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1H-Indole, 2-phenyl-, potassium salt (1:1)

Also known as potassium 2-phenylindol-1-ide, 1H-Indole, 2-phenyl-, potassium salt

1H-Indole, 2-phenyl-, potassium salt, also known as potassium 2-phenylindol-1-ide, is a specialized indolide salt with formula C14H10KN and molecular weight 231.33.

Organic chemical compounds Heterocyclic potassium salts

Product identity

CAS number
63467-59-4
Molecular formula
C14H10KN
Molecular weight
231.33 g/mol
Category
Organic chemical compounds
Subcategory
Heterocyclic potassium salts
Common aliases
potassium 2-phenylindol-1-ide, 1H-Indole, 2-phenyl-, potassium salt

Product overview

What is 1H-Indole, 2-phenyl-, potassium salt (1:1)?

1H-Indole, 2-phenyl-, potassium salt is the potassium salt of a 2-phenyl-substituted indole anion, identified as potassium 2-phenylindol-1-ide. Its formula is C14H10KN and its molecular weight is 231.33. The molecule combines an indole-derived fused aromatic system, a phenyl substituent at the 2-position, and potassium as the counterion. This identity distinguishes it from neutral 2-phenylindole and from other metal indolide compounds.

The potassium salt form gives 1H-Indole, 2-phenyl-, potassium salt an ionic character that differs from the corresponding neutral heterocycle. Its conjugate-base centre is associated with the indole nitrogen, while the fused rings and phenyl group provide substantial aromatic character. Consequently, its behaviour can depend strongly on solvent polarity, moisture, temperature, concentration, and the presence of proton donors or electrophilic reaction partners.

In established chemical practice, potassium indolides are used as reactive intermediates, bases, or nucleophilic starting materials in controlled organic synthesis and exploratory research. 1H-Indole, 2-phenyl-, potassium salt may therefore be considered where a preformed potassium indolide is useful for studying N-centred reactivity or for developing transformations involving substituted indole frameworks. Actual suitability depends on the intended reaction and the characteristics of the selected material.

Selection should begin with the required reaction pathway, substrate compatibility, solvent system, and sensitivity to proton transfer. Users should distinguish this potassium salt from 2-phenylindole, potassium indole salts with different substitution patterns, and alkali-metal compounds whose reactivity may not be interchangeable. Practical evaluation should also consider moisture exposure, handling controls, analytical confirmation, and whether the compound’s documented identity matches the intended experimental or manufacturing purpose.

Technical profile

Product properties

Review the product identity and general physical profile before specifying the grade required for your operation.

IUPAC name
potassium 2-phenylindol-1-ide
Category
Organic chemical compounds
Subcategory
Heterocyclic potassium salts
Molecular formula
C14H10KN
Molecular weight
231.33 g/mol

Uses and markets

Applications and industries

The correct product specification depends on the intended process, grade requirements and operating conditions.

Detailed product information

Detailed 1H-Indole, 2-phenyl-, potassium salt (1:1) product information

Reactive indole chemistry and salt-form considerations

1H-Indole, 2-phenyl-, potassium salt is a preformed potassium indolide rather than the neutral 2-phenylindole compound. That distinction matters because the ionic salt can participate differently in proton-transfer, nucleophilic substitution, and electrophile-trapping studies. The 2-phenyl substitution extends the aromatic surface and may influence steric access around the nitrogen-centred reactive site, so reaction outcomes should be established with the actual substrate and solvent system.

Compared with 2-phenylindole, the potassium salt generally represents a more activated nitrogen-centred form for controlled synthetic work. Compared with sodium or lithium analogues, its behaviour should not be assumed identical: counterion coordination, solubility, aggregation, and solvent interactions can alter apparent reactivity. Such differences are especially relevant when transferring a method between salts, changing solvent polarity, or adjusting concentration and temperature.

Applications in synthesis and analytical development

1H-Indole, 2-phenyl-, potassium salt may be evaluated as a specialised starting material for transformations that benefit from a preformed indolide. Potential reaction classes include controlled N-functionalisation, interception by suitable electrophiles, and exploratory construction of substituted indole derivatives. These are application possibilities rather than universal performance claims; the substrate, reagent sequence, atmosphere, and work-up can determine whether the salt is appropriate for a particular route.

In analytical development, the compound can support identity studies, reaction monitoring, or comparative investigations of indole-derived materials. Its formula, potassium content, aromatic structure, and ionic form provide several analytical features to examine, while residual neutral 2-phenylindole or hydrolysis products may complicate interpretation. Method developers should select techniques and sample preparation conditions that preserve or deliberately transform the salt according to the purpose of the measurement.

Behaviour relative to neutral indole compounds

The defining chemical difference between 1H-Indole, 2-phenyl-, potassium salt and neutral 2-phenylindole is deprotonation at the indole nitrogen with potassium charge compensation. This changes acid–base behaviour and can increase readiness for reactions with proton donors or electrophilic partners. It does not mean every reaction will be faster or cleaner, because aggregation, poor dissolution, competing proton sources, and substrate-specific steric effects can control the observed result.

The potassium salt also differs from a simple potassium-containing mixture because its counterion is associated with a specific indolide composition. Comparison with potassium salts of unsubstituted indole or differently substituted indoles should therefore account for the 2-phenyl group’s electronic and steric influence. In formulation or route screening, small changes in solvent, water content, and reagent order may produce meaningful differences in conversion, selectivity, or recoverable product.

Formulation and identification considerations

For 1H-Indole, 2-phenyl-, potassium salt, formulation decisions should focus on maintaining the intended ionic form during preparation and use. Proton-donating solvents, atmospheric moisture, acidic additives, and prolonged exposure to incompatible surfaces may alter the material through protonation or related chemical change. A solvent selected for neutral 2-phenylindole should not automatically be treated as suitable for this potassium salt without practical solubility and stability assessment.

Identity assessment should distinguish the potassium indolide from neutral 2-phenylindole, other alkali-metal indolides, and decomposition or protonation products. A coherent evaluation can combine structural, elemental, and chromatographic evidence selected for the intended purpose. In reaction development, monitoring both disappearance of the starting salt and formation of the desired product is more informative than relying on a single signal or assuming that nominal molecular weight proves complete conversion.

Frequently asked questions

Questions about 1H-Indole, 2-phenyl-, potassium salt (1:1)

How does 1H-Indole, 2-phenyl-, potassium salt differ from 2-phenylindole?

1H-Indole, 2-phenyl-, potassium salt is the deprotonated, potassium-associated form of the 2-phenylindole framework. 2-Phenylindole is neutral, whereas the potassium salt contains an indolide anion balanced by potassium. This difference changes acid–base behaviour, solvent interactions, and potential reactivity toward proton donors and electrophiles. The salt may be useful when a preformed nitrogen-centred reactive species is desired, but it should not be treated as a drop-in replacement for the neutral compound. Solubility, aggregation, reagent compatibility, and work-up can differ substantially. Any substitution between the two should therefore be tested in the exact reaction conditions rather than inferred from their shared aromatic structure.

What reaction behaviour is associated with this potassium indolide?

1H-Indole, 2-phenyl-, potassium salt can be considered a nitrogen-centred nucleophilic or basic reagent in suitable controlled organic reactions. Its behaviour may include proton transfer with compatible donors and reaction with selected electrophiles, potentially enabling N-functionalisation or preparation of further substituted indole compounds. The outcome depends on solvent, temperature, concentration, substrate structure, reagent order, water content, and competing reactive sites. Potassium coordination and aggregation can also influence apparent reactivity. These factors mean that a reaction reported for another indolide, metal salt, or solvent system cannot automatically be transferred. Small-scale route evaluation is appropriate before broader use.

Why does the potassium counterion matter in synthetic work?

The potassium counterion contributes more than a nominal elemental component to the behaviour of 1H-Indole, 2-phenyl-, potassium salt. Ion pairing, coordination, aggregation, and solvation can affect how accessible the indolide nitrogen is and how readily the material dissolves or reacts. These effects may differ from those observed with lithium or sodium analogues, even when the organic portion is unchanged. The counterion can also influence selectivity, work-up behaviour, and the response seen in some analytical methods. Consequently, replacing the potassium salt with another metal indolide should be treated as a chemical change requiring experimental comparison, not merely a convenient substitution.

What solvents should be considered for this compound?

Solvent selection for 1H-Indole, 2-phenyl-, potassium salt should reflect its ionic character and sensitivity to proton donors. Polar aprotic systems may be considered in some synthetic studies because they can support ionic reagents without introducing an intentionally acidic proton source. However, the best solvent depends on the reaction partner, desired selectivity, concentration, temperature, and equipment. Moisture-containing or protic media may protonate the indolide or change its effective concentration, while weakly solvating media may produce suspension or aggregation effects. Solubility and reaction performance should therefore be checked experimentally, with attention to water control and compatibility with the complete reagent set.

How can this salt be distinguished from neutral or altered material?

A useful distinction begins with the expected composition of 1H-Indole, 2-phenyl-, potassium salt: an indole-derived organic anion associated with potassium. Analytical evaluation should be selected to examine the organic structure, potassium presence, molecular composition, and ionic state as appropriate for the purpose. Neutral 2-phenylindole, protonated material, hydrolysis products, and unrelated potassium salts can produce overlapping or misleading observations in a single technique. For that reason, identity assessment is stronger when complementary methods are interpreted together. Reaction monitoring should also examine product formation and possible protonation by-products rather than assuming that disappearance of one starting signal demonstrates the intended transformation.

What factors can affect its suitability for a particular synthesis?

Suitability of 1H-Indole, 2-phenyl-, potassium salt depends on the reaction design rather than on the compound name alone. Important factors include the electrophile or substrate, competing acidic groups, solvent polarity, water content, temperature, concentration, atmosphere, reagent sequence, and the required selectivity. Steric effects from the 2-phenyl substituent may influence access to the reactive nitrogen, while aggregation or limited solubility can affect reproducibility. A method developed with a different indolide should be treated as a starting hypothesis. Practical screening should compare conversion, selectivity, side reactions, and work-up behaviour under conditions representative of the intended application.

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