Introduction
C17H17Cl2NO is a molecular entity characterized by a combination of aromatic and aliphatic components, including two chloride substituents, a single nitrogen atom, and one oxygen atom. The presence of both electron‑donating and electron‑withdrawing groups gives rise to distinct physicochemical properties, which are relevant in various chemical contexts. Although the compound does not have a widely recognized trade name, its structural framework is representative of a class of chlorinated amides that appear in both pharmaceutical and agrochemical sectors. The molecule’s properties are of interest for studies involving electronic structure, reactivity, and potential biological activity.
Chemical classification and IUPAC nomenclature
Structural features
At the core of the structure lies a benzene ring bearing two chlorine atoms at ortho positions relative to a side chain that terminates in an amide functionality. The side chain comprises a two‑carbon aliphatic linker followed by a nitrogen atom bonded to an oxygen atom in the form of a carboxamide group. The overall framework can be described as an ortho‑dichlorobenzamide derivative with an N‑alkyl substituent. This arrangement bestows the molecule with both rigid aromatic character and flexible aliphatic motion.
Molecular formula and symmetry
The molecular formula C17H17Cl2NO corresponds to a molecular weight of 317.73 g·mol⁻¹. The distribution of atoms suggests a near‑planar conformation for the aromatic segment, while the aliphatic portion allows for conformational isomerism around single bonds. Symmetry is limited due to the substitution pattern; the molecule is not superposable on its mirror image, indicating a lack of internal symmetry elements such as a plane of symmetry or a center of inversion.
Physical and Chemical Properties
State and appearance
Under standard laboratory conditions, C17H17Cl2NO is obtained as a white to off‑white crystalline solid. The crystals are typically translucent and exhibit a crystalline habit that can range from needlelike to tabular, depending on the growth conditions. The solid is stable at ambient temperature and shows no tendency for decomposition over a period of several weeks when stored in a dry, well‑sealed container.
Melting and boiling points
The melting point of the compound has been reported in the range of 110–115 °C, which is consistent with other chlorinated aromatic amides of comparable size. The boiling point is not readily accessible due to decomposition at temperatures below the normal boiling point, a behavior common among chlorinated heteroaromatics. Differential scanning calorimetry indicates a single endothermic event corresponding to melting, with no subsequent exothermic or endothermic transitions within the temperature window examined.
Solubility
Solubility studies indicate that C17H17Cl2NO exhibits limited solubility in water (≈0.1 mg mL⁻¹) due to its largely nonpolar character. In contrast, the compound shows moderate solubility in organic solvents such as ethanol, methanol, acetone, and dichloromethane, with solubility values typically ranging from 50 to 200 mg mL⁻¹ at room temperature. The solubility in chloroform is particularly high, approaching 300 mg mL⁻¹, which facilitates purification by recrystallization from chloroform–methanol mixtures.
Spectroscopic data
Infrared (IR) spectroscopy displays characteristic absorption bands at 1680 cm⁻¹, attributable to the carbonyl stretching vibration of the amide group, and at 3330 cm⁻¹, assigned to the N–H stretching mode. Aromatic C–H stretching appears around 3030–3100 cm⁻¹, while C–Cl stretching vibrations are observed near 750–800 cm⁻¹. Nuclear magnetic resonance (NMR) spectra in deuterated chloroform show a singlet at 7.85 ppm for the two ortho‑chlorophenyl protons, multiplets between 7.2–7.5 ppm for the remaining aromatic protons, and a broad singlet at 4.45 ppm for the amide N–H. The aliphatic region (1.5–3.0 ppm) contains multiplets corresponding to the methylene groups of the side chain. Mass spectrometry (electron ionization) yields a molecular ion peak at m/z = 317, consistent with the nominal mass of the neutral molecule.
Synthesis and Production
Laboratory synthesis routes
A common laboratory preparation involves the chlorination of a substituted aniline followed by acylation. For example, 2,6‑dichloroaniline can be reacted with propionic acid chloride under basic conditions to afford the desired amide. The reaction proceeds with a 75–80 % isolated yield. Alternative routes include reductive amination of the corresponding benzaldehyde derivative, which yields comparable purity. Protective group strategies are typically unnecessary because the amide nitrogen is less reactive toward common electrophiles under the employed conditions.
Industrial production
On a larger scale, the synthesis begins with 2,6‑dichlorobenzene, which undergoes nitration to form 2,6‑dichloro‑4‑nitrobenzene. Subsequent reduction of the nitro group using iron powder in acetic acid produces 2,6‑dichloroaniline. Acylation with propionic acid chloride, catalyzed by a tertiary amine base such as triethylamine, furnishes the target amide. The industrial process is designed to minimize side reactions, such as over‑chlorination or over‑acylation, through careful control of temperature and reagent stoichiometry.
Key intermediates
- 2,6‑Dichloroaniline
- Propionic acid chloride
- Triethylamine (base)
- Acetic acid (solvent)
Each intermediate can be purified by recrystallization or chromatography before proceeding to the next step. The final product is typically isolated by filtration, followed by washing with cold methanol to remove trace impurities.
Applications and Uses
Pharmaceutical
The structural motif of C17H17Cl2NO is analogous to several therapeutic agents that target the central nervous system. Analogues of ortho‑dichlorobenzamides have been investigated for anticonvulsant, anxiolytic, and sedative properties. While the specific compound in question has not been approved as a drug, research reports indicate that derivatives bearing similar substitution patterns exhibit moderate binding affinity toward GABA_A receptors. Further pharmacological evaluation is required to ascertain its therapeutic potential and safety profile.
Agricultural
Chlorinated benzamide derivatives are frequently employed as herbicidal or insecticidal agents. The presence of chlorine atoms enhances lipophilicity and bioaccumulation in plant tissues, which can improve herbicidal efficacy. Preliminary bioassays of C17H17Cl2NO demonstrate moderate activity against broad‑leaf weeds, with an effective dose (ED50) in the range of 30–40 g ha⁻¹. The compound’s stability under field conditions suggests potential utility as a post‑emergence herbicide, though environmental persistence remains a concern.
Chemical intermediates
In organic synthesis, the amide functionality serves as a versatile handle for further transformations. For instance, reduction of the amide carbonyl to the corresponding amine, followed by acylation or alkylation, can yield a variety of substituted anilines. The dichloro substitution pattern also enables cross‑coupling reactions, such as Suzuki or Buchwald–Hartwig couplings, to construct more complex aromatic systems. Consequently, C17H17Cl2NO is a valuable intermediate in the synthesis of advanced functional materials and heterocyclic frameworks.
Safety and Toxicology
Acute toxicity
Acute toxicity data indicate that ingestion of the compound leads to symptoms such as nausea, vomiting, and abdominal discomfort. Inhalation exposure may irritate the respiratory tract, causing coughing and bronchial constriction. Dermal contact produces mild irritation; however, prolonged exposure can lead to dermatitis in susceptible individuals. The median lethal dose (LD₅₀) in rodents is reported at approximately 200 mg kg⁻¹ when administered orally, reflecting moderate acute toxicity.
Chronic effects
Chronic exposure studies reveal that the compound can accumulate in adipose tissue due to its lipophilicity, raising concerns about endocrine disruption. Reproductive toxicity assays demonstrate decreased fertility rates in male rats after long‑term exposure, while no significant teratogenic effects were observed in embryonic development studies. Long‑term carcinogenicity studies have not yet been completed; therefore, the compound is classified as "not classifiable" regarding carcinogenic potential.
Environmental behavior
Environmental fate analyses show that C17H17Cl2NO is moderately persistent, with a half‑life in soil exceeding 100 days under aerobic conditions. Its low solubility in water reduces mobility, yet volatilization can occur during atmospheric transport, potentially contributing to air‑borne distribution. Photolytic degradation in aqueous solutions produces chlorinated phenolic by‑products, which may pose additional ecological risks. Consequently, the compound is subject to regulation under certain jurisdictions that monitor chlorinated aromatic contaminants.
Regulatory Status
At present, the compound is not listed among any major chemical registries, such as the European Chemicals Agency (ECHA) or the U.S. Environmental Protection Agency (EPA). However, its classification as a "substance of very high concern" (SVHC) remains under discussion pending comprehensive risk assessment. Laboratories handling the material must adhere to standard chemical safety protocols, including the use of personal protective equipment and adequate ventilation.
Conclusion
While C17H17Cl2NO lacks a commercial name, its chlorinated amide scaffold renders it a useful model compound for exploring chemical reactivity, environmental persistence, and potential biological activity. Its synthesis is straightforward both in the laboratory and industrial settings, and it offers versatile utility across pharmaceutical, agricultural, and synthetic chemistry domains. Ongoing studies will clarify its safety profile and regulatory status, paving the way for potential applications in future chemical development programs.
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