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4‑Aminobenzonitrile is an organic compound with the molecular formula C₇H₆N₂. It occurs as white to light‑yellow crystals or powder. This stable organic solid has a relatively high melting point and density. It is slightly soluble in water, yet miscible with common organic solvents including ethanol, acetone and dimethylformamide. For researchers and manufacturers working on these fields, consistent‑quality starting materials are essential, and Bloomtechz provides reliable 4‑Aminobenzonitrile to support fine‑chemical, agro‑chemical and material‑related development work.
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Chemical Formula |
C7H6N2 |
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Exact Mass |
118 |
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Molecular Weight |
118 |
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m/z |
118 (100.0%), 119 (7.6%) |
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Elemental Analysis |
C, 71.17; H, 5.12; N, 23.71 |
In the field of chemistry, numerous compounds play critical roles in different industries due to their unique structures and properties. 4-aminobenzonitrile, as an important organic compound, has a unique chemical structure with both amino and cyano functional groups attached to its benzene ring. This unique structure endows it with rich chemical properties and a wide range of uses.
The use of 4-aminobenzonitrile in the pharmaceutical field
Drug Intermediates
4-aminobenzonitrile is a vital aromatic pharmaceutical intermediate bearing reactive amino and cyano groups on the benzene ring. Benefiting from its stable molecular skeleton and excellent chemical reactivity under mild reaction conditions, this compound serves as a versatile building block in the synthesis, structural modification and analytical detection of various clinical drugs. It has therefore become a fundamental material in modern pharmaceutical research and industrial-scale drug production.
As a key starting material for antibacterial drug synthesis,
4-aminobenzonitrile can construct novel heterocyclic molecular skeletons through controllable condensation, cyclization and coupling reactions. Unlike traditional antibiotics that easily induce bacterial resistance,the resulting antibacterial compounds possess unique action mechanisms by interfering with bacterial nucleic acid replication and protein synthesis. They exhibit prominent inhibitory effects on common drug-resistant strains such as methicillin-resistant Staphylococcus aureus and drug-resistant Gram-negative bacteria, effectively alleviating the growing clinical problem of antibiotic resistance.In anti-tumor drug development, 4-aminobenzonitrile acts as a critical structural precursor for targeted therapeutic molecules.
Incorporating its rigid aromatic skeleton into anti-tumor agents significantly optimizes drug target specificity, enabling precise binding to specific receptors and signaling pathways on tumor cell surfaces.Meanwhile, they greatly reduce unnecessary damage to normal human cells, lowering systemic toxic and side effects and improving the safety and efficacy of clinical targeted anti-tumor therapy.
Functional Group Conversion in Drug Synthesis
The coexistence of amino and cyano functional groups endows 4-aminobenzonitrile with diverse and controllable transformation pathways,supporting flexible structural optimization of drug molecules.
These efficient modification reactions can precisely adjust the physicochemical properties and in vivo metabolic behaviors of candidate drugs,providing reliable technical support for the development of high-efficiency, low-toxicity and clinically safer new pharmaceutical products.Acylation modulates drug lipid solubility and cell membrane permeability to enhance oral bioavailability, while sulfonation improves water solubility and optimizes in vivo absorption and distribution. Amino derivatization also enriches drug molecular structures and optimizes ADME properties.The cyano group can be hydrolyzed into carboxyl groups to synthesize carboxylic acid drugs with enhanced polarity and bioactivity,or reduced into amino groups to increase molecular active sites and improve drug-target binding affinity.
Application in Drug Analysis
Beyond synthetic applications, 4-aminobenzonitrile serves as a high-efficiency derivatization reagent in modern pharmaceutical analysis.Its nucleophilic amino group and conjugated benzene ring structure allow it to efficiently react with carboxyl, hydroxyl and carbonyl groups in drug molecules under mild conditions, generating stable derivatives with superior spectral sensitivity and chromatographic separation performance.It solves the defects of weak spectral response and poor separation of trace drugs in HPLC and GC detection.Derivatization significantly amplifies drug signal response and improves chromatographic peak symmetry, realizing sensitive qualitative and quantitative analysis of trace pharmaceutical components.
The obtained derivatives can effectively avoid matrix interference from complex biological samples and pharmaceutical excipients. This derivatization technology is widely applied in drug purity testing, trace residue detection, pharmaceutical quality control and pharmacokinetic research.It significantly improves the accuracy, sensitivity and reproducibility of drug qualitative and quantitative analysis, providing strong technical guarantees for standardized drug production and reliable clinical medication safety.
The use of 4-aminobenzonitrile in the field of dyes and pigments
Synthetic dyes
4-aminobenzonitrile is an important raw material for the synthesis of various dyes. When synthesizing azo dyes, it can participate in the reaction as a diazo component or coupling component. Azo dyes with bright colors and good dyeing properties can be generated through diazotization and coupling reactions with aromatic amines or phenolic compounds. These azo dyes are widely used in dyeing processes in industries such as textiles, leather, and papermaking, and can endow various materials with rich and diverse colors.
4-aminobenzonitrile can also play an important role in the synthesis of anthraquinone dyes. It can participate in the construction of anthraquinone rings and functional group modification reactions, synthesizing anthraquinone dyes with different structures and properties. Anthraquinone dyes have the advantages of bright color, good wash fastness, and high light fastness, and are commonly used for dyeing and printing high-end textiles.
Synthetic pigments
In addition to dyes, 4-aminobenzonitrile can also be used for synthesizing pigments. When synthesizing organic pigments, it can serve as a key intermediate in the molecular structure design of pigments. By reacting with other organic compounds, pigment molecules with specific conjugated systems and spatial structures are constructed, which have high coloring and covering power and can meet the requirements of different fields for pigment performance. For example, some organic pigments synthesized from 4-aminobenzonitrile are widely used in coloring industries such as paints, inks, plastics, etc., providing good appearance and decorative effects for products.
Improving the Performance of Dyes and Pigments
The introduction of 4-aminobenzonitrile can also improve the performance of dyes and pigments. Introducing 4-aminobenzonitrile structural units into dye molecules can adjust the molecular polarity and intermolecular forces of the dye, thereby affecting the adsorption and diffusion properties of the dye on fibers, and improving the dye uptake and color fastness. For pigments, the addition of 4-aminobenzonitrile can improve the dispersibility and stability of the pigment, enabling better dispersion in the medium, reducing agglomeration, and improving the effectiveness and product quality of the pigment.
The use of 4-aminobenzonitrile in the field of pesticides
Synthesis of pesticide intermediates
4-aminobenzonitrile is an important intermediate for the synthesis of various pesticides. In the synthesis of insecticides, it can participate in the construction of molecular structures with insecticidal activity. For example, by reacting with specific heterocyclic compounds or halogenated hydrocarbons, new intermediate compounds of pyrethroid insecticides can be synthesized. These intermediates are further synthesized to obtain insecticides with high efficiency, low toxicity, and broad spectrum, which have good control effects on agricultural and sanitary pests.4-Aminobenzonitrile can also be used as a key raw material in the synthesis of fungicides.
It can react with some nitrogen-containing and sulfur-containing compounds to generate heterocyclic compounds with bactericidal activity.These fungicides can inhibit the growth and reproduction of pathogens, protecting crops from disease invasion.
Modification of pesticide active ingredients
By utilizing the chemical properties of 4-aminobenzonitrile, existing pesticide active ingredients can be modified and improved. By introducing 4-aminobenzonitrile structural units into pesticide molecules, the physicochemical properties and biological activity of pesticides can be altered. For example, increasing the lipid solubility of pesticide molecules, improving their permeability and conductivity in plants, and enhancing the control effect of pesticides;
Alternatively, adjusting the polarity of pesticide molecules can reduce their environmental pollution and toxicity to non target organisms, thereby improving the safety and environmental friendliness of pesticides.
Auxiliary components of pesticide formulations
4-aminobenzonitrile can also serve as an auxiliary ingredient in pesticide formulations, playing a certain role. It can be used as a solvent, dispersant, or stabilizer to improve the performance of pesticide formulations. As a solvent, it can dissolve some pesticide active ingredients that are difficult to dissolve in water, improving the solubility and dispersibility of pesticides;
As a dispersant, it can prevent the aggregation of pesticide particles, so that the pesticide can be evenly dispersed on the target surface during the spray process; As a stabilizer, it can inhibit the decomposition and deterioration of pesticides, extending their shelf life.
adverse reaction
4-aminobenzonitrile, as an important organic compound, has a wide range of applications in various fields such as medicine, dyes, pesticides, and materials science. In the field of medicine, it is a key intermediate for synthesizing various drugs and participating in the construction of drug molecular structures with specific biological activities; In the dye and pigment industry, it can be used to synthesize various brightly colored and high-performance dyes and pigments; In pesticide synthesis, it can be used as an important raw material to prepare highly efficient and low toxic insecticides, fungicides, etc; In the field of materials science, it can also be used for synthesizing polymer materials and functional materials. However, with its increasingly widespread application, the potential adverse reactions that 4-aminobenzonitrile may cause have gradually attracted attention.
Acute Toxicity
Oral toxicity
Animal experiments have shown that 4-aminobenzonitrile has certain oral acute toxicity. When experimental animals ingest a large dose of 4-aminobenzonitrile at once, a series of toxic symptoms will appear in a short period of time. Mild cases may manifest as loss of appetite, mental lethargy, reduced activity, etc; As the dosage increases, symptoms such as vomiting, diarrhea, and difficulty breathing may occur, which can lead to coma or even death in severe cases. The lethal dose varies depending on factors such as animal species, age, and health status. For example, in mouse experiments, the median lethal dose (LD50) was within a certain range, indicating that if ingested in large quantities, the human body may also face serious health threats.
Skin Contact Toxicity
Direct contact with 4-aminobenzonitrile solid or its solution can cause acute adverse reactions on the skin. Exposure to high concentrations of substances in a short period of time may cause symptoms such as redness, swelling, pain, itching, and in severe cases, damage such as blisters and ulcers may occur on the skin. This is because 4-aminobenzonitrile has a certain degree of irritation and corrosiveness, which can damage the normal structure and function of the skin, causing damage to the skin barrier and triggering inflammatory reactions. Moreover, if not cleaned in a timely manner after skin contact, substances may be absorbed into the body through the skin, causing systemic poisoning symptoms.
Inhalation toxicity
During the production and use of 4-aminobenzonitrile, if there is poor ventilation, its dust or vapor may be inhaled into the human body, leading to acute respiratory poisoning. After inhalation, patients will quickly experience symptoms such as coughing, sputum production, wheezing, and difficulty breathing. In severe cases, it can lead to chemical pneumonia or pulmonary edema. This is because 4-aminobenzonitrile has a strong irritant effect on respiratory mucosa, which can cause pathological changes such as mucosal congestion, edema, and increased secretion, affecting gas exchange and respiratory function.
Chronic Toxicity
Damage to the liver
Long term exposure to low-dose 4-aminobenzonitrile may cause chronic damage to the liver. The liver is an important detoxification organ in the human body. After 4-aminobenzonitrile enters the body, most of it undergoes metabolic transformation in the liver. During this process, some toxic metabolites may be produced, which can interfere with the normal metabolism and function of liver cells, leading to liver cell damage, necrosis, and ultimately causing liver inflammation, fibrosis, and other lesions. Long term accumulation may lead to abnormal liver function, manifested by changes in indicators such as elevated serum transaminase and bilirubin levels. In severe cases, it can develop into irreversible liver diseases such as cirrhosis.
Effects on the kidneys
The kidney is also one of the target organs for chronic toxicity of 4-aminobenzonitrile. After long-term exposure to this substance, it and its metabolites may reach the kidneys through blood circulation, accumulate in the kidneys, and cause damage to structures such as renal tubules and glomeruli. The renal tubules are an important part of the kidney's reabsorption and secretion functions. Injury can lead to changes in urine composition, such as proteinuria and tubular urine; Glomerular injury can affect the filtration function of the kidneys, leading to the accumulation of metabolic waste such as creatinine and urea nitrogen in the body, resulting in renal dysfunction.
Effects on the nervous system
Long term exposure to 4-aminobenzonitrile may also have chronic adverse effects on the nervous system. Patients may experience symptoms such as headache, dizziness, fatigue, insomnia, and memory loss. In severe cases, it can affect the normal function of the nervous system and lead to diseases such as neurasthenia syndrome. This may be due to the direct toxic effects of 4-aminobenzonitrile and its metabolites on nerve cells, which interfere with the synthesis, release, and metabolism of neurotransmitters, affecting the transmission of nerve impulses and the normal regulatory function of the nervous system.
Skin and eye irritation
Skin irritation
In addition to skin damage caused by acute contact, long-term repeated exposure to low concentrations of 4-aminobenzonitrile may also lead to chronic skin irritation symptoms. It manifests as dry, rough, cracked, and flaky skin, and in severe cases can cause skin pigmentation or eczema like changes. This is because 4-aminobenzonitrile continuously stimulates the skin, disrupting the skin's barrier function and normal metabolism, leading to a decrease in skin defense ability and easily causing various skin problems.
Eye irritation
When dust or vapor of 4-aminobenzonitrile enters the eyes, it immediately causes strong eye irritation symptoms such as eye pain, tearing, photophobia, conjunctival congestion, etc. If not treated in a timely manner, it may lead to corneal damage and affect vision. This is because the ocular mucosa is very sensitive, and the stimulation of 4-aminobenzonitrile can directly damage the corneal and conjunctival epithelial cells, causing ocular inflammatory reactions. In severe cases, it can leave sequelae such as corneal scars, causing permanent damage to vision.
Effects on the Reproductive System and Development
Effects on the Reproductive System
Animal experiments have found that 4-aminobenzonitrile may have adverse effects on the reproductive system. After contact with male animals, testicular tissue lesions may occur, affecting the generation and quality of sperm, leading to a decrease in sperm count, decreased vitality, and increased deformity rate, thereby affecting fertility. After contact with female animals, it may interfere with the normal function of the ovaries, affect egg development and ovulation, lead to reproductive endocrine disorders, and affect fertility and embryonic development.
Effects on Development
During embryonic development, if the mother comes into contact with 4-aminobenzonitrile, it may enter the fetus through the placental barrier and have adverse effects on fetal development. May lead to fetal growth retardation, deformities, such as limb deformities, abnormal neurological development, etc. This is because fetuses are more sensitive to harmful substances during development, and 4-aminobenzonitrile and its metabolites may interfere with the normal division, differentiation, and growth of fetal cells, leading to developmental abnormalities.
Potential Carcinogenicity
At present, there is insufficient research on the potential carcinogenicity of 4-aminobenzonitrile, but some compounds with similar structures have carcinogenicity, so it cannot be ruled out that 4-aminobenzonitrile also has carcinogenic risks. Long term exposure to this substance may increase the likelihood of cancer in the human body, and its carcinogenic mechanism may be related to causing cellular DNA damage, gene mutations, interference with cellular signaling, and thus leading to uncontrolled cell proliferation and the occurrence of malignant tumors.
Other special adverse reactions
In certain special circumstances, 4-aminobenzonitrile may also cause other adverse reactions. For example, when mixed with certain chemicals, chemical reactions may occur to produce more toxic substances, leading to more severe poisoning symptoms; Under special conditions such as high temperature and high pressure, the properties of 4-aminobenzonitrile may change, increasing its danger and the risk of adverse reactions.
Reference
[1] Zhang, Y., & Liu, H. (2021). Functional group transformation and pharmaceutical intermediate application of 4-aminobenzonitrile.Journal of Pharmaceutical Chemistry Research, 45(8), 621-628.
[2] Wang, L., Chen, J., & Zhao, M. (2022). Design and synthesis of novel targeted antitumor drugs based on 4-aminobenzonitrile skeleton. European Journal of Medicinal Chemistry, 239, 114562.
[3] Li, S., & Yang, X. (2020). Derivatization application of 4-aminobenzonitrile in high-performance liquid chromatography drug detection. Journal of Chromatography A, 1625, 461329.
[4] Chen, H., et al. (2019). Synthesis optimization and antibacterial activity evaluation of 4-aminobenzonitrile-derived heterocyclic compounds. Chemical & Pharmaceutical Bulletin, 67(12), 1358-1364.
[5] Gao, R., & Zhou, B. (2023). Mild catalytic conversion of amino and cyano groups of 4-aminobenzonitrile for drug molecular modification. Journal of Organic Chemistry, 88(5), 3210-3217.
Frequently Asked Questions
Q1: What quality documents can you provide when purchasing 4‑Aminobenzonitrile?
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A: For every order of 4‑Aminobenzonitrile, Bloomtechz can provide batch‑specific COA, MSDS and related qualification files. These documents support your internal testing review, experimental traceability and project filing. We can also adjust document formats according to reasonable customer requirements.
Q2: Can you deliver both lab‑scale sample orders and large‑volume commercial batches of 4‑Aminobenzonitrile?
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A: Yes. Bloomtechz supports flexible order sizes from small laboratory sample trials to mass‑scale commercial production. Multiple packaging options are available. Samples and bulk goods follow identical quality control standards, and our sales team keeps clients updated on production and logistics progress in real‑time.
Q3: Is customized service available for 4‑Aminobenzonitrile?
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A: Partial customization is acceptable. If you have special requirements on purity index, moisture content, packaging form or impurity control, please share your detailed technical indicators. Our technical department will conduct feasibility assessment and give feedback on process possibility, lead time and corresponding quotation.
Q4: How do you handle shipment and packaging for 4‑Aminobenzonitrile?
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A: 4‑Aminobenzonitrile adopts moisture‑proof sealed packaging suitable for fine‑chemical solids. Bloomtechz selects proper packaging specifications according to order quantity. We cooperate with professional chemical logistics providers to ensure safe transit. We can also offer special packaging solutions to meet export and dangerous‑goods transportation requirements.
Q5: What kind of technical support can I get after receiving goods?
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A: After delivery, Bloomtechz keeps open technical support channels. If you encounter abnormal phenomena such as poor solubility or unexpected experimental performance during application, you may feed back test details to our team. We will assist in analyzing possible causes and give practical suggestions for your synthesis process.
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