3-Methyl-5-(phenylmethoxy)-2-[4-(phenylmethoxy)phenyl]-1H-indole
[CAS# 198479-63-9]

Identification

• Classification: Chemical reagent >> Organic reagent >> Polycyclic compound
• Name: 3-Methyl-5-(phenylmethoxy)-2-[4-(phenylmethoxy)phenyl]-1H-indole
• Synonyms: 5-(Benzyloxy)-2-[4-(benzyloxy)phenyl]-3-methyl-1H-indole
• Molecular Formula: C₂₉H₂₅NO₂
• Molecular Weight: 419.51
• CAS Registry Number: 198479-63-9
• EC Number: 695-298-8
• SMILES: CC1=C(NC2=C1C=C(C=C2)OCC3=CC=CC=C3)C4=CC=C(C=C4)OCC5=CC=CC=C5

Properties

• Density: 1.2±0.1 g/cm³ Calc.^*
• Boiling point: 620.5±55.0 °C 760 mmHg (Calc.)^*
• Flash point: 213.9±21.8 °C (Calc.)^*
• Index of refraction: 1.66 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Risk Statements: H314-H315-H319-H335
• Safety Statements: P260-P261-P264-P264+P265-P271-P280-P301+P330+P331-P302+P352-P302+P361+P354-P304+P340-P305+P351+P338-P305+P354+P338-P316-P319-P321-P332+P317-P337+P317-P362+P364-P363-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin corrosion	Skin Corr.	1B	H314
Eye irritation	Eye Irrit.	2A	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

3-Methyl-5-(phenylmethoxy)-2-[4-(phenylmethoxy)phenyl]-1H-indole is a synthetic organic compound characterized by an indole core substituted at multiple positions with distinct functional groups. The molecule consists of a 1H-indole scaffold bearing a methyl group at the 3-position and two phenylmethoxy (benzyloxy) substituents: one attached directly at the 5-position of the indole ring and the other linked via a para-substituted phenyl ring at the 2-position. This structural arrangement results in a complex, highly aromatic framework with ether linkages.

The indole nucleus is a bicyclic heteroaromatic system composed of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. Indole and its derivatives are widely studied in medicinal chemistry due to their prevalence in natural products and bioactive compounds, including neurotransmitters, hormones, and alkaloids. The substitutions on this indole derivative influence its physicochemical properties, electronic distribution, and potential biological activity.

The phenylmethoxy groups (benzyloxy groups) attached to the indole core and the additional phenyl ring introduce aromatic ether functionalities, which may affect the compound’s lipophilicity and membrane permeability. These groups can also participate in π–π stacking interactions and hydrogen bonding when interacting with biological targets, potentially modulating receptor binding or enzyme inhibition.

The methyl group at the 3-position is a small hydrophobic substituent that can influence steric and electronic characteristics of the molecule. This substitution may affect the compound’s conformational preferences and metabolic stability.

Synthesis of 3-methyl-5-(phenylmethoxy)-2-[4-(phenylmethoxy)phenyl]-1H-indole typically involves multi-step organic transformations, including the construction of the indole ring via Fischer indole synthesis or related methods, selective introduction of methyl and phenylmethoxy substituents through alkylation or etherification reactions, and coupling of the 4-(phenylmethoxy)phenyl group at the 2-position via cross-coupling or electrophilic substitution.

This compound, like many substituted indoles, may be investigated for potential pharmacological properties such as anti-inflammatory, anticancer, or central nervous system activity, given the biological significance of the indole scaffold. The phenylmethoxy groups could enhance binding affinity to various receptors or enzymes by increasing hydrophobic and aromatic interactions.

Characterization techniques for this molecule include nuclear magnetic resonance (NMR) spectroscopy to confirm the structure and substitution pattern, mass spectrometry for molecular weight determination, and infrared (IR) spectroscopy to identify functional groups. High-performance liquid chromatography (HPLC) may be used for purity assessment.

Due to its complex aromatic structure, the compound is expected to have moderate solubility in organic solvents such as dichloromethane, chloroform, or dimethylformamide (DMF), with limited solubility in water.

In summary, 3-methyl-5-(phenylmethoxy)-2-[4-(phenylmethoxy)phenyl]-1H-indole is a multiply substituted indole derivative featuring methyl and benzyloxy groups that contribute to its aromatic and electronic properties. Its synthesis involves strategic functionalization of the indole core, and it is a compound of interest in organic and medicinal chemistry research for its potential biological activities and structural features.

References

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