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Indane

Indane, also known as indan, is a bicyclic organic compound with the molecular formula C₉H₁₀ and a molecular weight of 118.18 g/mol.^[1]^[2] It features a benzene ring fused to a five-membered cyclopentane ring, forming an ortho-fused bicyclic hydrocarbon structure.^[3]^[2] As a petrochemical, indane is a colorless to faintly yellow liquid that is insoluble in water but soluble in organic solvents such as alcohol and ether.^[2] Key physical properties include a boiling point of 176 °C, a melting point of -51 °C, a density of 0.965 g/mL at 25 °C, a flash point of 50 °C, and a refractive index of 1.537 at 20 °C.^[2] Thermodynamic data indicate an enthalpy of vaporization of approximately 49.2 kJ/mol and an enthalpy of fusion of 8.598 kJ/mol at its triple point of 221.77 K.^[1] Indane is flammable and poses aspiration hazards, requiring careful handling due to its irritant effects on skin and eyes.^[2] Indane occurs naturally in crude oil, where derivatives like methylindanes and dimethylindanes are present, and it serves as a core structural unit in various natural products.^[3] It is produced industrially through the isomerization of 3-phenyl-1-propene using AlCl₃ or by rectification from heavy benzene fractions.^[2] Applications include its role as a catalytic agent, an intermediate in organic synthesis for pharmaceuticals and biologically active compounds targeting infectious diseases and metabolic disorders, and an anti-vibration additive in aviation fuels and rubber.^[2]^[3]

Nomenclature and Structure

Molecular Formula and Structure

Indane possesses the molecular formula C₉H₁₀.^[4] Its molar mass is 118.176 g/mol.^[5] The molecule exhibits an ortho-fused bicyclic architecture, where a benzene ring shares two adjacent carbon atoms with a five-membered cyclopentane ring, resulting in a rigid, planar aromatic system integrated with an aliphatic cycle.^[4] In this fusion, a benzene ring shares two adjacent carbon atoms with a five-membered cyclopentane ring, forming a bicyclic hydrocarbon with nine carbon atoms in total.^[3] The canonical SMILES notation for indane is C1CC2=CC=CC=C2C1, illustrating the sequential connectivity: a three-carbon chain (C1-C-C1) closing the cyclopentane fused to the benzene (C2=CC=CC=C2).^[4] Indane serves as the saturated analog of indene (C₉H₈), differing by the addition of two hydrogen atoms that fully saturate the five-membered ring, eliminating the endocyclic double bond present in indene between positions 1 and 2. This saturation imparts greater stability to the aliphatic portion while preserving the aromatic character of the benzene ring.^[3]

Naming Conventions

Indane is known by its preferred IUPAC name, indane, which is a retained name for the ortho-fused bicyclic hydrocarbon systematically described as 2,3-dihydro-1H-indene.^[6] This retained status allows indane to serve as the parent structure in nomenclature for derivatives, reflecting its established use in chemical literature for the benzene ring fused to a saturated cyclopentane ring.^[6] Common alternative names include indan (a contracted form), benzocyclopentane (emphasizing the structural fusion of benzene and cyclopentane), and hydrindene (an older designation highlighting its relation to indene).^[7]^[8] The etymology of indane traces to indene, the unsaturated precursor, with the "-ane" suffix denoting the hydrogenation that saturates the five-membered ring.^[8] Indene, in turn, derives from "indole" (a related heterocyclic compound) combined with the "-ene" ending to indicate the carbon-carbon double bond.^[9] In IUPAC nomenclature for fused polycyclic systems, the naming of indane builds on the retained parent name indene, where the fusion is designated as for ortho-fusion between the benzene and five-membered rings; the "2,3-dihydro" prefix specifies the positions of saturation in the indene numbering system, with locants assigned to prioritize the fused bond and heteroatom absence.^[6]^[10]

Physical Properties

Appearance and Phase Behavior

Indane is a colorless to pale yellow liquid at room temperature and standard pressure.^[4]^[2] This appearance is characteristic of its pure form, with no significant coloration under typical laboratory conditions.^[11] The compound exhibits a melting point of -51 °C and a boiling point of 176 °C, confirming its stable liquid phase between these temperatures.^[2]^[12] At ambient conditions (around 25 °C), indane remains fully liquid, with no tendency to solidify or vaporize.^[4] Regarding solubility, indane is insoluble in water but readily dissolves in organic solvents, including ethanol, diethyl ether, and chloroform.^[2]^[12] This hydrophobic nature aligns with its nonpolar hydrocarbon structure, facilitating its use in non-aqueous environments.

Thermodynamic Properties

Indane has a density of 0.9645 g/cm³ at 20 °C.^[13] Its refractive index is 1.539 at 20 °C.^[14] The standard enthalpy of formation (ΔH_f°) for liquid indane is +2.56 ± 0.47 kcal/mol at 298.15 K, derived from calorimetric measurements.^[15] The corresponding standard enthalpy of combustion (ΔH_c°) is -1190.63 ± 0.47 kcal/mol, reflecting the energy released upon complete oxidation to CO₂ and H₂O.^[15] Heat capacity data for liquid indane at 298.15 K is 45.47 cal/mol·K, increasing to 47.79 cal/mol·K at 320 K, as measured in low-temperature calorimetry.^[15] Infrared spectroscopy of indane reveals characteristic C-H stretching absorptions: aromatic C-H at 3000–3100 cm⁻¹ and aliphatic C-H at 2850–2960 cm⁻¹, consistent with its fused ring structure.^[16] For ¹H NMR, the aromatic protons on the benzene ring resonate between 7.1 and 7.3 ppm, while the benzylic methylene protons on the cyclopentane ring appear at approximately 2.0–2.2 ppm, and the remaining aliphatic protons at 1.8–2.0 ppm, in CDCl₃ solvent.^[17]

Chemical Properties

Stability and Reactivity

Indane exhibits high thermal stability under ambient conditions, remaining intact up to its boiling point of approximately 176°C. Beyond this temperature, thermal decomposition occurs, yielding typical pyrolysis products associated with hydrocarbon breakdown.^[4]^[18] In terms of oxidation resistance, indane is relatively stable when exposed to air at room temperature, showing no significant reactivity under standard atmospheric conditions. However, it becomes susceptible to oxidation in the presence of strong oxidizing agents or under forcing conditions, such as elevated temperatures or catalytic environments, which can lead to partial or complete breakdown of the hydrocarbon structure.^[19]^[18] Indane is inherently non-acidic, with a pKa value exceeding 14, consistent with its nature as a saturated and aromatic hydrocarbon lacking functional groups capable of proton donation. It displays negligible basicity, attributable to the weak interaction potential of its aromatic π-electron system with electrophiles, rendering it practically neutral in acid-base contexts.^[20] The general reactivity profile of indane is governed by its bicyclic structure: the fused benzene ring facilitates electrophilic aromatic substitution, as demonstrated by direct chlorination reactions under standard EAS conditions. Conversely, the saturated five-membered aliphatic ring is prone to radical-mediated processes, including free-radical halogenation at the methylene positions, highlighting its vulnerability to homolytic cleavage pathways.^[21]

Key Reactions

Indane, with its fused benzene-cyclopentane structure, undergoes electrophilic aromatic substitution (EAS) primarily on the aromatic ring, directed by the alkyl substituent effect of the fused cyclopentane moiety toward positions 5 and 6. Nitration of indane using nitric acid in acetic anhydride proceeds via an electrophilic mechanism, yielding nitroindanes predominantly at the 5-position due to steric and electronic factors favoring para-like substitution relative to the fusion site, with relative reactivities at positions 4 and 5 reported as approximately 1.4:2.8.^[22] Halogenation, such as bromination, also occurs selectively at position 6 under controlled conditions, as demonstrated in substituted indanes where the directing group reinforces ortho-para orientation, though unsubstituted indane shows mixed 5- and 6-substitution products.^[23] Dehydrogenation of indane represents a key transformation to indene, involving the removal of two hydrogen atoms from the cyclopentane ring to form the unsaturated five-membered ring fused to benzene. This reaction is typically achieved through catalytic dehydrogenation in the vapor phase using a cobalt-molybdenum oxide catalyst supported on alumina, often in the presence of sulfur to enhance selectivity and suppress side reactions like cracking.^[24] The mechanism proceeds via stepwise hydrogen abstraction, stabilized by the aromatic system, yielding indene in high purity suitable for industrial applications.^[25] Radical reactions of indane target the benzylic positions on the cyclopentane ring, enabling alkylation due to the stability of the resulting radicals adjacent to the aromatic ring. Free radical-mediated alkylation, initiated by peroxides or light, allows introduction of alkyl groups at the 1- or 2-positions of the cyclopentane, with the process often involving hydrogen abstraction followed by coupling with alkyl radicals, as seen in polymer chain transfer mechanisms where indane acts as a model for intramolecular radical alkylation.^[3] A representative example of EAS on indane is Friedel-Crafts acylation with propionyl chloride in the presence of a Lewis acid catalyst like aluminum chloride, which preferentially acylates at the 5-position to form 5-propionylindane. This regioselectivity arises from the electron-donating effect of the fused ring directing the acylium ion to the para-equivalent site, producing the ketone in good yield without rearrangement due to the deactivating nature of the acyl group preventing polyacylation.^[26]

Synthesis and Production

Natural Occurrence

Indane is present in coal tar, a natural byproduct derived from the destructive distillation of coal, at low concentrations typically around 0.1-0.2%. For instance, gas chromatography analysis of coal tar from a coke production process revealed an indane content of 0.17%.^[27] The compound also occurs in petroleum fractions and natural hydrocarbon deposits, forming part of the aromatic components in crude oils. In Safaniya crude oil, indane contributes to the naphthenoaromatic fraction identified through detailed compositional studies.^[28] Indanes are recognized as naturally occurring hydrocarbons in various crude oil types, influencing the overall chemical profile of petroleum.^[3] Trace levels of indane and its derivatives appear in certain geological samples, such as the bitumen extracted from the Green River Shale. Here, alkyl-substituted hexahydroindane compounds, structurally related to indane, have been detected via mass spectrometry, potentially arising from the photochemical alteration of steroidal plant debris like the indane moiety in vitamin D.^[29] Indane derivatives are found in trace amounts in some plant-derived materials. For example, novel indane compounds (anisotindans A–D) were isolated from the roots of Anisodus tanguticus, a medicinal plant in the Solanaceae family, through chromatographic separation and spectroscopic analysis.^[30] Similar indane-based natural products have been reported in the rhizomes of Kniphofia reflexa.^[31]

Synthetic Methods

Indane is primarily produced industrially by the catalytic hydrogenation of indene, which saturates the double bond in the five-membered ring. This process uses supported noble metal catalysts, such as palladium or rhodium on activated carbon or alumina. The reaction proceeds selectively to indane under moderate to high pressure, with palladium catalysts particularly noted for halting at the indane stage without significant over-hydrogenation to hydrindane isomers.^[32] Typical conditions involve temperatures around 250 °C and hydrogen pressures of 50 bar, achieving full conversion of indene to indane within 1 hour and yields exceeding 90%.^[32] Indane can also be obtained industrially by rectification (distillation) from heavy benzene fractions or coal tar, where it is present at low levels (around 0.1-0.2%), yielding high-purity indane after fractionation. Alternative routes include acid-catalyzed isomerization of allylbenzene (3-phenyl-1-propene) using AlCl₃.^[2] Alternative laboratory routes include the intramolecular cyclization of phenylpropyl halides via palladium-catalyzed C–H alkylation. This method involves unactivated alkyl halides tethered to an aryl ring, proceeding under mild conditions with high functional group tolerance and yields often above 80%.^[33] Another established approach is the reduction of indanone, typically via Clemmensen reduction using zinc amalgam in concentrated hydrochloric acid. This deoxygenates the carbonyl group to a methylene, affording indane in good yields suitable for small-scale preparations, though the acidic conditions limit its use with acid-sensitive substrates.^[34]

Applications and Derivatives

Industrial Applications

Indane serves primarily as a chemical intermediate in organic synthesis within the petrochemical industry, where its bicyclic structure facilitates the construction of more complex hydrocarbons and aromatic compounds. It is employed in the production of specialty chemicals, leveraging its stability and reactivity for further functionalization.^[2] Additionally, indane acts as a petrochemical additive and catalytic agent in various synthetic processes, contributing to enhanced reaction efficiency.^[35] In polymer production, indane is incorporated as a building block to form high-performance materials, particularly through cationic polymerization methods that yield polymers with indane units. These polymers exhibit exceptional thermal stability in air and high glass transition temperatures ranging from 200°C to 250°C, making them suitable for demanding applications in specialty resins.^[36] Due to its hydrocarbon nature, indane is reported as an anti-vibration additive in aviation fuels, potentially improving damping properties. It is also utilized as an anti-vibration agent in the rubber industry, enhancing the damping properties of rubber formulations.^[2] Production of indane occurs on a minor industrial scale, mainly derived from coal tar processing via hydrogenation of indene, reflecting its limited natural abundance in coal tar fractions at approximately 0.1%.^[2]^[13]

Pharmaceutical and Chemical Derivatives

Indane serves as a core scaffold for various pharmaceutical derivatives, particularly in the development of psychoactive compounds. Among these, empathogen-entactogen derivatives such as 5,6-methylenedioxy-2-aminoindane (MDAI) and 5,6-methylenedioxy-N-methyl-2-aminoindane (MDMAI) have been synthesized as analogs of 3,4-methylenedioxymethamphetamine (MDMA), exhibiting entactogenic effects through selective serotonin release.^[37] MDAI, first prepared in the laboratory as a potential non-neurotoxic alternative to MDMA, features a methylenedioxy group at the 5,6-positions of the indane ring and an amino group at the 2-position, promoting empathy and euphoria in preclinical models.^[38] Similarly, MDMAI incorporates an N-methyl substitution on the amino group, enhancing its structural similarity to MDMA while maintaining the indane framework for rigidity.^[39] Amphetamine analogs derived from indane include 2-aminoindane (2-AI), a conformationally rigid cyclic variant of amphetamine that acts primarily as a central nervous system stimulant by interacting with monoamine transporters. 2-AI demonstrates selectivity for norepinephrine and dopamine transporters, with minimal activity at serotonin sites, making it a prototype for further modifications in stimulant research.^[40] Chemical derivatives of indane often involve alkylation to modify solubility and reactivity, such as 1-methylindane and 4-methylindane, which serve as intermediates in organic synthesis and pharmaceutical production. 1-Methylindane, with a methyl group at the 1-position of the fused ring, has been utilized in the synthesis of metabolites related to drugs like thalidomide and as a building block for more complex heterocycles.^[41] 4-Methylindane, featuring substitution on the benzene ring, contributes to fine-tuning steric properties in derivative libraries. Dimethylindanes, including 1,1-dimethylindane variants, are employed in perfumery and as synthons for substituted indanones with potential applications in fragrance chemistry.^[42] Synthesis of these pharmaceutical derivatives typically involves amination or substitution on the indane scaffold. For instance, 2-aminoindane derivatives like MDAI are prepared by initial cyclization of substituted 3-phenylpropionic acids to the corresponding indanones, followed by oxime formation and reduction (e.g., using lithium aluminum hydride or catalytic methods) to install the amine group.^[40] A [1,4]-hydride shift-mediated C(sp³)–H functionalization enables efficient construction of 1-aminoindane derivatives from alkylated indanes, achieving high yields with sterically hindered amines.^[43] These methods allow precise substitution at the 2-position for psychoactive compounds, leveraging the indane core's stability. Indane-based aminoindanes, including MDAI and related structures, have been extensively researched as selective serotonin-releasing agents, offering insights into entactogenic mechanisms without the neurotoxicity associated with phenethylamine analogs.^[37]

Safety and Environmental Considerations

Toxicity and Health Effects

Indane demonstrates low acute oral toxicity, with an LD₅₀ value of 3163 mg/kg in rats.^[18] Dermal exposure also shows low toxicity, with an LD₅₀ exceeding 2000 mg/kg in rabbits.^[18] These values indicate that indane is not highly toxic via ingestion or skin absorption under typical exposure scenarios, though ingestion poses an aspiration hazard, potentially leading to severe lung damage if the substance enters the airways. Inhalation of indane vapors at high concentrations can irritate the respiratory tract, causing discomfort or inflammation, though it is not expected to produce severe adverse effects at low levels.^[44] Direct skin contact may result in mild irritation or defatting, leading to non-allergic contact dermatitis upon prolonged exposure.^[18] Eye contact is similarly mild, potentially causing transient redness or tearing, but without classification as a serious irritant.^[18] Data on chronic effects, including carcinogenicity, are limited, with no evidence classifying indane as a carcinogen.^[18] Indane, as a component in mixtures, is subject to REACH via UVCB registrations (e.g., coal tar light oils), classified for aspiration toxicity (Category 1) with no additional specific health hazard classifications noted for the pure substance in available data.^[45]

Environmental Impact

Indane enters the environment mainly through industrial processes involving coal tar distillation, where it is a constituent of light oil fractions, and from incomplete combustion of fossil fuels and biomass. These sources contribute to its presence in air emissions, soil, and water bodies near processing facilities or combustion sites.^[45]^[4] Due to its fused aromatic-aliphatic structure, indane exhibits moderate persistence in soil and aquatic environments, resisting rapid biodegradation under aerobic conditions but showing slower degradation in mixed hydrocarbon systems. Studies indicate that indane can inhibit the microbial breakdown of co-occurring compounds like BTEX hydrocarbons, prolonging its environmental residence time.^[46] Indane's bioaccumulation potential is moderate, with an experimental octanol-water partition coefficient (log Kow) of 3.33, suggesting uptake in aquatic organisms but with a bioconcentration factor (BCF) estimated below 2000, not exceeding high bioaccumulation concern thresholds.^[47] Indane is classified as toxic to aquatic life with long-lasting effects (H411) under GHS.^[18] Indane, a hydroaromatic compound related to PAHs, may be monitored in hydrocarbon mixtures from coal tar and combustion sources in assessments of sediment and water quality, though not specifically under PAH criteria.^[48] Mitigation strategies for indane releases are constrained by its relatively low global production volumes, estimated in the niche chemical market segment rather than large-scale commodity production, limiting the scope for widespread remediation technologies. Efforts primarily involve source control in coal tar handling and combustion efficiency improvements.^[49]

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