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3-Chloropropionitrile: A Closer Look at a Small But Mighty Chemical

Historical Development

3-Chloropropionitrile has quietly woven itself into the fabric of chemistry since the early 1900s, when researchers in Europe first experimented with nitriles and their halogenated cousins. Early patent literature captured the compound’s production as a side-note in the race to synthesize more complex pharmaceuticals and agrochemicals. As a chemistry student, I remember running into it in our third-year lab manual, hidden beneath bulkier reagents but silently tying reactions together. Its roots stretch back to a time when the world looked to small molecules to solve big problems, a legacy that still colors its reputation today.

Product Overview

It may look modest—a colorless liquid, no dramatic scent, no flamboyant hue—but 3-Chloropropionitrile packs chemical punch. The molecule’s structure hosts a striking dynamic; a three-carbon chain capped with a nitrile on one end and a chlorine atom on the other. The chemical formula, C3H4ClN, points to a small, light structure, but there’s subtlety in the way its functional groups spark reactivity. Its versatility as a building block anchors it in the labs of organic chemists chasing new pharmaceuticals, flavoring agents, and specialty polymers.

Physical & Chemical Properties

3-Chloropropionitrile boils at around 145°C, which fits the profile for small organic nitriles. Its density sits near 1.08 g/cm³, so it pours like a light oil. The molecule barely mixes with water, instead dissolving easily in organic solvents like acetone or diethyl ether—no mystery there, given its polar and nonpolar ends. The nitrile group makes it pretty stubborn toward basic hydrolysis, but acids can open up the triple bond to steer new chemistry. Its vapor is heavier than air, raising safety flags whenever large quantities come into play.

Technical Specifications & Labeling

Regulators flag 3-Chloropropionitrile as an acutely toxic liquid. Labels in industry settings highlight toxic inhalation and ingestion risks, skin absorption potential, and strong eye irritation hazard. Storage often means airtight glass or steel, far from oxidizers and water. Engineers design piping and valves around corrosion control, since the compound eats away at some plastics and soft metals. Productions specs call for high purity—usually above 98%—because leftover chlorides or other nitriles skew downstream reactions. Much of this echoes the day-to-day reality for chemists, where a chemical’s numbers can spell either a successful synthesis or a hazardous cleanup.

Preparation Method

Synthesizing 3-Chloropropionitrile rarely makes headlines, but the chemistry isn’t trivial. One widely used route involves reacting acrylonitrile with hydrogen chloride, sometimes relying on copper catalysts to force the addition. This process carries its own risks—acrylonitrile is flammable and toxic, hydrogen chloride is corrosive and volatile, and catalyst choice determines yield efficiency. Some labs opt for alternative routes, like halogen exchange from bromopropionitrile, but costs and waste often make the HCl pathway more practical on scale. Each choice in synthesis reflects a balancing act between cost, safety, and environmental responsibility—a reality vivid to anyone who’s managed a reaction flask into the late hours.

Chemical Reactions & Modifications

The business end of 3-Chloropropionitrile lies in its reactivity. That chlorine atom gets swapped easily for other groups, opening pathways to amines, sulfides, and more. Nucleophiles eye up the carbon-chlorine bond, snapping onto the molecule in ring-forming or chain-extending reactions. The nitrile doesn’t just sit on the sidelines either. Under carefully chosen conditions, reduction turns it into a primary amine—useful for everything from drugs to dyes. Acid or base hydrolysis transforms it into carboxylic acids, creating bridges to herbicides or specialty surfactants. Scientists wring more value from its chemical backbone by stringing new groups on both ends, a strategy I’ve seen drive patent filings in pharmaceuticals and fine chemicals for years.

Synonyms & Product Names

Digging into literature or the marketplace, you’ll see 3-Chloropropionitrile popping up under several aliases. Chemists often call it beta-chloropropionitrile or 3-chloropropanenitrile. CAS registries and international naming conventions leave little room for confusion once you line up the numbers, but in daily workflow, a synonym can matter. I’ve seen misplaced shipments from confusing “beta-chloro” with “gamma-chloro,” a mistake avoidable only with careful double-checking—something every synthetic chemist learns the hard way.

Safety & Operational Standards

3-Chloropropionitrile carries notable hazards—the kind that stick with you after a training demo or first spill. The molecule vaporizes subtly, risking inhalation exposure before anyone notices. Direct skin or eye contact leads to irritating burns or worse, thanks to easy tissue penetration. The nitrile group can break down inside the body to yield cyanide, calling for chemical-resistant gloves, full goggles, and powerful fume hoods during transfers or reactions. Many countries assign the compound to priority lists for health and environmental controls. Spills demand elaborate cleanup—think absorbent pads, neutralization solutions, and strict waste segregation. Emergency showers and eyewash stations don’t gather dust in facilities that use this chemical; everyone with gloves-on experience learns that lesson early.

Application Area

The best testament to 3-Chloropropionitrile’s value comes from where it ends up—a quick scan through patents or supplier catalogs lays out a global map. Agrochemical firms transform it into intermediates for selective herbicides. Pharmaceutical R&D uses it as a building block when assembling complex heterocycles or tweaking lead compounds. Polymer labs tap it for special monomer synthesis, steering toward niche plastics or protective coatings. Flavoring and fragrance teams, though less frequently, pursue its transformation into sharp-tasting precursors or aroma-rich molecules. Each application draws on the reactive balance between nitrile and chlorine—a balance that separates functional products from unachievable reactions.

Research & Development

Innovation with 3-Chloropropionitrile tends to bubble up near the interface of synthetic chemistry and applied molecular design. In my own academic orbit, I’ve watched teams claim breakthroughs by unlocking safer or greener production routes—sometimes swapping out hazardous reagents for benign alternatives or shifting to continuous flow techniques. Others chase catalytic systems that stretch yield or selectivity, all while keeping environmental impacts close to zero. Research often circles back to safety, searching for better ways to detect spills or neutralize toxic byproducts. Journals keep turning out fresh ideas, suggesting that the compound’s heyday might still sit ahead, driven by the evolving demands of pharmaceuticals, agrochemicals, and specialty polymers.

Toxicity Research

Toxicologists keep a watchful eye on 3-Chloropropionitrile. Acute exposure risks extend beyond routine irritation: its metabolism can liberate cyanide, sparking concern in both lab and industrial settings. Inhalation studies flag risks at surprisingly low concentrations. Animal models show nervous system and respiratory stress if management slips even slightly. These dangers focus efforts on engineering controls and robust protocols—process containment, scrubbers for exhaust, remote handling tools. Workplace monitoring backs up written rules with real-world assurance. Researchers dig into environmental fate, too, tracing breakdown products in soil and water while weighing long-term ecosystem impacts. Facts matter more than speculation here, because missing a detail can swing risk assessments and regulatory reviews.

Future Prospects

Looking ahead, 3-Chloropropionitrile seems poised for a stronger role in specialty and green chemistry. Market forces haven’t dented its importance as a backbone for fine and specialty chemicals—the compound keeps pulling its weight thanks to unique reactivity and scalable production. Emerging greener synthesis routes promise to chip away at legacy safety concerns, possibly shifting the industry from hazardous reagents toward less toxic alternatives with similar reactivity. The relentless drive for new drugs and specialty materials keeps innovation moving forward, demanding more precise and environmentally conscious use of building blocks—including 3-Chloropropionitrile. For anyone building molecules or improving the science of synthesis, its story reads less like a fading chapter and more like a stepping-stone toward the next advance in chemical technology.




What is 3-Chloropropionitrile used for?

Putting Chemistry to Work: 3-Chloropropionitrile in Industry

Some chemicals never get talked about outside a lab. 3-Chloropropionitrile is one of those hidden workhorses shaping products behind the scenes. It looks innocent—a colorless liquid with a faint, bitter scent—but this chemical packs some punch. With plenty of experience in industrial settings, I’ve seen how much 3-Chloropropionitrile does in the background and why companies pay attention to safety and supply chain logistics wherever it comes up.

Building Blocks in Pharmaceuticals

Many pharmaceutical ingredients start life as something simple. 3-Chloropropionitrile is a starting material for active molecules and intermediates in medicine production. Chemists use it for its reactive nature—adding that chlorinated fragment helps transform it into things like beta-amino acids and other key structures. Take anticonvulsant or anti-infective drugs, for example. Quite a few rely on building blocks where 3-Chloropropionitrile played a role somewhere down the line. Without access to this chemical, some synthesis pathways would stall out or become far more expensive.

Agrochemical Production: Protecting Crops

Agriculture demands innovations just to keep up with pests and plant diseases. 3-Chloropropionitrile is part of the toolkit for making herbicides, fungicides, and growth regulators. Its structure makes it easy for chemists to add a three-carbon chain where they need it, tweaking the properties of agrochemical compounds. Farmers may never see this liquid, but its fingerprints show up in better crop yields and food security. Companies value reliable supply, but they also have to manage risks because the chemical can cause problems if handled carelessly.

The World of Dye and Polymer Industries

Anyone fixing up new textiles, plastics, or advanced materials bumps into intermediates like 3-Chloropropionitrile. It’s not something on store shelves, but it kicks off the pathways to special dyes and functional polymers. The cyano (nitrile) group in the molecule lets it participate in reactions forming tough polymer chains or creating colorants that stick to fabric for years. Every time I see those tough, colorful plastic parts in houses and cars, I remember how something obscure like 3-Chloropropionitrile became essential at step one in the process.

Risks & Responsibility

No one in industry takes the safety of chemicals like 3-Chloropropionitrile lightly. It can cause irritation and even long-term health issues if managed poorly. I’ve seen places set strict safety protocols: fume hoods, double-gloving, and clear spill procedures. Everyone working with it goes through detailed training. Regulations from agencies like OSHA and the EPA are not just paperwork—they force a culture where chemical handling is taken seriously. Community health and environmental safety depend on observing all those controls, from delivery to final use.

Building Better Chemistry for the Future

Companies keep looking for new ways to use 3-Chloropropionitrile, but they also hunt for alternatives that might offer less risk or lower environmental impact. Green chemistry programs, safer work practices, and strong supplier vetting matter more than ever. In my view, the future of chemicals like this one depends on balancing technological progress with transparency and responsibility. That balance keeps supply chains running and communities safe, all while molecules like 3-Chloropropionitrile work quietly behind the scenes, shaping the products that improve lives every day.

What are the safety precautions for handling 3-Chloropropionitrile?

Understanding This Chemical

3-Chloropropionitrile isn’t exactly every chemist’s favorite. One whiff, and you know you’re dealing with a harsh, volatile compound. It can irritate eyes, skin, and lungs if given a chance. I remember working with similar nitriles during my time at a small research lab—one spill, and that sharp, choking smell hung in the air for hours. It made me extra cautious about safety, because health can turn on a dime with chemicals like this.

Personal Gear Cuts Risks

For this chemical, lab coats and splash-proof goggles aren't up for debate. Leave open shoes at home and cover skin as much as possible. Gloves matter: plain latex can break down quickly, so go for nitrile or butyl rubber. It’s not just about not getting burned—it’s about preventing chronic problems from repeated skin contact.

Shields or face protection come out when pouring large amounts. Even a small splash can sting. From my own experience, goggles fog up, and that bugs everyone. Even so, clearer vision never justifies skipping protection.

Keep Fumes Out of Your Lungs

Breathing vapors is a bigger deal than many realize. Once, a colleague thought the hood was off "just for a second"—ended up coughing for the rest of the afternoon. Always work under a functioning fume hood, with extraction fans running. Don’t trust the open window trick, not with this stuff.

If engineering controls can’t handle strong odors or accidental release, keep an approved respirator for organic vapors nearby. Even occasional work with this chemical can do long-term damage, so stick to best practices.

Why Labeling and Storage Matter

3-Chloropropionitrile may not look all that threatening in a beaker, but mishaps often start with confusion. Clear labeling saves a lot of headaches: write out the name, hazard symbols, and date. No one wants to guess what’s inside a vial, especially during a late shift.

Never store this chemical with acids, bases, or strong oxidizers. In my own work, a poorly labeled shelf led to a near miss—a bottle next to a strong acid started leaking. Store it in secondary containment, plastic bins or spill trays. Make sure the cap actually seals. Flimsy screw tops give way when you least expect it.

Spill Response and Disposal

If a spill happens, act fast. Know where the absorbent pads, neutralizers, and gloves are located before you start working—not after trouble hits. For small leaks, cover and soak up. For larger spills, evacuate and let trained professionals take over. I’ve seen someone try to wipe up a spill with a regular rag: that just spreads contamination and exposes skin. Big mistake.

Never pour leftovers down the drain. Most municipalities flag nitriles as hazardous waste. Seal material in an approved container, label it, and use a registered chemical waste service. Strict disposal keeps the water supply safe for everyone.

Training Makes Safety Stick

Shortcuts appeal when you’re late, hungry, or tired. Refresher training keeps those basic routines front-of-mind, so mistakes don’t compound. During my years in academic labs, annual drills and real-life stories made it clear: just one slip can change a career, or worse. Peer checks can help by catching missed steps, reminding everyone in the room why the rules matter.

Working with 3-Chloropropionitrile never gets routine enough to cut corners. Quality personal protective equipment, reliable ventilation, organized storage, and good training make all the difference. Clean habits protect more than your own health—they protect coworkers and the environment, too.

What is the chemical formula and structure of 3-Chloropropionitrile?

Breaking Down the Basics

A lot of folks in labs and chemical industries run into molecules like 3-chloropropionitrile more often than they might think. The chemical formula for 3-chloropropionitrile is C3H4ClN. This compact little compound carries both a nitrile group and a chlorine atom stuck on a three-carbon backbone. Let’s lay out its structure. You start with three carbons in a row. One end holds a nitrile (–C≡N), the other end gets a chlorine atom replacing one of its hydrogens (Cl–CH2–CH2–C≡N).

Structure in Simple Terms

Chemists like me draw it on paper as a straight-line chain. The nitrogen and chlorine pull the electrons around, giving polar ends. That structure lets 3-chloropropionitrile take part in a variety of reactions, which comes in handy both for researchers and those working with syntheses in larger factories.

What Sets 3-Chloropropionitrile Apart?

People notice this molecule shows up a lot because of how reactive it gets. The nitrile group on one end means you can shift it into different kinds of useful compounds—acids, amides, or amines with just a few tweaks. Over years in the lab, I’ve seen colleagues turn 3-chloropropionitrile into building blocks for medicines and agrochemicals.

The chlorine atom isn’t just for show. It’s a pretty good leaving group. That means in a warm flask with the right set of chemicals, it comes off to make way for something new. That opens doors to a whole world of substitutions, which chemists crave during new syntheses.

Why Chemists Rely on It

As someone who’s spent a fair bit of time doing organic reactions, 3-chloropropionitrile’s reliability stands out. It’s a staple—something you learn to trust because once you spot its formula on a bottle, you know you can take its chemistry to a lot of places. Many pharmaceutical intermediates start from molecules like this, especially when companies seek efficiency in getting from cheap starting materials to complicated end-products.

Years back, we used it to tweak the side chains of new drugs. A little modification on its tail, and a whole new set of biological activity appeared. The same goes in the world of crop protection—tweak the chain, and you either boost effect or drop toxicity.

Challenges with Safety and Handling

This compound isn’t something you want to treat carelessly. That chlorine can make things more hazardous: skin contact, inhalation, these bring trouble. Anyone handling 3-chloropropionitrile needs to rely on good ventilation and gloves. Regular training minimizes risk, but safety remains a personal habit.

Disposal gets tricky too. Standard organic waste procedures cover most of it, but rules shift between companies and locations. Relying on proper disposal keeps neighbors, coworkers, and water supplies protected. The chemical’s popularity in industry means regulators keep a close eye. That pressure for safety and transparency only grows as public awareness of chemical risks rises.

Looking for Solutions and Improvements

Chemists try green options these days, swapping out rougher chemicals for something less risky where possible. Some labs test out bio-based routes or catalysts that lower toxicity. While no magic bullet has replaced compounds like 3-chloropropionitrile yet, pushing for lower exposure, strong ventilation, and life-cycle awareness shows up in every responsible lab.

Innovation in chemistry always means wrestling with the balance of utility and risk. Experience across industry and research highlights that treating molecules like 3-chloropropionitrile with respect—both for their usefulness and their dangers—is the way forward.

How should 3-Chloropropionitrile be stored?

Recognizing the Risks

3-Chloropropionitrile doesn’t get much attention outside labs, but even a small mistake with this chemical can cause huge problems. This clear liquid smells faintly sweet, which can fool people into thinking it’s less hazardous than it really is. Inhaling its vapors, spilling it on the skin, or mixing it with the wrong stuff makes for a fast-track to both health and environmental trouble. I once watched someone, years ago, grab an unlabeled bottle during a crowded lab shift. They only realized it was 3-chloropropionitrile after catching the scent—luckily, no one got hurt. That close call stuck with me.

Good Storage Keeps Everyone Safe

Controlling temperature and air exposure means fewer accidents. 3-Chloropropionitrile likes cool, dry settings. Store it between two and eight degrees Celsius, away from heating systems, sunlight, and areas with shifting humidity. Keeping it away from direct light keeps the liquid stable and slows any chemical breakdown. Humidity opens the door for this compound to react, so dry storage stops any unwanted surprises.

Use tightly sealed containers—glass or certain compatible plastics work. This caps off vapor leaks and helps prevent spills, protecting staff from exposure. Steer clear of containers made out of metals that could react with the chemical, since that sets off its own dangers.

Labeling and Organization: No Shortcuts

Accurate labels matter more than most people think. One faded sticker can lead to confusion or disaster. I’ve seen labs go through near-misses all because someone found an unlabeled bottle shoved in the back of a shelf, and didn’t know what to do with it. Keep any vessel for 3-chloropropionitrile marked in bold, readable print. List hazard warnings, handling instructions, and the date it was received or poured. Store this chemical in a dedicated area, not mixed in with acids, bases, or oxidizers. It’s easy to see how a poorly-organized shelf could escalate a mess into a serious incident.

Segregation from incompatible chemicals sets up one more line of defense. Acids, bases, oxidizers, and strong reducing agents should all have their own homes. Cross-contamination triggers violent reactions that can harm people and destroy property.

Know the Emergency Plan

Preparedness saves lives. Every facility needs clear protocols for leaks or exposure. Anyone with access to 3-chloropropionitrile should know where the nearest eyewash and safety showers sit, how to operate ventilated hoods, and who to call if something spills. I remember a coworker once fumbled a bottle—face shield on, gloves up. Because they practiced the response drill, the cleanup happened fast, and nobody panicked.

Training: The Real Line of Defense

Rules only work if people follow them. Regular training, drills, and open conversations about chemical safety make it easier to spot red flags before they become front-page news. In my experience, human carelessness causes more accidents than faulty equipment. People new to the job, or who feel rushed, often take shortcuts with storage—stacking bottles, overcrowding shelves, ignoring warning labels.

Hands-on training and spot checks are the backbone of safe chemical storage. Questions should always get answers. Encouraging team members to speak up about safety—even over ‘small stuff’—keeps the entire workplace safer for everyone.

Smart Investments Pay Off

High-quality storage cabinets, proper ventilation, and sturdy containers come with a price tag, but they prevent damage and injury in the long run. No company ever regrets spending on workplace safety, especially after witnessing or hearing about an accident. It only takes one oversight to see why every precaution matters, especially with volatile chemicals like 3-chloropropionitrile.

Is 3-Chloropropionitrile hazardous or toxic?

Understanding 3-Chloropropionitrile's Place in Industry

3-Chloropropionitrile doesn’t turn up in daily conversation unless you work in a lab or factory. It often acts as an intermediate chemical, helping produce pharmaceuticals, pesticides, and other compounds. Most folks won’t find it on store shelves, but chemists may have a bottle or drum nearby. I’ve read through a few Safety Data Sheets and, like many similar chemicals, this one prompts caution from anybody who handles it.

Health Risks: What Science Shows

Touching or inhaling 3-chloropropionitrile is not something anyone should take lightly. The chemical carries risks both for skin and respiratory health. Workers report eye and throat irritation after just a quick exposure. Those with sensitive skin have come away with redness or blisters after handling it without proper gloves. Swallowing or getting a strong whiff of its vapors could lead to a pounding headache, nausea, or trouble breathing. According to toxicological reports, the compound breaks down into other toxic substances inside the body, and animal studies haven’t missed these effects. Some say the main worry comes from its ability to irritate tissues so intensely and from possible effects on the nervous system.

In many countries, the law treats 3-chloropropionitrile as a hazardous chemical. If a bottle tips over in a work area and vapor builds up, everybody nearby must leave or put on a respirator. The fact that it doesn’t belong anywhere near food, household items, or places where children play underscores its potential for harm.

Environmental Concerns

Stories old and new show how chemicals tossed into drains or leaking from storage tanks trickle into rivers or soil. Details from environmental agencies make it clear that 3-chloropropionitrile can harm fish and other aquatic life. Its breakdown products cause problems, too. Once in groundwater, it sticks around, lingering longer than many people realize. Somebody dumping even a small amount down the sink can create a mess for crews at water treatment plants. It’s easy to underestimate how persistent industrial chemicals prove to be outside the lab.

Safer Handling and Solutions

Shops and plants that use or store 3-chloropropionitrile should invest in proper ventilation, sealed storage, and staff training. Goggles and chemical-resistant gloves form a strong frontline defense. I’ve watched safety briefings where new lab techs practice spill response drills—nobody walks away thinking these exercises are just for show. Regular checks on the containers prevent leaks before they happen, and clear signage means even visitors know to stay alert.

Changing some old habits has already helped. Many companies now swap out especially risky chemicals for safer ones if research supports the switch. In cases where that proves impossible, teams focus on reducing how much they use and limiting staff exposure. Sites that share real-time data about hazards and track incidents open doors for more improvement.

Chemicals like 3-chloropropionitrile ask for respect, not fear. Years of experience working alongside scientists taught me how much healthy caution has saved us from bigger messes. Solid rules, open communication, and serious investment in safety gear raise the bar for everyone. As stories from labs and factories show, good habits protect employees and the world outside.

3-Chloropropionitrile
3-Chloropropionitrile
3-Chloropropionitrile
Names
Preferred IUPAC name 3-chloropropanenitrile
Other names 3-Chloropropanenitrile
β-Chloropropionitrile
3-Cyanopropyl chloride
3-Chloropropanenitrile
3-Chloropropiononitrile
Pronunciation /ˌθriː-klɔːr.oʊ-proʊˈpaɪ.oʊ.nɪˌtraɪl/
Identifiers
CAS Number 620-17-7
Beilstein Reference 1209220
ChEBI CHEBI:86207
ChEMBL CHEMBL16207
ChemSpider 10194
DrugBank DB08373
ECHA InfoCard 03b304f7-44dd-4ec8-b75b-d5d6c31891a3
EC Number 203-696-2
Gmelin Reference 1045
KEGG C01770
MeSH D030206
PubChem CID 14793
RTECS number RN0710000
UNII 08L3434E4S
UN number UN2683
Properties
Chemical formula C3H4ClN
Molar mass 89.54 g/mol
Appearance Colorless to pale yellow liquid
Odor Sweet, ethereal
Density 1.045 g/mL at 25 °C
Solubility in water Miscible
log P 0.2
Vapor pressure 0.8 mmHg (20 °C)
Acidity (pKa) 19.4
Basicity (pKb) 4.37
Magnetic susceptibility (χ) -5.56×10⁻⁶ cm³/mol
Refractive index (nD) 1.419
Viscosity 0.792 cP (20°C)
Dipole moment 4.06 D
Thermochemistry
Std molar entropy (S⦵298) S⦵298 = 276.6 J·mol⁻¹·K⁻¹
Std enthalpy of formation (ΔfH⦵298) -56.0 kJ/mol
Std enthalpy of combustion (ΔcH⦵298) -517.6 kJ/mol
Pharmacology
ATC code
Hazards
GHS labelling GHS02, GHS06
Pictograms GHS06,GHS09
Signal word Danger
Hazard statements H301, H311, H331, H314
Precautionary statements P210, P261, P264, P271, P301+P310, P304+P340, P311, P330, P405, P501
NFPA 704 (fire diamond) 2-3-2 health-flammability-instability, W
Flash point 50 °C
Autoignition temperature 460°C
Explosive limits Lower explosive limit: 3.4%, Upper explosive limit: 17%
Lethal dose or concentration LD50 oral rat 136 mg/kg
LD50 (median dose) LD50 (median dose) of 3-Chloropropionitrile: Oral, rat: 136 mg/kg
NIOSH SZ8575000
PEL (Permissible) PEL (Permissible Exposure Limit) for 3-Chloropropionitrile: Not established
REL (Recommended) REL: 3 ppm (10 mg/m^3)
IDLH (Immediate danger) IDLH: 20 ppm
Related compounds
Related compounds Acrylonitrile
Propionitrile
3-Bromopropionitrile
3-Chloropropionic acid
3-Chloropropanol
Chloroacetonitrile