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O-Chloro-p-nitroaniline is typically encountered as a yellow to orange crystalline solid, which exhibits limited solubility in water but good solubility in polar organic solvents such as acetone, ethanol, or dimethylformamide, allowing it to be easily incorporated into chemical reactions or industrial processes while maintaining stability under normal handling conditions.
O-Chloro-p-nitroanilines electron-withdrawing nitro group enhances the stability of the diazonium intermediates, which makes it a preferred precursor in the manufacture of azo pigments, specialty dyes, and other functional aromatic compounds where precise color strength, chemical stability, and process reliability are required.
CAS Number: 89-63-4
Molecular Formula:C6H5ClN2O2
Molecular Weight:172.57
Synonyms: 2-Chloro-4-nitroaniline, 121-87-9, Ocpna, 2-Chloro-4-nitrobenzenamine, o-Chloro-p-nitroaniline, 4-Nitro-2-chloroaniline, 1-AMINO-2-CHLORO-4-NITROBENZENE, Benzenamine, 2-chloro-4-nitro-, Aniline, 2-chloro-4-nitro-, 2-chloro-4-nitrophenylamine, ortho-Chloro-para-nitroaniline, XSA3ZX337B, DTXSID4021973, NSC-3548, DTXCID201973, 204-502-2, RefChem:429187, 2-chloro-4-nitro-aniline, MFCD00007665, 2-Chloro-4-nitro-phenylamine, EN300-17939, CCRIS 2648, HSDB 5405, NSC 3548, EINECS 204-502-2, UNII-XSA3ZX337B, BRN 0638657, AI3-09084, 4-AMINO-3-CHLORONITROBENZENE, 2-chlor-4-nitroanilin, WLN: ZR BG DNW, 2-chloranyl-4-nitro-aniline, 4-12-00-01675 (Beilstein Handbook Reference), SCHEMBL532698, (2-chloro-4-nitrophenyl)amine, orb2893570, SCHEMBL7507577, CHEMBL1893710, SCHEMBL15630259, SCHEMBL31438898, 2-Chloro-4-nitroaniline, 99%, NSC3548, (2-chloro-4-nitro-phenyl)-amine, BDBM626062, CHLORO-4-NITROANILINE, 2-, Tox21_303921, SBB028370, SBB056667, STK358782, AKOS000120340, AC-7419, BS-3940, CS-W020588, NCGC00164027-01, NCGC00357167-01, CAS-121-87-9, ST010158, NS00010131, D88095, 1-AMINO-2-CHLORO-4-NITROBENZENE [HSDB], A804801, AE-562/40244765, Q2597946, Z57126995, F0001-0350, InChI=1/C6H5ClN2O2/c7-5-3-4(9(10)11)1-2-6(5)8/h1-3H,8H.
O-Chloro-p-nitroaniline is a synthetic aromatic amine compound characterized by a benzene ring substituted with a chloro group at the ortho position (position 2) and a nitro group at the para position (position 4) relative to the amino group, giving it the chemical formula C6H5ClN2O2; this specific arrangement of functional groups makes it both electron-withdrawing and reactive, which contributes to its use as a key intermediate in the synthesis of dyes, pigments, agrochemicals, and specialty organic compounds, as well as in research applications involving azo coupling reactions or aromatic substitution chemistry.
Chemically, o-Chloro-p-nitroaniline exhibits moderate polarity due to the nitro and amino substituents, and it has properties typical of substituted anilines, including the ability to participate in electrophilic aromatic substitution reactions, diazotization, and nucleophilic transformations, which make it a versatile building block in chemical manufacturing.
O-Chloro-p-nitroanilines solid crystalline form, yellow to orange color, and limited solubility in water but good solubility in polar organic solvents facilitate its handling in industrial and laboratory environments, where it is often used in controlled quantities to produce azo dyes, pigments like Pigment Red 170 derivatives, and other functionalized aromatic chemicals.
From a safety perspective, o-Chloro-p-nitroaniline is reactive and potentially hazardous if mishandled, as it can act as a skin, eye, and respiratory irritant, and its functional groups make it capable of producing toxic degradation products under strong chemical or thermal conditions, so handling it requires appropriate personal protective equipment, controlled laboratory or industrial conditions, and adherence to safety protocols.
O-Chloro-p-nitroaniline is aminated at 165 ℃ by using a process similar to that described for 2- nitroaniline.
O-Chloro-p-nitroaniline forms explosive products on reaction with nitric acid.
Can react with oxidizing agents.
O-Chloro-p-nitroaniline is a synthetic, substituted aromatic amine (2-Chloro-4-nitroaniline) with a benzene ring carrying chloro and nitro functional groups, used primarily as a chemical intermediate in the production of dyes, pigments, agrochemicals, and specialty organic compounds, valued for its reactivity, polarity, and suitability for aromatic substitution and azo coupling reactions, while requiring careful handling due to its irritant properties and potential chemical hazards.
Melting point: 117-119 °C (lit.)
Boiling point: 200 °C (rough estimate)
Density: 1.37
Refractive index: 1.6460 (estimate)
Flash point: 191 °C
Storage temp.: Room temperature
Solubility: 0.5 g/L (anhydrous substance)
pKa: pK1: 1.10 (+1) (25 °C)
Colour Index: 37040
Form: Crystalline powder or chunks
Color: Orange
pH: 7 (0.5 g/L, H2O, 20 °C)
Water Solubility: Insoluble
BRN: 512436
Stability: Stable. Combustible. Incompatible with strong oxidizing agents.
O-Chloro-p-nitroaniline is a synthetic aromatic amine compound in which a benzene ring is substituted with a chloro group at the ortho position (position 2) and a nitro group at the para position (position 4) relative to the amino group, giving it a highly specific molecular arrangement that results in distinct chemical reactivity, moderate polarity, and electron-withdrawing behavior due to the nitro and chloro substituents.
This combination of functional groups makes the compound particularly useful as a key intermediate in the synthesis of azo dyes, pigments, and specialty chemicals, as it can undergo diazotization reactions to form diazonium salts, electrophilic aromatic substitution, nucleophilic substitutions, and other transformations that are essential for producing high-performance colorants, chemical intermediates, and fine chemicals.
From an industrial and laboratory perspective, o-Chloro-p-nitroaniline is handled with care due to its potential hazards, as the combination of amino, chloro, and nitro groups can lead to irritation of the skin, eyes, and respiratory tract, and exposure to high temperatures, strong reducing agents, or reactive chemicals can result in decomposition products that may be toxic or hazardous, necessitating the use of personal protective equipment, fume hoods, proper ventilation, and strict adherence to safety protocols.
Despite these considerations, its reactivity and functional versatility make it an indispensable chemical in dye and pigment synthesis, organic chemical research, and specialty industrial applications, particularly when high-purity, structurally defined intermediates are required for consistent and high-quality end products.
O-Chloro-p-nitroaniline is a synthetic aromatic amine with a benzene ring substituted at the ortho and para positions with chloro and nitro groups, respectively, serving as a critical intermediate in the production of azo dyes, pigments, specialty chemicals, and functionalized aromatic compounds, valued for its reactivity, solubility in polar organic solvents, and stability for chemical transformations, while requiring careful handling due to its potential irritant and toxic properties under certain conditions.
Uses:
O-Chloro-p-nitroaniline is used almost exclusively as an intermediate in the synthesis of pigments.
The greatest potential for human exposure to 4-chloro-2- nitroaniline is in production and use of pigments made from the compound.
O-Chloro-p-nitroaniline is extensively used as a versatile intermediate in the chemical industry, where its amino group in combination with the chloro and nitro substituents on the aromatic ring enables a wide range of chemical transformations, including diazotization, azo coupling, nucleophilic substitution, and electrophilic aromatic reactions, which are essential for the production of high-performance azo dyes and pigments used in textiles, plastics, inks, paints, coatings, and specialty colorants, providing vivid red to orange shades, high opacity, and excellent lightfastness and chemical resistance, which are required for commercial, decorative, and industrial applications where long-term color stability is critical.
In the pharmaceutical and agrochemical industries, o-Chloro-p-nitroaniline functions as a building block for synthesizing active intermediates, where its electron-withdrawing nitro group and reactive amino functionality allow chemists to design and manufacture herbicides, fungicides, insecticides, and certain pharmacologically active compounds, ensuring precise chemical modification, controlled reactivity, and high product purity necessary for regulatory compliance and effective bioactivity.
O-Chloro-p-nitroaniline is primarily used as a key chemical intermediate in the synthesis of azo dyes and pigments, where its specific arrangement of chloro and nitro functional groups on the benzene ring allows for controlled diazotization reactions and coupling with other aromatic compounds, resulting in bright, durable, and colorfast dyes for applications in textiles, inks, plastics, coatings, and specialty colorants, where consistent hue, high lightfastness, and chemical stability are essential for both industrial and commercial products.
In addition to its role in the dye and pigment industry, o-Chloro-p-nitroaniline serves as a building block for agrochemicals, pharmaceuticals, and other specialty organic compounds, where its reactive amino group and electron-withdrawing chloro and nitro substituents allow chemists to perform electrophilic and nucleophilic substitutions, amide formations, and other functional modifications, enabling the production of herbicides, fungicides, and certain pharmacologically active intermediates that require high purity and well-defined chemical structure.
In laboratory and research settings, o-Chloro-p-nitroaniline is also used in organic synthesis studies, chemical education, and mechanistic research, where it functions as a model compound for studying aromatic substitution reactions, azo coupling reactions, and the effects of electron-withdrawing groups on reactivity, providing valuable insights into reaction mechanisms and synthetic strategies.
Furthermore, in specialty industrial processes, o-Chloro-p-nitroaniline can be employed in the manufacture of colorants for plastics, coatings, and printing inks, where it contributes to high opacity, uniform dispersibility, and resistance to fading under light, heat, and chemical exposure, which are critical properties for long-lasting, high-performance materials.
O-Chloro-p-nitroaniline is widely used as a chemical intermediate in the synthesis of azo dyes, pigments, agrochemicals, pharmaceuticals, and specialty organic compounds, valued for its reactivity, ability to undergo diazotization and coupling reactions, and compatibility with a wide range of chemical transformations, and it plays a crucial role in industrial colorants, high-performance coatings, plastics, inks, and research applications where consistent, durable, and high-quality chemical products are required.
O-Chloro-p-nitroaniline is also used in research laboratories and educational settings as a model substrate for studying aromatic substitution, diazonium chemistry, and the effects of electron-withdrawing groups on reactivity, where its well-defined structure and predictable behavior under controlled conditions make it a valuable tool for chemical mechanism investigations, synthetic method development, and demonstration experiments in advanced organic chemistry.
Additionally, in specialty materials and polymer industries, o-Chloro-p-nitroaniline is incorporated into high-performance dyes and colorants for engineering plastics, automotive coatings, decorative laminates, and industrial inks, where it contributes to consistent dispersion, enhanced color intensity, and resistance to thermal or chemical degradation, which are critical for end products exposed to heat, light, or solvents during manufacturing or end use.
Safety Profile:
O-Chloro-p-nitroaniline is considered a moderately toxic aromatic amine, and exposure to this compound through inhalation, ingestion, or dermal contact can cause adverse health effects, as it may be absorbed through the skin or respiratory tract and exert systemic toxicity, particularly affecting the blood, liver, and kidneys when handled in significant amounts or over prolonged periods.
Direct contact with o-Chloro-p-nitroaniline can result in skin irritation, redness, or dermatitis, especially in sensitive individuals or in cases of repeated exposure, while accidental eye contact can lead to mechanical irritation, redness, tearing, and discomfort, making the use of protective gloves, goggles, and clothing essential in both laboratory and industrial settings.
Inhalation of dust, powder, or vapors of o-Chloro-p-nitroaniline may cause respiratory tract irritation, coughing, sneezing, or shortness of breath, and prolonged or high-level exposure in poorly ventilated areas can increase the risk of pulmonary irritation or systemic toxic effects, highlighting the importance of fume hoods, proper ventilation, and respiratory protection during handling.
