations, including oxidation to the corresponding nitroso or nitro species, and O-functionalization to yield O-acyl or O-sulfonyl derivatives. These characteristics distinguish 2-Phenyl-1H-indol-1-ol from the more commonly encountered 2-phenylindole (the parent N–H compound) and underpin its utility as a reactive intermediate.

Note: Specific physicochemical data such as melting point, molecular weight, logP, and spectroscopic assignments should be verified against the current Certificate of Analysis and Safety Data Sheet supplied with SKU N1060439.

Synthesis and Preparation Routes

N-Hydroxyindoles, including 2-aryl-substituted variants such as 2-Phenyl-1H-indol-1-ol, are typically accessed via one of several established synthetic strategies in the heterocyclic chemistry literature:

• Oxidation of 2-phenylindole: Direct N-oxidation of the parent indole using peracids (e.g., m-CPBA) or other selective oxidants can introduce the N–OH functionality, though selectivity and over-oxidation must be carefully managed.
• Condensation approaches: Cyclization of appropriately substituted phenylhydroxylamines with 1,3-dicarbonyl equivalents or α,β-unsaturated carbonyl compounds can afford N-hydroxyindole products under acid or base catalysis.
• Reductive pathways: Partial reduction of 2-phenylindole N-oxide intermediates offers an alternative route to the N-hydroxyl oxidation state.

The precise synthetic route employed for the material supplied under SKU N1060439 is proprietary. Researchers requiring detailed synthetic protocols or isotopically labeled analogs are encouraged to contact Aladdin Scientific's technical support team.

Review flag: Specific literature citations for each synthetic route should be verified before publication.

Research Applications

2-Phenyl-1H-indol-1-ol and related N-hydroxyindoles have attracted attention across several domains of chemical and biological research:

• Synthetic intermediates: The N–OH group serves as a versatile handle for further derivatization. O-Acylation yields reactive esters capable of acting as electrophilic amination reagents, useful in the synthesis of complex nitrogen-containing natural products and pharmaceuticals.
• Oxidative biology probes: N-Hydroxyindoles can participate in radical and redox chemistry, making them potential probes for studying oxidative stress pathways, reactive nitrogen species, and enzyme-mediated oxidation in biological systems.
• Heterocyclic building blocks: As a 2-arylindole scaffold with an activated nitrogen, this compound can serve as a precursor to oxazines, isoxazolines, and other fused heterocyclic systems through cycloaddition or condensation reactions.
• Medicinal chemistry exploration: The indole core is a privileged scaffold in drug discovery. N-Hydroxylation alters hydrogen-bonding capacity and metabolic stability relative to the parent indole, properties of potential interest in structure–activity relationship studies.

Review flag: Specific biological activity data for 2-Phenyl-1H-indol-1-ol itself are not available in the source material and should not be stated without supporting citations.

Handling, Stability, and Storage

As an N-hydroxyindole, 2-Phenyl-1H-indol-1-ol contains a relatively labile N–O bond that may be susceptible to thermal degradation, photolysis, and reaction with strong oxidizing or reducing agents. The following general precautions are recommended, pending review of the product-specific Safety Data Sheet (SDS):

• Storage: Store in a tightly sealed container under inert atmosphere (nitrogen or argon) in a cool, dark location. Refrigeration at 2–8 °C or freezer storage may extend shelf life; confirm conditions with the SDS for SKU N1060439.
• Light sensitivity: N-Hydroxy compounds can be photosensitive. Amber vials or foil-wrapped containers are advisable during storage and handling.
• Compatibility: Avoid contact with strong acids, bases, and transition-metal oxidants which may promote decomposition or undesired redox reactions.
• Personal protection: Standard laboratory PPE including gloves, eye protection, and a lab coat should be worn. Consult the full SDS for hazard classification and first-aid measures before use.

Review flag: Specific stability data, hazard classifications, and recommended storage temperature for N1060439 must be confirmed from the official SDS before this section is finalized.

Ordering and Product Information

2-Phenyl-1H-indol-1-ol is available from Aladdin Scientific under SKU N1060439. When placing an order, researchers should confirm the following with the Aladdin Scientific sales or technical team:

• Available pack sizes and current pricing
• Purity specification and analytical method (e.g., HPLC, NMR)
• Current stock availability and lead time
• Shipping conditions (temperature-controlled shipping may be required)
• Applicable regulatory documentation (SDS, Certificate of Analysis)

For bulk quantities, custom synthesis inquiries, or questions about specific applications, please contact Aladdin Scientific's technical support. Our team can assist with selection of related indole derivatives and structurally analogous building blocks to support your research program.

Frequently asked questions

What is the difference between 2-Phenyl-1H-indol-1-ol and 2-phenylindole?

2-Phenylindole carries a hydrogen atom on the indole nitrogen (N–H), whereas 2-Phenyl-1H-indol-1-ol has a hydroxyl group on the nitrogen (N–OH). This N-hydroxylation significantly alters the compound's reactivity, hydrogen-bonding properties, and potential for further chemical derivatization compared with the parent N–H indole.

How should 2-Phenyl-1H-indol-1-ol be stored to maintain stability?

As a general precaution for N-hydroxyindole compounds, storage in a sealed container under inert gas (nitrogen or argon), protected from light and moisture, in a cool environment is recommended. Specific storage temperature and conditions for SKU N1060439 should be confirmed by consulting the product's Safety Data Sheet and Certificate of Analysis.

What are the main research applications of 2-Phenyl-1H-indol-1-ol?

2-Phenyl-1H-indol-1-ol is primarily of interest as a synthetic intermediate in heterocyclic chemistry, particularly for accessing O-functionalized N-hydroxyindole derivatives useful in electrophilic amination reactions. It may also serve as a probe in oxidative chemistry studies and as a building block for constructing fused heterocyclic frameworks relevant to medicinal chemistry research.

How do I confirm the purity and identity of the received product?

Each batch of SKU N1060439 from Aladdin Scientific is accompanied by a Certificate of Analysis (CoA) specifying the analytical method and purity result. Researchers are encouraged to review the CoA upon receipt and contact Aladdin Scientific technical support if the data do not meet experimental requirements.

Can 2-Phenyl-1H-indol-1-ol be used as a reference standard in analytical methods?

Depending on the purity grade available, 2-Phenyl-1H-indol-1-ol may be suitable as an analytical reference standard. Researchers should confirm the purity specification, available analytical data (HPLC, NMR, MS), and traceability information with Aladdin Scientific before use in validated analytical methods.

References

1. General reference: Zhdankin, V. V. et al. Chemistry of N-hydroxyindoles and related N-oxy heterocycles. To be verified.
2. General reference: Sundberg, R. J. Indoles. Academic Press, 1996. Standard textbook reference for indole chemistry.
3. Aladdin Scientific. Product datasheet for 2-Phenyl-1H-indol-1-ol, SKU N1060439. Aladdin Scientific, Shanghai.

Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.