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O-Aminobenzonitrile has roots in the golden age of synthetic chemistry, cropping up as chemists chased routes to aromatic amines in the late nineteenth century. Most folks working with aromatic compounds can trace the logic: combining the reactivity of the amino group with the utility of the nitrile gave chemists a flexible building block. By the early 1900s, industrial laboratories began refining production, folding the compound into broader dye, drug, and specialty chemical applications. The ongoing pursuit for improved pharmaceuticals and pigments in the last century pulled O-Aminobenzonitrile out of the academic curiosity cabinet and into pilot plants and warehouses worldwide. Every decade saw greater demand, measured by patent filings and published methods, as researchers sought more efficient synthesis and higher yields. The compound’s reputation spread, linking the name to innovation in both small-scale labs and sprawling chemical factories.
O-Aminobenzonitrile, sometimes called 2-Aminobenzonitrile, emerges as a colorless to pale yellow crystalline solid. Its sharp, faintly bitter odor hints at its aromatic nature, much like its cousins aniline and benzonitrile. Chemists value it for its dual reactivity: the amino group brings nucleophilicity, the nitrile opens doors to further functionalization. Industries hunting for efficient raw materials often reach for this compound as a stepping stone in multi-step synthesis, whether for agrochemicals, polymer precursors, or pharmaceutical scaffolds. Its availability from chemical suppliers, typically at technical and analytical grades, underlines its importance across multiple commercial and research streams.
This molecule’s melting point lands just under 50°C, and it boils closer to 280°C, reflecting the stability of its aromatic core. Solubility can be a struggle: water barely dissolves it, but alcohols and acetone do a better job. O-Aminobenzonitrile holds up under normal atmospheric conditions, but prolonged heat or UV light can kick off slow decomposition or discoloration. Its amino group at the ortho position brings electron-donating tendencies, activating the ring for further reaction—something process chemists use to their advantage. Its nitrile group, though less reactive, quietly sets the stage for transformations like hydrogenation or hydrolysis. Chemically, this mix of groups means it easily slips into pathways for heterocycle formation and condensation reactions.
Chemical suppliers package O-Aminobenzonitrile under the name 2-Aminobenzonitrile and mark containers with CAS number 88-85-7. Labeling typically lists purity, which ranges from 97% in technical grades up to over 99% for analytical needs. Net weight, batch number, production date, and hazard statements—such as flammability, toxicity, and advice on protective gear—feature on the container. The safety data sheet (SDS) comes standard, outlining chemical hazards in compliance with OSHA and international GHS standards. Producers emphasize lot traceability for pharmaceutical customers and often provide IR or NMR spectroscopic data, ensuring chemists know exactly what they are working with in their flask.
Synthesis has evolved from early halogenation-and-amination approaches toward more elegant direct methods. The Sandmeyer reaction stands out, using o-aminobenzyl chloride and copper catalysts in aqueous or alcoholic media to construct the nitrile. In modern labs, palladium-catalyzed cross-coupling offers another route, handing chemists improved selectivity and fewer byproducts. Large scale producers lean into these newer catalytic methods, since fewer impurities make downstream purification easier. Older nitration-then-reduction schemes, though simple, tend to create environmental waste, nudging manufacturers toward greener alternatives like transition-metal catalysis or enzymatic conversion. Raw material cost, yield, and ease of waste management often tip the scales in deciding which route gets used.
Researchers find the amino group in O-Aminobenzonitrile to be a welcoming entry point for acylation and diazotization. Condensation reactions open doors to heterocycles like benzimidazoles and quinazolines, compounds central to today’s medicinal chemistry projects. The nitrile group won’t sit idle; under acidic or basic hydrolysis, it converts to carboxylic acids or amides, feeding materials into agricultural or pharmaceutical synthesis. Its structure invites reduction, producing ortho-toluidines for dyes, while oxidative coupling can lead to azo linkages—well known in pigment production. Both groups play supporting roles in multi-step syntheses, giving scientists flexibility in designing new pathways. Industrial chemists patch these reactions into stepwise procedures to maximize throughput and minimize waste.
Ask around in any chemistry lab or specialty catalog and the names 2-Cyananiline, Benzonitrile, 2-amino-, and O-Cyanoaniline crop up next to O-Aminobenzonitrile. Trade labels sometimes just stick with the CAS number for streamlined ordering. Regional naming conventions in Asia and Europe add local language variations; suppliers standardize on IUPAC recommendations to keep confusion at bay. Smaller regional distributors list synonyms to help researchers match local nomenclature with international norms—a lesson in the patchwork of science communication.
Handling O-Aminobenzonitrile calls for gloves, lab coats, and eye protection. Accidental skin contact can trigger irritation, and inhalation of dust or powder often causes coughing or respiratory discomfort. Chemical hygiene rules remind users to work with good ventilation and store the compound in a cool, dry area away from strong bases and acids. Fire risks sit low, but the compound does burn if exposed to open flames. Waste disposal gets close attention: residues and empty containers must be handled as hazardous according to local regulations. Emergency procedures, spill protocols, and first aid advice round out the safety documentation. Training aims to keep lab workers alert and avoid accidents in both academic and manufacturing environments.
O-Aminobenzonitrile bridges academic research and industrial production. Chemists studying heterocycle synthesis lean on its bifunctional nature to tweak pharmaceutical leads for bioactivity screens. Dye makers use it as an intermediate for vivid pigments reaching from textiles to printing inks. Polymer companies develop novel resins and engineering plastics, banking on the compound’s ability to introduce toughness or chemical resistance. Agrochemical laboratories scout for new herbicides or fungicides by modifying its core. In academic circles, researchers focus on new reaction cascades, probing mechanistic details and testing catalytic cycles to push the boundaries of efficiency. Electronics and advanced materials research features O-Aminobenzonitrile in pilot projects geared toward specialty coatings and semiconductors.
Scientists look to O-Aminobenzonitrile for new reaction development and better pathways to active pharmaceutical ingredients. Patent literature brims with examples of structure modifications that change biological activity—often starting from this core molecule. Pharmaceutical research pursues analogs of antipsychotic, antiviral, and anticancer agents, driven by the possibilities the amino and nitrile groups provide for functional group diversification. Catalysis studies push for cheaper, recyclable metal complexes to activate O-Aminobenzonitrile in mild conditions, targeting both process economics and sustainability. Computational chemistry groups model its electron distribution, aiming to predict reactivity in multi-step processes or help design greener syntheses. Open-access efforts spread, making experimental data and reaction outcomes available for global collaboration.
Analysis of toxicity shows O-Aminobenzonitrile carries risks, especially for those working without proper protection. Short-term exposure irritates the skin, eyes, and respiratory tract. Animal studies indicate moderate oral toxicity, with symptoms ranging from lethargy to labored breathing at high doses. Long-term effects haven’t been studied as thoroughly, but breakdown to potentially harmful metabolites and the presence of an aromatic amino group flag reasons for caution. Environmental agencies track release because nitriles in groundwater can threaten aquatic life. High performance liquid chromatography and mass spectrometry monitor workplace and environmental levels, helping regulators keep concentrations well below harmful thresholds. Recent research suggests safer analogs and treatment methods for spills, but industry must emphasize training and emergency readiness at every facility.
Demand for O-Aminobenzonitrile should grow as need for flexible synthetic routes increases in pharmaceutical, agricultural, and specialty materials industries. Advances in green chemistry hold promise for cleaner, safer production—especially as companies shift from legacy processes to greener catalysts and fewer hazardous reagents. Researchers keep hunting for new reactions that make use of both its amino and nitrile groups, looking to streamline cascade processes or improve selectivity for targeted products. Regulatory scrutiny will likely tighten, requiring more transparent tracking of environmental impact and exposure risks. Global collaboration could uncover sustainable routes, and open-access sharing of experimental methods will aid smaller labs and startups as much as big corporations. Upgraded analytical techniques, like real-time monitoring and machine learning models for process control, may lead to safer, more efficient manufacturing. New medical developments may stem from compounds built off the O-Aminobenzonitrile backbone, reflecting how classic molecules still drive science forward.
Most people won’t find O-Aminobenzonitrile on a drugstore shelf, but anyone curious about the chemicals behind much of modern innovation would do well to know something about it. This compound plays an important role in the world of aromatic amines and nitriles — the sorts of compounds chemistry students grind through textbooks to understand, and that chemists use every day to make practical things most folks use without a second thought.
O-Aminobenzonitrile stands out for its usefulness as a starting material. Factories and labs don’t use this molecule for its own sake, but as a springboard, helping to knit together all sorts of useful and necessary chemicals. Drug development, dye manufacture, and agrochemical synthesis all make use of this compound as a chemical precursor.
For me, memories come up from college days—flasks bubbling away with the telltale almond smell of aromatic nitriles, warnings from the safety officer ringing in my ears. It’s one of those chemicals that demands respect. Just a little bit of this stuff can get converted into compounds used to treat infections, color textiles, or protect crops. Take dyes, for example: O-Aminobenzonitrile helps create vivid colors that stay put in fabric, something I came to appreciate after too many ruined shirts from cheap dyes.
Medicinal chemistry also relies on this molecule. The pharmaceutical field draws plenty of interest because here, O-Aminobenzonitrile gives rise to substances that sometimes help make new antibiotics or cancer drugs. The amine and nitrile groups provide the chemical hooks chemists need to build more complex rings—a bit like starting a LEGO build with just the right bricks.
Discussion around chemical manufacturing always circles back to health and the planet. O-Aminobenzonitrile poses toxicity risks if handled without care, which I learned firsthand working late shifts in the lab. Gloves, fume hoods, and clear protocols aren’t fancy extras—they’re essential in keeping people safe. Production facilities have to pay attention to proper waste handling. Cyanide-containing chemicals bring real risk, and taste for shortcuts doesn’t mix with this kind of work.
Disposal matters too. Before flushing any waste, we needed to neutralize cyanide residues and document every step. This discipline comes from hard-won lessons across the world—a result of mistakes that led to environmental disasters. From rivers to lab floors, mishandling can have long legs.
Safer alternatives sit high on the wish list. Green chemistry stresses ways to design and use chemicals that limit hazards from the start—using catalysts that cut down on byproducts, or methods that don’t require harsh conditions. I’ve followed researchers working toward biosynthetic routes, where enzymes might someday perform the job instead of hazardous reagents.
Education makes a difference too. Every time industry or academia invests in better training for chemists, the safer the process becomes. The more public discussion includes these basic chemicals, the less mysterious—and less risky—them become in the hands of professionals.
O-Aminobenzonitrile is a workhorse in the background of modern chemistry, not a superstar, but critical in the chain leading to products we use daily. Easy to overlook, sure, but deserving of some time in the spotlight as we think about how to balance the benefits of chemical innovation and everyday safety.
O-Aminobenzonitrile doesn’t exactly grab headlines, but the chemical formula, C7H6N2, carries some solid weight in both research and industry. In simple terms, it’s a benzene ring with both an amino group (–NH2) and a nitrile group (–CN) hanging off it, sitting side by side on the ring. That closeness makes all the difference, especially if you’ve spent time mixing chemicals in a lab or taking apart molecular structures in textbooks.
On paper, O-Aminobenzonitrile looks unassuming, but the ortho-positioning of its amino and nitrile groups gives it a reactive edge. Those groups don’t just sit peacefully next to each other. Instead, they jostle and influence how the molecule reacts with other chemicals. The formula isn't just about ticking boxes on an exam: C7H6N2 reflects real relationships inside the molecule.
As someone who has followed organic syntheses, I’ve seen chemists lean on these kinds of compounds to build larger, more complex molecules. In drug development, creating links between these functional groups can produce future treatments — or speed up the hunt for a new one.
Few people walk into a pharmacy looking for O-Aminobenzonitrile, but its fingerprint shows up in dyes, pharmaceuticals, pesticides, and resins. Chemists often use it as a building block, not the finished product. For instance, its role in synthesizing benzotriazole derivatives has a downstream effect on corrosion inhibitors, which protect pipes and engines. Without those inhibitors, infrastructure breaks down faster, driving up repair costs and safety risks.
Lab researchers worldwide prize o-aminobenzonitrile for its dual-functionality. Working with a molecule that contains both –NH2 and –CN simplifies steps in multi-stage syntheses. Instead of piecing together fragments over several reactions, chemists can often leapfrog steps, saving not just money but time and energy. Every shortcut in the lab helps determine how soon a new compound arrives in medicine, industrial processing, or agriculture.
No story about chemicals feels real without a nod to the risks. Like other aromatic amines, O-Aminobenzonitrile deserves careful handling. Direct skin contact or inhalation can irritate the body, so gloves and fume hoods aren’t just fancy accessories, they’re non-negotiable safety measures. In my early lab days, a lapse in protocol cost a student their comfort for a week. This isn’t empty policy — it’s about health, liability, and keeping science moving.
Tighter safety standards have raised the bar for how companies and labs handle compounds like O-Aminobenzonitrile. Every spill reported and each material safety data sheet read is another step toward safer environments. Sometimes, the most responsible move comes from smaller adjustments: routine training, better labeling, and transparent risk communication between scientists, manufacturers, and workers.
The C7H6N2 formula might sit quietly in a database, but its presence stretches across chemistry, medicine, and manufacturing. Each innovation in one lab could trigger broader changes, reminding us that progress isn’t just the work of headline molecules — often, the least glamorous compounds open the biggest doors.
O-Aminobenzonitrile might sound like just another long name from an organic chemistry class, but the way it interacts with living systems puts real weight behind its presence in labs. This compound, used in research and certain pharmaceutical applications, brings more to the table than just synthetic utility. Its structure—a benzene ring with both an amino and a nitrile group—means it carries reactivity that shouldn’t be underestimated.
During my time in the lab, opening a new bottle of o-aminobenzonitrile drew a silent respect from those who’d read the safety data sheets. This substance irritates the eyes and skin; breathing dust from it brings coughing or choking. Lapses in safe handling don’t just cause discomfort—they can knock you off your feet for the day. A friend once worked without the right gloves, thinking he’d get away with a “quick transfer.” Skin contact brought out redness and pain within minutes, and he learned fastest from experience.
Animal studies point to acute toxicity if this chemical gets inside the body. It can enter through skin, by swallowing, or—more worryingly—by inhaling powders or vapors. Nitrile groups stand notorious for releasing cyanide under certain conditions. Even if this molecule sits in a solid state most of the time, exposure in the wrong way lets the body metabolize it, freeing up hazardous compounds that upset the body's oxygen use. That isn’t speculation. Researchers found cases of methemoglobinemia and other oxygen transport issues in tests involving similar cyanide-releasing compounds.
Exposure over weeks or months turns the story darker. Chronic inhalation or skin absorption can affect the nervous system. Lab safety culture now makes sure to prevent low-level contact, because repeated complaints of headaches, dizziness, or weakness appeared in poorly ventilated spaces. Beyond the body, spills that escape into water or soil pose another headache, since degradation can still lead to cyanide, risking local wildlife and drinking water supplies.
The material safety data sheets rate o-aminobenzonitrile as harmful or toxic by ingestion and inhalation. It sits on hazard lists for a reason. International guidelines from organizations such as the European Chemical Agency and US OSHA recommend gloves, goggles, lab coats, and mechanical ventilation systems for good reason—not bureaucracy, but proof from medical journals and workplace injury reports. The stories aren’t limited to textbooks. Limits on workplace air concentrations exist for compounds just like it, and responsible labs enforce them, because even one exposure can lead to weeks of misery—or worse.
Fume hoods, protective clothing, and strict waste management go further than rules—they protect your lungs, skin, and communities. In my own work, a well-maintained lab culture put safety before speed. Labeling every bottle and making sure every new team member watched a chemical safety video wasn’t overkill. It’s putting facts and compassion into action, making sure research keeps moving forward without risking harm to folks in the lab or anyone outside.
Folks who have come across O-Aminobenzonitrile in a lab might recognize its distinctive solid form at room temperature. With its chemical formula C7H6N2, it weighs in at about 118.14 grams per mole. One glance at the pale yellow to light brown powder, and it’s clear this isn’t your average household chemical. This compound doesn’t just look different — it smells different too, carrying a faint but sharp odor that sticks around the longer you work with it.
I’ve seen that O-Aminobenzonitrile starts to melt around 45-51 °C. Once you heat it past 285 °C, it boils. Because it sits in that low-melting, high-boiling range, it stays stable through a lot of conditions you’d encounter in research and manufacturing. Scientists and engineers pay close attention to these properties, since it determines what types of reactions it can withstand and how safely it can be transported or stored.
This compound doesn’t dissolve easily in water. If you dropped some into a beaker, you’d see most of it settle at the bottom like wet sand. On the other hand, organic solvents like ethanol or acetone break it up well, so folks handling it in synthesis or purification prefer these liquids. Solubility shapes a lot about how a chemical gets used. For instance, it means folks handling wastewater treatment or environmental monitoring need to keep an eye on where this compound might turn up and how best to deal with contamination — because it won’t simply wash away with the rain.
O-Aminobenzonitrile’s density lands at around 1.16 grams per cubic centimeter. At first touch, this makes it feel less “heavy” compared to some inorganic powders like salts or oxides. Its fine, somewhat gritty texture means it doesn’t clump too easily, which, in my experience, makes measuring and transferring it between containers much less of a chore. People who handle chemicals in bulk pick up quickly how much easier it becomes to work with solids that don’t form troublesome lumps.
The distinct smell and solid state raise some important points. Volatility isn’t off the charts, but dust can still irritate skin and lungs. Based on what safety data sheets and long hours at the bench tell us, goggles and a dust mask aren’t just for show. I always made a point to double-check the local ventilation, because the aromatic amine core means vapors aren’t great for you over time. These practical realities push researchers and managers to set clear rules in handling and storage, reducing fire and health risks for everyone involved.
Chemical manufacturers lean on O-Aminobenzonitrile as a building block, mainly because the amino and nitrile groups make it versatile. Purity levels often depend on careful handling during heating and separation, and that all ties back to knowing things like melting point, boiling point, and solubility. For folks developing new pharmaceuticals or pesticides, being able to predict its behavior at every stage really matters. Mistakes in storage or mixing can ruin batches and waste resources, so experience working hands-on with the compound helps refine these processes.
Training and infrastructure both help reduce risk with any compound like O-Aminobenzonitrile. Laboratory teams benefit from clear information on safe temperatures and which solvents work best. Practical tools — like well-sealed storage jars and regular checks for spills — make a difference every day. Investing up front in robust workplaces doesn’t just prevent trouble; it builds a safer foundation for sustainable chemistry down the line. Every property, once you get to know it, shows a new angle for doing the job better and safer — both for people and for the planet.
O-Aminobenzonitrile finds use in labs and factories handling organic synthesis, dye production, and pharmaceuticals. The compound looks like a light-colored crystalline powder. Smelling it up close catches a strong odor, hinting at the risk: O-Aminobenzonitrile can irritate eyes, skin, and the respiratory tract. Too much exposure leaves a person dizzy or nauseated, and in extreme cases, it can lead to more severe symptoms.
During a stint at a university research lab, I saw firsthand how proper storage impacts everyone’s health. Colleagues sometimes overlooked basic safety, but one mishap cleared up any hesitation. O-Aminobenzonitrile stores best in a sturdy, tightly sealed glass or HDPE container. Keeping the container labeled and out of sunlight reduces breakdown and contamination. Warm spaces speed up chemical reactions, so picking a cool, ventilated chemical cabinet makes sense. Don't keep it near food, acids, or oxidizing agents. Water or humidity inside the storage gives rise to unwanted side reactions.
I learned to keep incompatible materials far apart. Once, our inexperienced team member placed a nitrile bottle next to bleach, not thinking twice. That week, our storage review found the issue before it turned into an accident, but it drove home the lesson: O-Aminobenzonitrile doesn’t mix well with oxidizers. Even a little spill nearby threatens a hazardous reaction.
Simple gloves don’t always cut it. At work, I watched a coworker ignore the Material Safety Data Sheet and opt for thin latex gloves, only to develop a mild rash. After that, everyone stuck to using proper chemical-resistant gloves—nitrile or neoprene—plus goggles and a long-sleeved lab coat.
Ventilation matters too. Processing or weighing the substance in an open room kicks up dust, which sneaks into the airways. A fume hood saves the day, keeping exposure levels down and providing peace of mind. After each session, washing hands and cleaning the bench with a damp, disposable cloth cut down the chances of skin contact and unintended mixing.
Nobody plans for spills, but accidents land in an instant. If any powder escapes, gently sweeping it up with a dustpan avoids stirring more into the air. Bagging the waste tightly and marking the package for hazardous waste ensures nobody mistakes it for regular trash. Local disposal rules guide the final step; dumping it in the drain or garbage risks polluting water and endangering sanitation workers.
Training every new team member in these steps keeps everyone safe. Running regular reviews of handling procedures prevents complacency. Many small lapses add up, and I’ve seen the relief on a manager’s face after an audit turned up zero issues.
Switching to safer substitutes, if the project allows, takes some strain off. Where O-Aminobenzonitrile stays essential, strengthening supply chain checks ensures that only those trained and equipped keep access. Good labeling, updated record-keeping, and close teamwork create a safer lab culture. Fostering open conversation about risks, rather than brushing them aside, builds trust and saves time in the long run.
Storing and handling O-Aminobenzonitrile calls for vigilance, smart habits, and learning from close calls. The right steps keep both science and people safe.
| Names | |
| Preferred IUPAC name | 2-Aminobenzenecarbonitrile |
| Other names |
2-Aminobenzonitrile o-Cyananiline o-Aminobenzonitrile |
| Pronunciation | /ˌoʊ.əˌmiːnoʊ.bɛnˈzoʊ.nɪˌtraɪl/ |
| Identifiers | |
| CAS Number | 88-45-9 |
| Beilstein Reference | 1209246 |
| ChEBI | CHEBI:72836 |
| ChEMBL | CHEMBL50474 |
| ChemSpider | 15766 |
| DrugBank | DB08374 |
| ECHA InfoCard | 100.047.057 |
| EC Number | 208-679-2 |
| Gmelin Reference | 84148 |
| KEGG | C08389 |
| MeSH | D000569 |
| PubChem CID | 70031 |
| RTECS number | CU1400000 |
| UNII | 7RN67U30G6 |
| UN number | UN3439 |
| CompTox Dashboard (EPA) | DTXSID4018408 |
| Properties | |
| Chemical formula | C7H6N2 |
| Molar mass | 118.14 g/mol |
| Appearance | Light yellow to brown solid |
| Odor | Ammonia-like |
| Density | 1.17 g/cm³ |
| Solubility in water | Slightly soluble |
| log P | 1.41 |
| Vapor pressure | 0.08 mmHg (25°C) |
| Acidity (pKa) | 1.98 |
| Basicity (pKb) | 2.05 |
| Magnetic susceptibility (χ) | -37.5·10⁻⁶ cm³/mol |
| Refractive index (nD) | 1.595 |
| Viscosity | 0.96 cP (20°C) |
| Dipole moment | 3.97 D |
| Thermochemistry | |
| Std molar entropy (S⦵298) | 156.6 J·mol⁻¹·K⁻¹ |
| Std enthalpy of formation (ΔfH⦵298) | 123.7 kJ/mol |
| Std enthalpy of combustion (ΔcH⦵298) | -3082 kJ/mol |
| Hazards | |
| Main hazards | Harmful if swallowed, in contact with skin or if inhaled. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation. |
| GHS labelling | GHS02, GHS07 |
| Pictograms | GHS07 |
| Signal word | Warning |
| Hazard statements | H301, H315, H319, H332 |
| Precautionary statements | P261, P264, P271, P272, P280, P302+P352, P304+P340, P312, P321, P363, P405, P501 |
| Flash point | 170°C |
| Autoignition temperature | 640°C |
| Explosive limits | Explosive limits: 2.8–13% |
| Lethal dose or concentration | LD50 oral rat 1210 mg/kg |
| LD50 (median dose) | LD50 (median dose): 2100 mg/kg (oral, rat) |
| PEL (Permissible) | PEL (Permissible Exposure Limit) for O-Aminobenzonitrile: "Not established |
| REL (Recommended) | 1 mg/m3 |
| IDLH (Immediate danger) | Unknown |
| Related compounds | |
| Related compounds |
Benzonitrile Aniline M-Aminobenzonitrile P-Aminobenzonitrile 2-Nitrobenzonitrile |
