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Indophenol

Indophenol is a synthetic organic compound classified as a quinone imine, with the molecular formula C₁₂H₉NO₂ and systematic name 4-[(4-hydroxyphenyl)imino]cyclohexa-2,5-dien-1-one.^[1] This deep blue dye serves as the parent structure for the indophenol family of dyes, which are characterized by their intense color and redox properties.^[2] It is primarily recognized for its role in the Berthelot reaction, a colorimetric assay where ammonia reacts with phenol under alkaline oxidizing conditions to form indophenol, enabling sensitive detection of ammonium ions in water, soil, biological fluids, and other samples at concentrations as low as parts per billion.^[3] The compound exhibits a reddish-blue hue in solid form, with a melting point exceeding 300°C and a density of approximately 1.18 g/cm³, reflecting its stability and crystalline nature.^[4] Indophenol can also be synthesized through the oxidation of p-aminophenol or related precursors, though the Berthelot method remains the most common route in analytical contexts.^[5] Beyond ammonia quantification, it finds applications in detecting paracetamol via colorimetry and as a reagent in biochemical assays.^[1] Indophenol dyes, including derivatives like indophenol blue, have historical roots in the mid-19th century and are employed in hair dyes, photographic films, liquid crystal displays, and as pH indicators due to their color changes upon reduction from blue (oxidized) to colorless (reduced) forms.^[6] In biological research, related chlorinated variants such as 2,6-dichlorophenolindophenol are used to probe electron transport chains in chloroplasts and mitochondria, highlighting the compound's versatility in redox studies.^[7] Safety considerations include its classification as a potential irritant, necessitating proper handling in laboratory settings.^[8]

Chemical Structure and Properties

Molecular Structure

Indophenol possesses the general molecular formula \ce{OC6H4NC6H4OH}, corresponding to \ce{C12H9NO2}, and features a para-quinone imine architecture formed by the linkage of a benzoquinone moiety to a phenolate group via an imine bond.^[1]^[4] The core structure includes a cyclohexadienedione ring (benzoquinone) where one carbonyl is replaced by the imine functionality \ce{(C=N)}, connecting to a benzene ring bearing a phenolic hydroxyl group at the para position relative to the nitrogen atom.^[1]^[4] This arrangement establishes an extended conjugated \pi-electron system spanning the quinone, imine, and phenyl rings, which absorbs visible light and imparts the characteristic deep blue coloration to the compound.^[4]^[9] The phenolic hydroxyl group further enhances the chromophoric properties by participating in the delocalization of electrons within the conjugated framework.^[4] Derivatives exhibit variations in substitution, such as indophenol blue (\ce{C18H16N2O}), which incorporates a naphthoquinone imine core coupled at the imine nitrogen to a 4-(dimethylamino)phenyl substituent derived from N,N-dimethylaniline.^[10]

Physical Properties

Indophenol typically appears as a reddish-blue powder in its solid form.^[4] In solution, it manifests as a deep blue dye, exhibiting metachromatic properties that cause color shifts in different solvents—for instance, appearing red in non-polar solvents like diethyl ether and blue in polar environments.^[11] The compound is poorly soluble in water but dissolves readily in organic solvents such as ethanol.^[4] Its molecular weight for the parent indophenol (C₁₂H₉NO₂) is 199.21 g/mol.^[4] Spectroscopically, the oxidized form displays maximal UV-Vis absorption around 630 nm, enabling its use in quantitative assays.^[12] Indophenol has a melting point above 300 °C and generally decomposes before melting; it is sensitive to light exposure during preparation and to reducing agents.^[4]^[2] The blue coloration in solutions stems from its extended conjugated structure.

Chemical Properties

Indophenol exhibits significant redox activity, primarily functioning as an electron acceptor in its oxidized form, which appears blue due to the conjugated quinone imine structure.^[13] This oxidized form can be reduced to the colorless leuco-indophenol, a process that involves the addition of two electrons and two protons, as represented by the equation:

\text{Oxidized indophenol} + 2e^- + 2H^+ \rightarrow \text{leuco-indophenol}

^[14] The quinone imine core of indophenol enables reversible one-electron transfers, allowing stepwise reduction through semiquinone intermediates before full conversion to the leuco form.^[15] This redox behavior makes indophenol suitable for brief applications in redox assays, where color changes signal electron transfer events.^[13] Regarding stability, indophenol is prone to decomposition in alkaline conditions, where hydroxide ions catalyze the hydrolysis of the imine bond through nucleophilic addition to the imine carbon, followed by cleavage of the intermediate carbinolamine.^[16] This reaction limits the longevity of indophenol solutions in basic media, with reactivity influenced by substituents on the aromatic rings.^[16] In contrast, the compound shows greater resilience in neutral or acidic environments, though overall stability depends on the specific derivative.^[17] Indophenol demonstrates pH sensitivity, with its color shifting from red in neutral aqueous solutions to blue in alkaline media, a change attributed to deprotonation of phenolic groups and alterations in the chromophore.^[18] This property allows indophenol to function as a pH indicator over certain ranges, typically around pH 8–10, where the transition provides visual detection of acidity or alkalinity variations.^[18] The pH-dependent color arises from the protonation states affecting the extended conjugation in the quinone imine system.^[2]

Synthesis

Berthelot Reaction

The Berthelot reaction, first described by French chemist Marcellin Berthelot in 1859, represents a foundational oxidative synthesis route for indophenol, involving the condensation of ammonia with phenol under alkaline oxidizing conditions. Originally devised as a qualitative test for ammonia detection, this method produces indophenol as a deeply colored blue product, marking one of the earliest applications of oxidative coupling in organic chemistry. The primary reactants are ammonia (NH₃), phenol (C₆H₅OH), and sodium hypochlorite (NaOCl) as the oxidant, with the reaction proceeding in an alkaline medium to promote deprotonation and electrophilic activation; alternatively, chloramine-T can substitute for NaOCl to generate the active chlorinating species in situ.^[19] The mechanism unfolds in three sequential steps, as elucidated through kinetic and spectrophotometric analyses. Initially, hypochlorite ion (OCl⁻) reacts with ammonia at basic pH to form monochloramine (NH₂Cl), a key electrophilic intermediate. This monochloramine then chlorinates the ortho or para position of phenoxide ion, yielding a transient species such as p-benzoquinone monochlorimide via nucleophilic attack and rearrangement. Finally, the monochlorimide couples with a second phenoxide molecule through electrophilic aromatic substitution to form the indophenol structure, characterized by its quinonoid-imine linkage. This pathway ensures selective formation of the para-substituted indophenol isomer under controlled conditions. Optimal reaction conditions include room temperature (20–25°C) and a pH of 10–12, achieved via addition of sodium hydroxide or carbonate buffers, to maximize intermediate stability and minimize hydrolysis side reactions. Sodium nitroprusside (Na₂[Fe(CN)₅NO]) serves as an effective catalyst, typically at micromolar concentrations, by facilitating electron transfer and accelerating color development to completion within 5–15 minutes, a significant improvement over uncatalyzed variants. The overall process can be summarized by the simplified equation:

\ce{NH3 + 2 C6H5OH + NaOCl ->[pH 10-12, Na2[Fe(CN)5NO]] C6H4(=O)-NH-C6H4-OH + NaCl + H2O}

where the product is the blue indophenol dye.^[20] Yield and purity in the Berthelot reaction are influenced by reagent stoichiometry, with equimolar ratios of ammonia to phenol and slight excess of hypochlorite (1.2–1.5 equivalents) favoring near-quantitative conversion (>90%) for ammonia concentrations up to 1 mM, though higher levels may promote polychlorination byproducts. The intensity of the resulting blue coloration, arising from the extended conjugation in indophenol, is linearly proportional to ammonia input, with the dye exhibiting a high molar extinction coefficient (approximately 5 × 10⁴ L mol⁻¹ cm⁻¹ at 630 nm), enabling sensitive detection; impurities like heavy metals or excess oxidant can quench the color, necessitating purification steps such as extraction for isolated synthesis.^[19]

Oxidative Coupling Methods

Oxidative coupling methods represent a versatile class of synthetic routes for indophenols, involving the direct reaction between phenols and anilines (or their derivatives) under oxidizing conditions to form the characteristic quinone imine structure. These approaches typically proceed via the formation of radical intermediates from the aniline and phenol components, followed by coupling and subsequent oxidation, bypassing the ammonia-mediated pathway of the Berthelot reaction. Common oxidants include molecular oxygen, persulfates, or quinones, enabling the preparation of both unsubstituted and substituted indophenols with good selectivity.^[21]^[22] A specific variant utilizes benzoquinone as the oxidant in the reaction with p-aminophenol, where the quinone acts both as an electron acceptor and coupling partner to yield indophenol through nucleophilic addition and tautomerization. This method is particularly effective in aqueous or alcoholic media at ambient temperatures, often requiring no additional catalysts. Alternatively, electrochemical oxidation facilitates the coupling by applying an anodic potential to generate the necessary radicals from phenol and aniline mixtures, typically in solvents like hexafluoroisopropanol with conductive salts, at temperatures around 50°C and current densities of 1–50 mA/cm².^[23] These reactions are generally conducted in acidic, neutral, or alkaline media, with temperatures ranging from 20–80°C; catalysts such as copper salts can enhance rates in neutral conditions by promoting radical formation. For instance, sodium persulfate in the presence of sodium carbonate serves as a robust oxidant for coupling substituted phenols (e.g., 2,4-dichloro-3-methyl-6-acetamidophenol) with aniline derivatives (e.g., 4-N,N-diethyl-2-aminotoluene hydrochloride) in methanol-water mixtures at 0–room temperature, yielding indophenol derivatives as red solids after recrystallization.^[22]^[21] A representative example is the synthesis of indophenol blue, achieved by oxidative coupling of N,N-dimethyl-p-phenylenediamine with α-naphthol using chemical oxidants like ferricyanide or enzymatic systems, though non-enzymatic variants employ air or persulfate in alkaline media at room temperature to produce the intensely blue product.^[24] The general reaction can be represented as:

\mathrm{C_6H_5NH_2 + HO-C_6H_4-OH + [O] \rightarrow OC_6H_4=NC_6H_4OH}

These methods offer advantages such as higher yields (often 70–90% for substituted variants) and greater flexibility for introducing substituents on the aromatic rings, without reliance on ammonia as a reagent.^[22]

Analytical Applications

Ammonia Detection

The indophenol method utilizes the formation of indophenol blue via the Berthelot reaction for the qualitative and quantitative detection of ammonia in environmental samples.^[25] In this approach, a sample is mixed with alkaline phenol and sodium hypochlorite, which react with ammonia to produce a characteristic blue indophenol dye; the intensity of the blue color serves as a qualitative indicator of ammonia presence.^[25] For quantitative analysis, the indophenol blue is measured spectrophotometrically at approximately 630 nm, where absorbance follows Beer's law, allowing direct correlation to ammonia concentration over a linear range typically from 0.01 to 2.0 mg/L NH₃-N.^[12] This method achieves a detection limit of about 0.01 ppm ammonia, making it suitable for trace-level monitoring in water and air.^[25] Potential interferences from amines and other nitrogenous compounds are mitigated through sample pretreatment, such as distillation into boric acid, to isolate ammonia prior to reaction.^[25] First described by Berthelot in 1859, the indophenol method has been a standard technique for ammonia analysis in water and air since the late 19th century, evolving from manual colorimetric assays to support environmental quality assessments. In modern applications, automated flow injection analysis systems integrate the protocol for high-throughput environmental monitoring, enabling rapid, continuous determination of ammonia in natural waters with minimal sample handling.^[26]

Urea and Other Determinations

The determination of urea using indophenol relies on the enzymatic hydrolysis of urea to ammonia and carbon dioxide by urease, followed by the reaction of the liberated ammonia with phenol and hypochlorite in the Berthelot reaction to form a blue indophenol dye, which is quantified colorimetrically at approximately 570-640 nm.^[27] This indirect approach leverages the sensitivity of indophenol formation to ammonia, adapting the direct ammonia assay for urea analysis.^[28] In the standard protocol, a sample such as serum, plasma, or urine is incubated with urease to generate ammonia quantitatively from urea; the mixture is then treated with alkaline phenol and sodium hypochlorite (or an alternative oxidant like nitroprusside-catalyzed hypochlorite) to produce the indophenol complex, with absorbance measured after color development.^[29] This Berthelot adaptation with urease pre-incubation is widely used in clinical laboratories to measure blood urea nitrogen (BUN) or urinary urea, serving as a key indicator of kidney function and glomerular filtration rate.^[30] The method's linearity typically spans 0.5-50 mg/L urea, offering sufficient sensitivity for routine diagnostics without requiring advanced instrumentation.^[31] Adaptations of the indophenol method extend to other nitrogenous compounds by generating ammonia precursors. For cyanide, the analyte is first oxidized to cyanate with hypochlorite, then hydrolyzed under acidic conditions to release ammonia, which undergoes the standard indophenol reaction for quantification in environmental or industrial samples.^[32] Similarly, paracetamol (acetaminophen) is determined after alkaline hydrolysis to p-aminophenol, followed by oxidation with hypochlorite to form an intermediate that couples in the indophenol reaction, enabling detection in pharmaceutical or biological matrices.^[33] This indophenol-based approach for urea and related determinations provides a cost-effective, colorimetric alternative to more complex enzymatic kits (e.g., those using glutamate dehydrogenase), with high specificity from the urease step and minimal interference when optimized, making it suitable for resource-limited settings.^[34]

Other Uses

Dye Applications

Indophenol dyes emerged as part of the mid-19th-century synthetic dye revolution, marking one of the early commercial successes in the burgeoning industry that transformed textile coloring from natural to artificial sources. Initially applied to cotton and wool fabrics through oxidative processes, these deep blue compounds provided vibrant hues during an era when synthetic dyes like mauveine had just paved the way for mass production.^[35] As dyes, indophenols exhibit moderate light fastness, requiring stabilizers such as copper(II) ions to prevent rapid fading, and are typically applied via oxidation dyeing, where leuco forms are oxidized in air or chemical baths to develop the final color on fibers. This process enhances adhesion to substrates like wool and cotton, though their instability limited long-term durability compared to later azo dyes. The blue coloration arises from the extended conjugated system in their quinone imine structure.^[35] In modern applications, indophenols remain prominent in hair coloring, particularly for achieving blue tones in oxidative and semi-permanent formulations, where they couple with phenols or naphthols during application to form stable, temporary shades that wash out gradually. These dyes are synthesized in situ on the hair shaft, offering customizable intensity without permanent alteration, and are staples in commercial products for their bright, non-metallic blues.^[36]^[37] Industrially, indophenol blue variants, such as C.I. Solvent Blue 22, find use in color photography and dye diffusion thermal transfer printing, where their solubility and color strength suit imaging processes. While direct textile use has become obsolete, they serve as intermediates in sulfur dye production for enhanced shade development.^[35] Environmentally, indophenol dyes pose biodegradability challenges due to their persistent aromatic structures, contributing to water toxicity by increasing coloration and harming aquatic life, such as fish and zooplankton, in effluent discharges. Advanced treatments like photocatalysis are explored to mitigate their release from textile and hair dye industries.^[38]

Biochemical and Redox Roles

Indophenol and its derivatives, particularly 2,6-dichlorophenolindophenol (DCPIP), play significant roles in biochemical assays due to their redox properties. In the determination of vitamin C content, DCPIP serves as an oxidizing agent that is decolorized upon reduction by ascorbic acid, allowing for the quantification of antioxidant capacity through titration or spectrophotometric methods.^[39] This reaction proceeds in a 1:1 stoichiometric manner, where the blue oxidized form of DCPIP turns colorless as it accepts electrons from ascorbic acid, providing a simple and reliable measure of vitamin C levels in biological samples such as fruit juices and tissues.^[40] DCPIP is also widely employed in assays for enzyme activity, notably in monitoring NADH dehydrogenase function. In these assays, the enzyme transfers electrons from NADH to DCPIP, reducing the dye and enabling the measurement of electron transfer rates via the decrease in absorbance at 600 nm.^[41] This approach is particularly useful for characterizing mitochondrial or bacterial NADH:ubiquinone oxidoreductase complexes, where DCPIP acts as an artificial electron acceptor to assess kinetic parameters like V_max and K_M without interference from downstream respiratory chain components.^[42] As a redox mediator, indophenol derivatives facilitate electron transfer in various biological and electrochemical systems, with DCPIP exhibiting a standard reduction potential of approximately +0.22 V versus the standard hydrogen electrode (SHE).^[43] In microbial fuel cells, indophenol compounds enhance electricity generation by shuttling electrons from microbial metabolism to the anode, improving coulombic efficiency in systems utilizing substrates like glucose or acetate.^[44] Similarly, in photosynthesis studies, DCPIP is used in the Hill reaction to demonstrate light-dependent electron transport in isolated chloroplasts; illumination reduces DCPIP from blue to colorless as electrons from water splitting are captured, confirming the non-cyclic photophosphorylation pathway.^[45]

Indophenol Derivatives

Indophenol derivatives are structural variants of the core indophenol scaffold, featuring substitutions on the phenolic or anilino rings that modify their chemical and spectral properties. The parent unsubstituted compound, known as phenolindophenol, has the molecular formula C₁₂H₉NO₂ and is characterized by a quinone imine linkage between a benzoquinone and a 4-aminophenol moiety. This parent structure is less commonly used due to its poor stability, particularly in aqueous solutions where it readily decomposes.^[46] Nomenclature for these derivatives typically reflects the positions of substituents relative to the phenolic hydroxyl group and the anilino nitrogen, as seen in systematic names like 2,6-dichlorophenolindophenol, which specifies ortho-chlorine atoms on the phenolic ring. A well-known example is indophenol blue (C₁₈H₁₆N₂O), derived from N,N-dimethylaniline coupled with a naphthoquinone imine, featuring a dimethylamino group on the anilino ring that imparts intense blue coloration. This derivative is employed in colorimetric assays for ammonia detection via the Berthelot reaction variant.^[47]^[48]^[10] Another key derivative is 2,6-dichlorophenolindophenol (DCPIP), with the formula C₁₂H₆Cl₂NO₂, where chlorine atoms at the 2 and 6 positions on the phenolic ring provide enhanced chemical stability compared to the unsubstituted parent, making it suitable for prolonged use in redox titrations. Substitutions with electron-withdrawing groups, such as halogens in DCPIP or nitro groups in nitro-indophenols, influence the electronic structure, leading to shifts in the absorption spectra; for instance, spectrophotometric studies of various substituted indophenols show variations in peak wavelengths due to these effects.^[49]

Indamine and Indaniline Analogues

Indamines represent a class of nitrogen-containing organic dyes structurally analogous to indophenols, characterized by a quinonoid system featuring a central C=N linkage and lacking the characteristic phenolic oxygen atom found in indophenols. The parent indamine, often denoted as having the formula C₁₂H₁₀N₂, arises as a reduced form with a prominent C-NH connectivity, typically synthesized through the aerial oxidation of aniline in the presence of mild oxidants. These compounds form intensely colored salts, predominantly green, which were among the earliest synthetic dyes developed in the mid-19th century.^[50]^[51] Historical commercialization of indamines occurred alongside indophenols during the late 19th century, with examples like indamine blue emerging as basic fabric dyes valued for their vibrant hues but limited by poor lightfastness. Unlike indophenols, indamines exhibit altered solubility profiles, often requiring acidic conditions to form stable dye salts, and their color fastness is generally inferior, leading to fading upon exposure to light or alkali. These properties stem from the absence of the stabilizing quinone oxygen, resulting in a more reactive chromophore prone to reduction.^[50]^[51] Indanilines, closely related variants of indamines, incorporate additional NH₂ groups, often appearing as leuco (colorless reduced) forms that can be oxidized to yield blue-violet dyes. Structurally, they differ from indamines by featuring para-amino substitutions on one aromatic ring, enhancing their reactivity in oxidative processes. In modern applications, indanilines are key components in oxidative hair dyeing formulations, where they form in situ through coupling reactions involving aromatic amines and phenols under alkaline peroxide conditions. Their solubility in aqueous media and tunable color shades make them suitable for semi-permanent coloring, though they share the class's general sensitivity to environmental factors. Both indamines and indanilines share roots in oxidative synthesis methods pioneered in the 19th century.^[50]^[52]

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[53]
Indamine - MFA Cameo - Museum of Fine Arts Boston
Aug 31, 2022 · A type of basic aniline compound whose salts form blue and green dyes. Indamine compounds were used as fabric dyes in the later 19th and early 20th century.Missing: historical | Show results with:historical
[54]
A review of developments in industrial hair colorant actives for ...
Aug 7, 2025 · In this technology, complex mixtures of indophenol, indaniline and/or indamine dyes are formed in situ within the hair fiber [23][24][25] [26] .