Introduction
C10H13N is a molecular formula that represents a family of organic compounds containing ten carbon atoms, thirteen hydrogen atoms, and one nitrogen atom. This stoichiometric arrangement is characteristic of a number of nitrogen‑containing molecules, including aromatic amines, aliphatic amines, and heterocyclic derivatives. Because the formula allows for a variety of structural arrangements, the designation C10H13N does not refer to a single compound but rather to a class of isomeric species that share the same elemental composition. The formula is frequently encountered in the context of synthetic organic chemistry, medicinal chemistry, and materials science, where subtle differences in molecular structure can lead to distinct physicochemical properties and biological activities.
In the chemical literature, C10H13N is often referenced as a target for synthesis or as a building block in the construction of more complex molecules. The diversity of possible isomers includes both primary and secondary amines, as well as tertiary amines when substituted with additional alkyl groups on the nitrogen. Aromatic amines, such as phenylalkylamines, feature prominently in pharmaceutical development, while aliphatic analogues are used in the manufacturing of plasticizers and surfactants. Because the nitrogen atom can be present in different hybridization states, compounds with this formula can exhibit a range of basicity and nucleophilicity, influencing their reactivity in organic transformations.
The following sections provide a detailed examination of the structural isomerism, synthetic routes, physical and chemical characteristics, applications, safety considerations, and related compounds associated with the molecular formula C10H13N. This comprehensive overview is intended to serve as a reference for researchers and practitioners working with nitrogen‑containing organic molecules that fall within this compositional window.
Structural Isomers
Arylalkylamines
One prominent subclass of C10H13N compounds is the arylalkylamines. These molecules feature a phenyl ring bonded to an aliphatic side chain that terminates in an amine functional group. A representative example is 1-phenyl-2-propylamine, which consists of a phenyl group attached to a propyl chain that ends with a primary amine. The placement of the nitrogen relative to the aromatic system influences the electron distribution and, consequently, the basicity of the amine. In arylalkylamines, the nitrogen is typically sp3‑hybridized and can engage in hydrogen bonding and ionic interactions in aqueous environments.
Another notable arylalkylamine is 2-phenyl-2-propylamine, where the nitrogen atom is positioned adjacent to the phenyl ring via a tertiary carbon center. This structural arrangement introduces steric hindrance around the nitrogen, affecting its accessibility to electrophiles. Such compounds are of interest in the design of ligands for metal coordination complexes and in the development of novel therapeutic agents that target specific receptors with high selectivity.
Alkylated Amines
Alkylated amines with the formula C10H13N are typically tertiary amines derived from the union of aniline derivatives and alkyl halides or via reductive amination of ketones or aldehydes. For instance, N,N-dimethyl-1-phenylpropan-1-amine is synthesized by treating 1-phenylpropan-1-amine with methyl iodide in the presence of a base, resulting in a tertiary amine that is fully substituted on the nitrogen. These molecules often exhibit increased lipophilicity compared to their primary counterparts, which can translate into improved membrane permeability in biological systems.
Secondary amines formed through the reaction of benzylamine with propyl bromide yield 1-phenyl-3-ethylamine, a structure that places the nitrogen one carbon away from the aromatic ring. This arrangement provides a balance between steric bulk and electronic influence, rendering such compounds suitable as intermediates in alkaloid synthesis and as scaffolds for the construction of heterocyclic systems.
Heterocyclic Derivatives
Heterocyclic compounds containing a nitrogen atom and fitting the C10H13N formula include bicyclic and tricyclic systems where the nitrogen is incorporated into a ring. A common example is 9,10-dihydro-9-phenyl-2,3,4,5-tetrahydro-1H-pyrrol-1-amine, a nitrogen‑containing bicyclic scaffold that can be derived from the cyclization of amino alcohols. The nitrogen within the ring often participates in conjugation with adjacent double bonds, which can modulate the compound’s reactivity toward electrophilic aromatic substitution or nucleophilic attack.
Other heterocyclic variants encompass piperidine derivatives, such as N-phenylpiperidin-2-amine, where the nitrogen is part of a six‑membered saturated ring. The presence of the nitrogen within the ring can influence the compound’s basicity, enabling it to act as a proton acceptor under physiological conditions. These structural motifs are frequently encountered in drug discovery projects focused on central nervous system activity.
Synthesis and Production
Laboratory Preparation
In a laboratory setting, C10H13N compounds are often synthesized through reductive amination, nucleophilic substitution, or coupling reactions. Reductive amination of phenylacetaldehyde with ammonia followed by catalytic hydrogenation yields 1-phenyl-2-propylamine in high yield. This method exploits the formation of an imine intermediate that is reduced by a hydrogen donor, typically palladium on carbon, under mild pressure conditions. The resulting primary amine can be isolated by standard extraction and purification techniques.
Nucleophilic substitution reactions employ alkyl halides reacting with aniline or phenylamine derivatives. For example, treating phenylamine with 1-bromopropane in the presence of potassium carbonate generates 1-phenyl-1-propylamine via an SN2 mechanism. The reaction proceeds efficiently at elevated temperatures, and the product can be purified by distillation or recrystallization. Subsequent alkylation steps, such as the addition of methyl groups, allow the preparation of tertiary amines with the same molecular formula.
Cyclization approaches are also used to assemble heterocyclic isomers. The condensation of 2,5-diamino-1,4-benzenedicarboxylic acid with a suitable alkyne, followed by a metal‑catalyzed cyclization, can produce tricyclic nitrogenous frameworks. These strategies often require carefully controlled reaction conditions to avoid over‑alkylation or side reactions that could compromise yield.
Industrial Processes
On an industrial scale, the synthesis of C10H13N compounds typically focuses on processes that maximize throughput while minimizing environmental impact. The manufacture of phenethylamine derivatives involves large‑scale reductive amination of commercially available aldehydes. Catalysts such as Raney nickel or supported ruthenium are employed to achieve high selectivity and low catalyst loading. Process conditions are optimized to limit the formation of by‑products and to enable downstream separation through crystallization or chromatography.
Industrial production of tertiary amines often utilizes alkylation steps that are conducted in aqueous media under basic conditions. The use of continuous flow reactors has become common, allowing precise control over residence time and reaction temperature, thereby enhancing product purity. Post‑reaction workup typically includes neutralization, solvent extraction, and distillation. Waste streams are treated through neutralization and biodegradation protocols to comply with environmental regulations.
Physical and Chemical Properties
General Properties
Compounds with the molecular formula C10H13N generally exhibit melting points ranging from 30 °C to 110 °C for solid derivatives and boiling points between 100 °C and 200 °C for liquids, depending on the degree of branching and the presence of aromatic rings. The presence of the nitrogen atom confers basicity, with pKa values for the conjugate acids typically between 9 and 11, indicating moderate proton affinity. Solubility in water varies with the specific isomer; primary and secondary amines tend to be more soluble due to hydrogen‑bonding capability, while tertiary amines are less water‑soluble but more soluble in organic solvents such as ethanol and dichloromethane.
Viscosity and refractive index data are also important for applications in materials science. For example, the refractive index of 1-phenyl-2-propylamine is approximately 1.50 at 20 °C, making it suitable for optical applications that require moderate refractive indices. The dielectric constant of these compounds generally lies between 4 and 7, reflecting their polar nature. These physical properties influence the choice of solvent and reaction conditions in synthetic procedures.
Spectroscopic Features
In proton nuclear magnetic resonance (¹H NMR) spectroscopy, the aromatic protons of arylalkylamines resonate between 7.0 and 7.5 ppm, while aliphatic methylene and methine protons appear between 1.2 and 3.5 ppm. The nitrogen‑attached methine proton often shows a chemical shift near 2.5 ppm with a characteristic multiplicity due to coupling with adjacent methylene groups. In ¹³C NMR spectra, the aromatic carbons resonate between 120 and 140 ppm, whereas the aliphatic carbons appear between 10 and 50 ppm. Carbon attached to nitrogen typically shows a shift around 50–60 ppm.
Mass spectrometry (MS) of C10H13N compounds yields a molecular ion at m/z 149, corresponding to the protonated molecule [M + H]⁺. Fragmentation patterns commonly display peaks at m/z 84 and 105, reflecting cleavage of the side chain or loss of the nitrogen substituent. Infrared (IR) spectroscopy shows a strong absorption band near 3300 cm⁻¹ due to N–H stretching, and a distinct absorption around 2950 cm⁻¹ attributable to C–H stretching of aliphatic chains. Aromatic C=C stretching appears near 1600 cm⁻¹, while N–C stretching manifests around 1150 cm⁻¹.
Applications
Pharmaceuticals
Several C10H13N isomers serve as intermediates in the synthesis of pharmaceutical agents. For instance, 1-phenyl-2-propylamine can be transformed into amide derivatives that act as antagonists for dopamine receptors. The presence of the amine functional group allows for the introduction of additional substituents that modulate pharmacokinetic properties. Similarly, tertiary amines derived from N,N‑dimethylation of arylalkylamines have been employed as basic building blocks for the synthesis of beta‑blockers and antihistamines, where the nitrogen plays a pivotal role in receptor binding.
In the development of central nervous system drugs, heterocyclic C10H13N compounds such as N‑phenylpiperidin‑2‑amine serve as scaffolds for the creation of selective monoamine oxidase inhibitors. The nitrogen within the ring structure enables the compound to interact with the enzyme’s active site through hydrogen bonding and electrostatic interactions. Additionally, these heterocyclic amines are utilized as precursors for the synthesis of novel psychoactive substances, underscoring the importance of strict regulatory controls over their production and distribution.
Agrochemicals
Certain aliphatic amines with the formula C10H13N are employed as intermediates in the production of insecticides and herbicides. The nitrogen atom facilitates the formation of salts that exhibit increased water solubility, which is advantageous for application in aqueous formulations. For example, 2-phenyl-2-propylamine derivatives are used as building blocks for the synthesis of organophosphorus insecticides, where the amine group is essential for the introduction of phosphate ester functionalities that inhibit acetylcholinesterase in target pests.
Materials Science
Solid C10H13N isomers are utilized in the manufacture of plasticizers that improve the flexibility of polymer matrices. Their moderate polarity and lipophilicity allow them to penetrate polymer chains, reducing intermolecular forces and increasing chain mobility. The amine group also acts as a reactive site for cross‑linking reactions with epoxide or anhydride monomers, thereby enhancing mechanical strength and thermal stability of the resulting polymers.
In electronic and optoelectronic applications, tertiary amines such as N,N‑dimethyl‑1‑phenylpropane‑1‑amine are incorporated into dielectric layers of organic field‑effect transistors. The nitrogen’s basicity improves charge transport properties by facilitating ionic gating. These materials find use in flexible displays and photovoltaic devices where organic semiconductors are required to maintain structural integrity under varying environmental conditions.
Safety and Environmental Considerations
Compounds containing C10H13N may present hazards such as skin irritation, respiratory irritation, and potential neurotoxicity. Primary and secondary amines can form irritant vapors, while tertiary amines may have lower acute toxicity but can still cause sensitization. Safety data sheets recommend the use of personal protective equipment, adequate ventilation, and adherence to handling protocols that prevent accidental inhalation or ingestion. In industrial settings, the implementation of closed‑system reactors and gas‑scrubbing units reduces the release of hazardous vapors into the atmosphere.
Biodegradation studies indicate that many C10H13N compounds are susceptible to microbial degradation under aerobic conditions, producing amides and carboxylic acids as final metabolites. However, certain isomers exhibit resistance to biodegradation due to steric hindrance around the nitrogen, necessitating advanced treatment processes such as catalytic oxidation or advanced oxidation processes for wastewater effluents. Compliance with environmental regulations, such as the European Union’s REACH directive, requires comprehensive risk assessments for each isomer before its widespread use.
Conclusion
Compounds with the molecular formula C10H13N encompass a diverse range of structures, including arylalkylamines, alkylated tertiary amines, and heterocyclic derivatives. Their synthesis is achieved through reductive amination, nucleophilic substitution, and cyclization techniques in laboratory and industrial contexts. The physical and spectroscopic properties of these molecules support a wide array of applications spanning pharmaceuticals, agrochemicals, and materials science. Owing to the potential for misuse, stringent safety protocols and regulatory oversight are essential to manage the production and distribution of C10H13N compounds.
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