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Benzamide

Benzamide is the simplest amide derivative of benzoic acid, consisting of a benzene ring attached to a carboxamide functional group (-CONH₂), with the molecular formula C₇H₇NO.^[1] It appears as a white to off-white crystalline powder that is sparingly soluble in water (approximately 1.35 g/100 mL at 20 °C) but more soluble in organic solvents such as ethanol and ether.^[2] Benzamide has a melting point of 125–128 °C and a boiling point of 288 °C, making it stable under standard laboratory conditions but combustible and incompatible with strong oxidizing agents.^[1] As a key intermediate in organic chemistry, benzamide is primarily synthesized by the reaction of benzoyl chloride with ammonia, often followed by recrystallization from hot water to purify the product.^[2] Alternative methods include the ammonolysis of benzonitrile using hydrogen peroxide and sodium hydroxide.^[3] It serves as a versatile starting material for the production of other compounds, such as benzonitrile through dehydration, and finds applications in the synthesis of pharmaceuticals, dyes, and agrochemicals.^[1] Substituted benzamides are notable in medicinal chemistry for their roles as analgesics, antipsychotics, and antiemetics, though the parent compound itself is mainly used in research and industrial processes.^[1] Safety considerations include its classification as harmful if swallowed (oral LD50 in mice: 1160 mg/kg) and a potential mutagen, requiring careful handling to avoid ingestion or inhalation.^[1]

Chemical Identity and Properties

Molecular Structure and Formula

Benzamide has the molecular formula C₇H₇NO, which can also be expressed in a structural form as C₆H₅CONH₂, highlighting the benzene ring bonded to the carboxamide moiety.^[1] Its molecular weight is 121.14 g/mol.^[1] This compound is an aromatic amide, characterized by a benzene ring directly attached to a carboxamide group (-CONH₂), positioning it as the simplest amide derivative of benzoic acid.^[1] The IUPAC name is benzamide, with the systematic designation benzenecarboxamide, and it is commonly known as phenylcarboxamide.^[1]^[4] For computational and database representation, its SMILES notation is c1ccc(cc1)C(=O)N.^[1]

Physical and Thermodynamic Properties

Benzamide appears as a white to off-white crystalline powder or colorless flakes, often forming monoclinic prisms or plates when crystallized from water. It is typically odorless, though some preparations may exhibit a faint aromatic scent.^[5] The compound has a melting point of 125–130 °C and a boiling point of 288–290 °C at standard atmospheric pressure. Its density is approximately 1.34 g/cm³ in the solid state at 20 °C. Benzamide exhibits moderate solubility in water, with a value of 13.5 g/L at 25 °C, and increased solubility in hot water. It is soluble in polar organic solvents such as ethanol, methanol, and acetone, as well as in benzene and ethyl ether (though to a lesser extent in the latter).^[6] The compound is insoluble in cold petroleum ether.^[7] Thermodynamically, the standard enthalpy of formation (ΔH_f°) for solid benzamide is -202.1 kJ/mol at 298 K.^[8] Its molar heat capacity (C_p) is 153.8 J/mol·K at 25 °C in the solid phase.^[8] These values reflect the stability and energy characteristics influenced by its aromatic amide structure, which enhances solubility in organic solvents relative to non-aromatic amides.

Synthesis

Laboratory Preparation

Benzamide is commonly prepared in the laboratory by the nucleophilic acyl substitution reaction of benzoyl chloride with ammonia, typically in an aqueous or ethereal medium. The reaction proceeds as follows:

\mathrm{C_6H_5COCl + NH_3 \rightarrow C_6H_5CONH_2 + HCl}

In a standard procedure, concentrated aqueous ammonia (specific gravity 0.880) is cooled in an ice bath, and benzoyl chloride is added dropwise with vigorous stirring to maintain the temperature between 0 and 25 °C and control the exothermic nature of the reaction. The mixture is shaken for 10–15 minutes until the odor of benzoyl chloride dissipates, then filtered to collect the precipitated benzamide, which is washed with cold water. Purification is achieved by recrystallization from hot water or dilute ethanol, yielding white crystals with up to 90% theoretical yield.^[9] An alternative laboratory method involves the partial hydrolysis of benzonitrile using hydrogen peroxide under basic conditions, which selectively hydrates the nitrile group to the amide without proceeding to the carboxylic acid. The reaction is:

\mathrm{C_6H_5CN + H_2O \rightarrow C_6H_5CONH_2}

Benzonitrile is mixed with 10% aqueous hydrogen peroxide and a catalytic amount of 10% sodium hydroxide solution, stirred at room temperature or mildly heated (25–35 °C) for several hours until completion, monitored by TLC or disappearance of nitrile IR absorption at ~2200 cm⁻¹. The product is extracted with an organic solvent, dried, and recrystallized from ethanol or water, affording benzamide in yields comparable to classical methods (70–90%). This approach is noted for its mild, green conditions avoiding harsh acids or bases.^[10]

Industrial Production

Benzamide is commercially produced on a large scale primarily through the partial hydrolysis of benzonitrile, often using sulfuric acid or other catalysts under controlled conditions to favor amide formation. This route leverages the availability of benzonitrile from industrial processes like the ammoxidation of toluene.^[11] An alternative method involves the reaction of benzoic acid with ammonia via an ester intermediate, such as methyl benzoate, in the presence of a cation exchanger catalyst. This process includes esterification followed by ammonolysis, offering high purity (99.6–99.8%) and environmental benefits through reusable reagents.^[11]

Chemical Reactions

Benzamide undergoes acid-catalyzed hydrolysis in the presence of hydronium ions, cleaving the amide bond to produce benzoic acid and the ammonium cation. \ce{C6H5CONH2 + H3O+ -> C6H5COOH + NH4+} This transformation is typically performed by boiling the amide in 6 M hydrochloric acid for 1–2 hours, affording benzoic acid in yields exceeding 95% after isolation and purification.^[12] The reaction proceeds via a mechanism involving protonation of the carbonyl oxygen, followed by nucleophilic attack by water and subsequent elimination of ammonia, consistent with the AAc2 pathway for amide hydrolysis.^[13] Under basic conditions, benzamide is hydrolyzed by hydroxide ions to the benzoate anion and ammonia gas. \ce{C6H5CONH2 + OH- -> C6H5COO- + NH3} Standard laboratory conditions involve refluxing benzamide (5 g) with 10% aqueous sodium hydroxide (75 mL) for 30 minutes, during which ammonia is evolved; the mixture is then cooled and acidified with concentrated hydrochloric acid to precipitate benzoic acid, which is collected, washed, and recrystallized from boiling water.^[14] This saponification-like process exploits the nucleophilic addition of hydroxide to the carbonyl, leading to tetrahedral intermediate collapse and expulsion of the amide nitrogen as ammonia.^[15] While full hydrolysis to carboxylic acid and amine derivatives predominates under forcing conditions, milder acidic or basic treatments can represent the reverse of partial hydrolysis pathways observed in nitrile-to-amide conversions, serving as a degradation route in synthetic contexts.^[16] The kinetics of benzamide hydrolysis are notably slower than those of analogous ester hydrolyses, attributable to resonance stabilization of the amide carbonyl by the nitrogen lone pair, which reduces electrophilicity and elevates the activation barrier to approximately 80–100 kJ/mol.^[17]

Dehydration and Other Reactions

Benzamide undergoes dehydration to form benzonitrile, a key transformation in organic synthesis, typically facilitated by strong dehydrating agents such as phosphorus pentoxide (P₄O₁₀). The reaction proceeds as follows:

\ce{C6H5CONH2 -> C6H5CN + H2O}

Heating benzamide with P₄O₁₀ in a microwave reactor for 1–2.5 minutes yields benzonitrile in up to 90%. Traditional heating methods require temperatures around 220–350 °C to achieve comparable efficiency, as lower temperatures result in slow reaction rates. Alternatively, thionyl chloride (SOCl₂) serves as a dehydrating agent, producing benzonitrile alongside gaseous byproducts like HCl and SO₂, though yields are generally lower (around 5–50% depending on conditions) and often require pressurized setups at 150–175 °C. This method is noted for its ease of handling but is less commonly used for benzamide due to side reactions.^[18]^[19]^[20]^[21] In the Hofmann rearrangement, benzamide is converted to aniline, shortening the carbon chain by one atom and serving as a vital route for primary amine synthesis from carboxylic acid derivatives. The process involves treatment with bromine and sodium hydroxide:

\ce{C6H5CONH2 + Br2 + 4 NaOH -> C6H5NH2 + Na2CO3 + 2 NaBr + 2 H2O}

The reaction initiates at low temperatures (0–5 °C) to form the N-bromoamide intermediate, followed by heating to promote migration and isocyanate formation, ultimately yielding aniline upon hydrolysis. Yields for benzamide typically range from 60–80%, with variations depending on the base and halogen source; for instance, trichloroisocyanuric acid as an oxidant provides intermediate yields while improving atom economy. This rearrangement is particularly valuable for preparing aromatic amines where direct amination is challenging.^[22]^[23] Benzamide, as a primary amide, reacts with nitrous acid (HNO₂) under acidic conditions to produce benzoic acid and evolve nitrogen gas, distinguishing it from amine reactions that form diazonium salts. The transformation involves nitrosation of the amide nitrogen, followed by decomposition:

\ce{C6H5CONH2 + HNO2 -> C6H5COOH + N2 + H2O}

This effervescence of N₂ is a diagnostic test for primary amides, occurring readily at room temperature in aqueous media generated from NaNO₂ and HCl. No diazotized products form, as the amide lacks the free amino group required for stable diazonium ions.^[24] Thermal decomposition of benzamide at elevated temperatures (>250 °C) leads to benzonitrile and water as primary products, mimicking dehydration but without added reagents. Pyrolysis studies show benzonitrile formation dominating above 350 °C, with high yields under vacuum or catalytic conditions.^[19]

Applications

Industrial Uses

Benzamide serves primarily as a chemical intermediate in the production of benzonitrile through dehydration processes.^[1] This transformation is employed in industrial organic synthesis, where benzonitrile acts as a key building block for manufacturing dyes, pharmaceuticals, and rubber additives.^[25] The resulting benzonitrile derivatives contribute to the synthesis of azo dyes and other pigments used in textile and coating applications.^[26] Benzamide also plays a role in the dye industry as an intermediate for nitrile-based compounds that form azo dyes and pigments.^[27] Its derivatives facilitate colorant production through further functionalization, supporting formulations in printing and surface coatings.^[28] In agricultural chemicals, benzamide serves as a starting material for substituted derivatives used as insecticides,^[29] fungicides such as zoxamide that target oomycete pathogens in crops,^[30] and herbicides such as propyzamide.^[31]

Pharmaceutical and Research Applications

Benzamide serves as a foundational pharmacophore in various pharmaceutical compounds, particularly substituted benzamides that exhibit antagonism at dopamine D2 receptors. Metoclopramide, used as an antiemetic, and sulpiride, employed as an antipsychotic for treating schizophrenia, both rely on the benzamide core structure, with N-substitution on the amide group enhancing their selectivity and potency against D2 receptors.^[32]^[33] In research, benzamide has historical significance as the first organic compound demonstrated to exhibit polymorphism, discovered by Friedrich Wöhler and Justus von Liebig in 1832 through crystallization experiments that revealed distinct crystal forms with different melting points.^[34] This seminal observation laid the groundwork for crystal engineering, influencing modern studies on polymorphic control in pharmaceutical formulations to optimize drug stability and bioavailability. Benzamide continues to function as a model compound for investigating crystallization dynamics and polymorphic transformations, including the formation of metastable forms like II and III, which are challenging to isolate from solution due to rapid interconversion.^[35] Additionally, benzamide and its N-alkyl derivatives are utilized as prototypes to assess amide bond thermal stability in polyamide systems, providing insights into degradation mechanisms under heat. Biochemically, benzamide derivatives act as inhibitors of histone deacetylases (HDACs), enzymes involved in epigenetic regulation, with applications in cancer research by promoting histone acetylation and gene expression changes.^[36] For instance, certain N-(2-aminophenyl)benzamide scaffolds selectively target class I HDACs, demonstrating submicromolar inhibitory activity and potential in antitumor therapies.^[37] Benzamide itself inhibits poly(ADP-ribose) polymerase (PARP), a critical DNA repair enzyme, and is employed in studies to probe cellular responses to genotoxic stress by competing with NAD+ for binding.^[38] As of 2025, research continues to explore novel benzamide derivatives as sigma-1 receptor agonists for central nervous system disorders and as TEAD modulators for cancer treatment.^[39]^[40]

Substituted Benzamides

Substituted benzamides are derivatives of benzamide where modifications occur either on the nitrogen atom or on the benzene ring, leading to altered physical, chemical, and biological properties compared to the parent compound. These substitutions enable diverse applications in organic synthesis, materials science, and pharmacology by tuning solubility, reactivity, and bioactivity.^[1] N-substituted benzamides, such as N-methylbenzamide (C₆H₅CONHCH₃), feature an alkyl group on the amide nitrogen, which influences hydrogen bonding and polarity. N-Methylbenzamide is an off-white crystalline solid with a melting point of 82 °C and low water solubility (<1 mg/mL), making it suitable as an intermediate in organic synthesis rather than a broad solvent.^[41] It is commonly synthesized by the reaction of benzoyl chloride with methylamine under Schotten-Baumann conditions, where aqueous sodium hydroxide neutralizes the HCl byproduct to drive amide formation.^[42] This method yields high-purity products and is adaptable for other N-alkyl derivatives via alkylation of benzamide with alkyl halides in the presence of base.^[43] Ring-substituted benzamides introduce functional groups on the aromatic ring, modifying electronic properties and reactivity. For instance, 4-nitrobenzamide bears an electron-withdrawing nitro group para to the amide, which enhances the amide's electrophilicity and facilitates nucleophilic attack, unlike the unsubstituted benzamide.^[44] This compound appears as a white powder with a high melting point (201–203 °C) and limited solubility (<0.1 mg/mL in water), and it reacts with strong reducing agents to produce flammable gases or with azo compounds to generate toxic gases.^[44] Such reactivity alterations make it valuable in dye synthesis and as a precursor for pharmaceuticals. Similarly, 3,5-dimethoxybenzamide incorporates methoxy groups at the meta positions, conferring electron-donating effects that support its role in biological applications; for example, the derivative N-(4-methoxyphenyl)-3,5-dimethoxybenzamide induces G2/M phase cell cycle arrest and apoptosis in cancer cells such as HeLa.^[45] Certain substituted benzamides exhibit significant pharmacological activity, exemplified by metoclopramide (4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-methoxybenzamide), a ring- and N-substituted derivative approved by the FDA in 1979 for treating gastroesophageal reflux disease by enhancing gastrointestinal motility.^[46] This compound combines methoxy and amino-chloro substitutions on the ring with a substituted ethylamine chain on nitrogen, improving its dopamine D2 receptor antagonism and prokinetic effects. For synthesizing such complex derivatives, the Schotten-Baumann reaction is particularly useful for N-acylation, reacting substituted benzoyl chlorides with amines like N-substituted ethylenediamines in basic aqueous media to form the amide bond selectively.^[47] Other notable pharmacological examples include amisulpride and sulpiride, which are N-substituted benzamides functioning as atypical antipsychotics by selective D2/D3 receptor blockade.^[48]

Polymorphic Forms

Benzamide exhibits four known polymorphic forms, marking it as the first organic compound recognized to display polymorphism. This discovery was made by Friedrich Wöhler and Justus von Liebig in 1832, who observed distinct crystalline modifications during crystallization experiments, laying the foundation for the study of solid-state polymorphism in molecular compounds.^[49] Subsequent research has confirmed the existence of forms I, II, III, and IV, each with unique structural and thermodynamic characteristics that influence their stability and behavior.^[49] Form IV, a highly disordered polymorph with 2D stacking faults, was discovered in 2020 through melt crystallization and studies under confinement at small length scales.^[50] Form I is the thermodynamically stable polymorph under ambient conditions, adopting an orthorhombic crystal structure with a melting point of 128 °C. It typically forms through slow evaporation of solvent solutions, such as ethanol or water, yielding well-defined prismatic or plate-like crystals that are the most commonly encountered.^[51] In contrast, form II is metastable and monoclinic, exhibiting a lower melting point range of 110–115 °C; it is obtained via rapid cooling of melts or highly supersaturated solutions, often resulting in needle-like or twisted morphologies due to internal stresses during growth.^[52] Form III represents a high-temperature polymorph with an approximate melting point of 130 °C, also orthorhombic but distinct in packing; it can be accessed through heating form I or via mechanochemical methods in the presence of impurities like nicotinamide, and it interconverts reversibly with form I upon thermal cycling.^[35] These polymorphic variations significantly impact the physical properties of benzamide, particularly solubility and dissolution rates, which differ between forms due to variations in lattice energy and surface characteristics. Form II, for instance, shows enhanced solubility compared to the stable form I, potentially accelerating dissolution.^[51] Such differences have prompted extensive study in pharmaceutical formulation, where polymorph selection can optimize bioavailability and control release profiles in drug delivery systems.^[35]

Safety and Toxicology

Health Hazards

Benzamide poses acute health risks primarily through ingestion and inhalation, classified as harmful if swallowed under GHS criteria (Acute Toxicity Category 4). The oral LD50 in mice is 1160 mg/kg, indicating moderate toxicity upon ingestion.^[1]^[53] It may cause irritation to the eyes and respiratory tract upon exposure; skin contact is not irritating but may cause mechanical discomfort from dust, potentially leading to redness, discomfort, or coughing.^[53]^[1] Symptoms of acute exposure include gastric pain, nausea, vomiting, and abdominal pain, particularly following ingestion.^[1] Chronic exposure to benzamide is concerning due to its suspected mutagenic potential, classified under GHS as Germ Cell Mutagenicity Category 2 (H341: Suspected of causing genetic defects). In vitro studies demonstrate that it induces sister chromatid exchanges in Chinese hamster ovary cells and L1210 cells, supporting this classification.^[1] Benzamide has no classification by the International Agency for Research on Cancer (IARC) as a carcinogen.^[53] The primary exposure routes in laboratory or industrial settings are inhalation of dust, which can irritate the respiratory tract and cause coughing, and ingestion via accidental swallowing. Dermal absorption is minimal, with no specific acute dermal toxicity classification, though direct skin contact may still cause irritation.^[1]^[53] In case of exposure, first aid measures include moving the affected person to fresh air and providing artificial respiration if breathing is difficult for inhalation incidents; washing skin thoroughly with soap and water for dermal contact; and rinsing eyes with water for ocular exposure. For ingestion, rinse the mouth, do not induce vomiting, and seek immediate medical attention, as symptoms like nausea and abdominal pain may require professional evaluation.^[53]^[1]

Environmental Considerations

Benzamide exhibits moderate biodegradability under aerobic conditions, with soil microbial communities capable of degrading 96% of the compound in clayey soils within 3 days and 98% in organic soils within 13 days.^[1] This rapid degradation suggests a relatively short environmental persistence in terrestrial environments, though half-life estimates vary by soil type and microbial activity.^[1] Ecotoxicity assessments indicate low to moderate impacts on aquatic organisms, with an LC50 of 661 mg/L (96 h) for fathead minnows.^[1] The compound's low potential for bioaccumulation is supported by its octanol-water partition coefficient (log Kow) of approximately 0.64, limiting its uptake and magnification in food chains.^[1] Benzamide is listed on the Toxic Substances Control Act (TSCA) inventory in the United States as an active chemical substance.^[1] In the European Union, it is registered under the REACH regulation, with no specific restrictions imposed by the Environmental Protection Agency (EPA) beyond general monitoring of amide-containing industrial wastes. Primary release sources include industrial effluents from organic synthesis processes, such as those in pharmaceutical and dye production, where wastewater treatment effectively mitigates environmental discharge through biodegradation and filtration methods.^[1] Combustion of benzamide-containing materials may produce nitrogen oxides, contributing to air pollution if not controlled.^[1]

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