L-(+)-threo-2-Amino-1-(4-nitrophenyl)-1,3-propanediol: An In-Depth Commentary

Historical Development

L-(+)-threo-2-Amino-1-(4-nitrophenyl)-1,3-propanediol carries a story rooted in decades of medicinal chemistry. Researchers during the mid-20th century searched through various amino alcohols, especially those bearing aromatic substitutions, in pursuit of novel antibiotics and selective biological tools. Efforts in post-war Europe and America often focused on derivatives of streptomycin and chloramphenicol, and compounds similar to this found their way into many investigational trials. Chemical syntheses evolved as bench-top chemistry gave way to the application of stereoselective methods in the 1980s. The capacity to separate enantiomers with high precision opened new possibilities for understanding structure-activity relationships.

Product Overview

Present as a crystalline solid, L-(+)-threo-2-Amino-1-(4-nitrophenyl)-1,3-propanediol demonstrates a well-defined molecular identity. Chemists and pharmaceutical scientists know the importance of single-enantiomer preparations to minimize side effects and enhance target specificity. This compound finds a place among potent chiral building blocks, sometimes referenced as a key fragment in the development of nitroaromatic drugs and specialty ligands. Not every molecule attracts researchers across multiple fields, but the features of this amino alcohol encourage repeated investigations—not only by synthetic chemists but also in the context of biological studies and analytical reference materials.

Physical & Chemical Properties

Users typically measure this compound as a yellow or light brown crystal, which owes its color to the aromatic nitro group. Its molecular weight sits at 212.18 g/mol, and it often appears as hygroscopic. That’s something to keep in mind—especially for storage under inert gas or in desiccators where water uptake could compromise purity. The compound dissolves readily in polar solvents like methanol and DMSO but struggles in typical organics such as hexane. Lab tests confirm a melting point range around 182–185°C. Such a profile helps identify the compound and separates it from similar amino diols lacking the nitrophenyl group.

Technical Specifications & Labeling

Suppliers opt for clear, robust labeling, listing not just the chemical name but also lot numbers and purity percentages (often quoted as >98%). Labels frequently display stereochemical descriptors for safety and regulatory needs. On technical sheets, potential contaminants like nitrate byproducts or residual solvents appear—a small yet vital detail for those invested in analytical chemistry. Purity checks use HPLC, NMR, and, less often, polarimetry. Chemists carefully note these specifications; contaminants and incorrect stereochemistry easily foul up pharmacological assays or scale-up syntheses.

Preparation Method

Labs primarily rely on a selective reduction protocol. Condensation of 4-nitrobenzaldehyde with nitromethane sets up a β-nitro alcohol intermediate, which survives subsequent reduction (e.g., with sodium borohydride or catalytic hydrogenation). The resulting 2-amino-1-(4-nitrophenyl)-1,3-propanediol is resolved using chiral acids or advanced chiral HPLC. Precise temperature control and careful monitoring prevent over-reduction or unwanted side reactions. Preparing this compound isn’t just rote benchwork—it takes exact timing to keep yields up and avoid contamination. Older patents and literature hint at more convoluted methods, but most modern labs stick to this streamlined process, always using batch records to trace product origins.

Chemical Reactions & Modifications

Its structure accommodates a range of modifications. Common transformations target the reduction of the nitro group to an amine, introducing valuable handles for peptide chemistry or further aromatic substitution. The diol portion reacts with acyl chlorides or sulfonyl groups, producing esters or sulfonates that serve as intermediates in more elaborate synthetic schemes. Chelators and bioconjugates sometimes start with this scaffold, exploiting the distinct reactivity of the chiral centers. The amino group lends itself to Schiff base formation or coupling chemistry, expanding the molecule’s utility to biotinylation or fluorescent tagging for research in protein labeling.

Synonyms & Product Names

Over the years, this compound has picked up an array of names: 4-Nitrophenylserinol, Threo-1-(4-nitrophenyl)-2-amino-1,3-propanediol, and L-threo-p-Nitrophenylserinol lead the pack. In pharmaceutical and biochemical catalogs, it sometimes goes by code names or catalog numbers, especially in those contexts where suppliers avoid lengthy IUPAC nomenclature. Careful attention to synonyms reduces ordering errors; having navigated research projects myself, mixing up enantiomers or accepting a racemic preparation leads to wasted time and budget.

Safety & Operational Standards

Handling nitroaromatic compounds carries well-documented risks—skin contact leads to irritation and accidental inhalation of dust impacts lab air quality. Good practice involves gloves, lab coats, and eye protection at all stages. Reference to Safety Data Sheets (SDS) often reveals whether specific spill management or disposal procedures differ from general organic waste. Facilities with fire or explosion guidelines pay attention to the oxidative properties of nitro groups, which occasionally exacerbate workplace incidents. Training remains central; even the most experienced chemist benefits from a culture that supports double-checking waste stream compatibility and segregating nitrated compounds from incompatible reactants.

Application Area

This molecule plays multiple roles in the broader context of drug discovery and biological research. Medicinal chemists value its chiral centers as templates for antibacterial, antiviral, and neuroactive drugs. Enzyme inhibitors have emerged from modifications at either the amino or hydroxyl groups, often demonstrating activity in preclinical cancer models or anti-inflammatory screens. Outside the pharmaceutical realm, materials scientists recognize the compound’s aromatic-nitro backbone as a starting point for specialty polymers and dyes. Analytical chemists employ it as a reference standard, capitalizing on its dense UV-Vis absorption for calibration and method development.

Research & Development

Ongoing studies track subtle tweaks to the parent structure, searching for analogs with improved water solubility or reduced toxicity. The field of antibiotic resistance constantly demands new scaffolds for lead generation, so chiral nitroarenes like this one still attract grant funding and collaborative efforts. Multidisciplinary teams—combining biologists and polymer chemists—see value in derivatizing both the amino and diol functionalities for applications in sensing, drug delivery, or even biomimetic catalysis. Regulatory trends, including increasing pressure to document every experimental gram, push for more robust traceability in sourcing and quality assurance.

Toxicity Research

Decades of pharmacological screening determined the compound’s nitro group plays a double-edged role: increasing reactivity but also raising cytotoxicity risks. Short-term exposures in animal models result in elevations of methemoglobin, and certain metabolic pathways convert the nitro group into mutagenic intermediates. High doses can depress central nervous system function, a property linked to both direct toxicity and impurities picked up in bad syntheses. Regulatory bodies, including the EPA and OSHA, keep a close watch on workplace use; published LD50 values guide permissible exposure levels. In my own work, I take risk management seriously, using flow hoods and consistent recordkeeping to avoid accidental overexposure or unsafe handling.

Future Prospects

Interest in chiral building blocks continues to rise, especially as green chemistry techniques grow more common. Advances in bio-orthogonal chemistry create new opportunities for molecules like this to serve as safer, more targeted probes in cell biology. Machine learning models feed on accumulated reaction data, offering predictive insights about functional group behavior and ease of synthesis. Streamlining the production chain encourages wider use—not just in drug screens but also in the search for immunomodulators or imaging agents. Sustainable practices, like solvent recycling, feature more in procurement discussions. The drive to minimize side effects pushes new analogs into early-phase human trials. As the research community renews its focus on both environmental safety and clinical promise, compounds with rich histories and versatile reactivity, like L-(+)-threo-2-Amino-1-(4-nitrophenyl)-1,3-propanediol, continue to hold their ground.



What is L-(+)-threo-2-Amino-1-(4-nitrophenyl)-1,3-propanediol used for?

Digging Into Its Story

L-(+)-threo-2-Amino-1-(4-nitrophenyl)-1,3-propanediol doesn’t exactly roll off the tongue, but this compound plays a much bigger role in medicine and science than its long name suggests. I first stumbled across it in an old pharmacology textbook. At that point, it was described as a chemical building block—part of the machinery that modern antibiotics and drug design rely on. Anyone who's dealt with stubborn infections might appreciate how hard scientists work to outsmart bacteria, and this compound helps lead the charge in that battle.

Roots in the Fight Against Infection

For folks who’ve wrestled with tough infections, the history of this compound should ring a bell. The molecule forms the backbone of chloramphenicol, an antibiotic launched into hospitals in the late 1940s. Chloramphenicol changed the way serious bacterial infections were treated, especially in places where other treatments fell short. Malaria, typhoid fever, and meningitis all bowed to its power. The 4-nitrophenyl part of the molecule paved the way for this antibiotic to disrupt bacterial protein synthesis, stopping the infection in its tracks.

Stories from hospitals paint a clear picture: before access to antibiotics like the ones this molecule helped create, simple infections often turned deadly. Now, fewer children die from infections like meningitis or typhoid. Many of us in developed countries might take that for granted, but even a fever could spell disaster just a century ago.

Lab Bench to Modern Medicine

Researchers don’t just see L-(+)-threo-2-Amino-1-(4-nitrophenyl)-1,3-propanediol as a curiosity. It serves as a critical template for synthesizing not only chloramphenicol but also other related drugs. Labs look for new ways to tweak this core structure—change a group here, swap a side chain there—in the hunt for antibiotics that dodge bacterial resistance. Recent data out of Asia and Africa show resistance rates to older antibiotics worsening year by year. If the base molecule didn't exist, the pipeline of experimental drugs would look much emptier.

As someone who’s followed global health for years, I’ve watched donated antibiotics save lives in rural clinics and refugee camps. Each shipment represents not just a box of pills but decades of chemistry and careful discovery work. The active ingredient owes its existence to the exotic backbone made possible by this compound.

Risks, Challenges, and a Path Forward

Of course, drugs built on this molecule aren’t perfect. Chloramphenicol, for one, comes with a risk of serious side effects if misused—anemia for one, sometimes fatal. Overprescribing or unsupervised use can magnify those dangers. The World Health Organization flags antibiotic stewardship as a pressing need, especially in overcrowded clinics.

Solutions don’t come easy, but education matters. Teaching patients why they can’t stop a prescribed antibiotic course midway. Training doctors to prescribe thoughtfully, not just for every sniffle. Supporting labs working to design safer alternatives using the same chemical backbone. Expanding access to diagnostics so the right drug gets prescribed for the right bug.

The Heartbeat of Modern Drug Discovery

Every time researchers return to L-(+)-threo-2-Amino-1-(4-nitrophenyl)-1,3-propanediol, they step into a legacy of curiosity and hard-earned progress. Its story reminds us that chemistry—at its best—protects lives, prevents suffering, and gives doctors another way to pull a patient back from the edge. That’s not just lab work; that’s hope in molecular form.

What is the molecular weight of L-(+)-threo-2-Amino-1-(4-nitrophenyl)-1,3-propanediol?

Chemistry’s Details Make a Big Difference

Every compound in chemistry carries a story in its structure, and that story tells how it interacts with everything else. L-(+)-threo-2-Amino-1-(4-nitrophenyl)-1,3-propanediol—quite a mouthful—packs multiple features into its name. It has an amino group, a propanediol backbone, and a nitrophenyl ring. Just seeing all those words, you start to realize there’s more going on here than just a collection of atoms stuck together.

In labs and factories, details like molecular weight steer everything from reaction planning to drug formulation. For anyone working in synthesis, dosing, or scale-up, the molecular weight isn’t a background number—it’s front and center, driving measurements, costs, and safety. This compound’s molecular formula is C9H12N2O4, giving it a calculated molecular weight of about 212.20 g/mol. That value didn’t just leap out of a reference book; it comes from adding up atomic weights to capture the exact makeup of the molecule.

Why the Number Matters in Real Work

I remember making mistakes in my early years in the lab. A decimal point in the wrong place could spoil days worth of work, wasting time and expensive reagents. Take this compound—miss the molecular weight and either your yield tanks or your reactants run out too soon. Pharmaceutical scientists could miscalculate dosing, which throws research into a tailspin and risks patient safety.

Drug development teams rely on precise weights to predict solubility, distribution, and even metabolic fate. At 212.20 g/mol, this molecule sits in a range that’s manageable for oral drugs. That fact affects more than academic conversation. Lower weights often make for better absorption, and that spills over into decisions about whether synthesis or chemical modification might improve performance.

In my work, tracking down errors in research often circles back to miscalculated molecular weights. A team in a research project can lose weeks because of overlooked decimals, especially when delving into new compounds with names even longer than this one. Reproducibility only happens when everyone uses solid numbers. Peers need the confidence that published studies describe reality, not rough estimates.

Solutions for Avoiding Calculation Errors

Chemists and pharmacists have tools now that just weren’t on the table decades ago. High-quality molecular weight calculators, digital lab management systems, and verified chemical databases stand guard against sloppy math. Still, the old advice holds—trust, but verify. Double-check with a periodic table before running a series of reactions. Write out the structure, add up the elements one at a time, and let someone else review the work, especially when planning anything on a larger scale.

Teaching young scientists isn’t only about building curiosity. Training includes respect for numbers and building habits to spot mistakes before they snowball. The best mentors I knew hammered home the trick—use technology, check by hand, talk through the logic. Relying only on software or databases opens the door for typos or copy-paste blunders. Sharing stories of real-world blunders, with all their awkward embarrassment, often drives the message deeper than a pile of dry formulas.

The Takeaway from Exactness

Accurate numbers mean something. For L-(+)-threo-2-Amino-1-(4-nitrophenyl)-1,3-propanediol, 212.20 g/mol reflects the little details that set apart reliable science from wasted effort. Solid numbers light the path through design, testing, and finally using these compounds in everything from research benches to real-world treatments. The calculation isn’t just a box on a worksheet—it’s the foundation for safe, trustworthy science.

What are the storage conditions for L-(+)-threo-2-Amino-1-(4-nitrophenyl)-1,3-propanediol?

Understanding the Basics

L-(+)-threo-2-Amino-1-(4-nitrophenyl)-1,3-propanediol, often recognized for its role as a chiral building block in various chemical syntheses, deserves thoughtful handling. Safeguarding any compound containing both an amino group and a nitrophenyl ring structure starts with honest assessment—not only of the chemical but the work environment itself. In my time around academic and industry labs, the difference between a locked cabinet beneath a leaky sink and a dedicated dry store couldn’t be clearer when a year-old batch changes color or forms crystals.

Why Temperature Control Makes a Real Difference

Temperature swings ruin more than just reactions. At room temperature, accidental spikes from sunlight or closeness to lab equipment risk degrading both amino and nitro components in this molecule. To keep its structure reliable, most guides point to a cool spot, ideally in the 2–8°C fridge range. I have seen samples stashed on a shelf at the back of a bench turn yellowish, hinting at slow oxidation and degradation. Reliable cold storage slows processes like hydrolysis and oxidative decomposition, protecting both the work and personal safety.

The Trouble With Moisture

Even trace humidity builds into big problems. Diols can soak up water from air, leading to unwanted hydrates or even hydrolysis. Once, a graduate colleague ignored warnings, left the jar half-open overnight, and ended up tossing out an entire batch after visible clumping and loss of performance in follow-up experiments. The lesson repeated: always keep this class of compounds in tightly sealed, air-proof containers. Desiccants tossed into secondary containers add extra confidence, especially in older storage rooms where ambient humidity is higher.

Avoid Exposure to Light and Oxygen

Light doesn’t forgive. A nitro group may sound stable, but excess sunlight or even harsh fluorescent bulbs nudge this molecule down pathways toward unwanted byproducts. Amber glass bottles, or even wrapping a clear vial in foil, shields sensitive compounds. Flushing with inert gases such as nitrogen or argon creates another layer of protection by keeping reactive oxygen away. I grew to appreciate the small habit of squeezing an argon-filled pipette bulb into the bottle headspace before sealing, especially after costly incidents of yellowed, useless compounds.

Labeling and Log Keeping

Mislabeling or forgetting the date pushes risks unnecessarily. Every new batch should go into storage with clear notes of the date and any storage anomalies noticed during use. More than once, a precisely kept log helped identify storage issues before entire research weeks spiraled. Reliable institutions often toss out compounds past their suggested shelf life, no matter how expensive, since failure in one experiment from degraded materials often wastes more time and money than a replacement order.

Finding Practical Solutions

Building better storage starts with honestly assessing available resources: refrigerators with lockable storage for chemicals, sealed desiccators for smaller samples, amber glassware, and routine audits. Fostering a culture of shared responsibility—one where everyone checks seals, labels, and refrigerant temperature—turns guidelines into practice. Sharing these realities with new lab members beats abstract protocols. No one forgets the lesson after watching months of synthesis efforts crumble because a bottle sat in the wrong place for too long.

Reliable Storage Supports Real Results

Every lab or storage room tells its own story, full of missed or seized opportunities. Protecting L-(+)-threo-2-Amino-1-(4-nitrophenyl)-1,3-propanediol with honest, direct storage habits not only rescues personal and financial investments but protects those handling it daily. Small investments—better bottles, clear logs, and a moment of vigilance—go further than any formal warning ever could.

Is L-(+)-threo-2-Amino-1-(4-nitrophenyl)-1,3-propanediol hazardous or toxic?

The Chemical at a Glance

L-(+)-threo-2-Amino-1-(4-nitrophenyl)-1,3-propanediol brings a long name and a complicated structure, but it plays a specialized role in chemistry labs and research. Folks in pharmaceutical and biochemical circles sometimes call it threo-p-nitrophenylserinol. Even a routine safety data sheet starts with warnings about toxicity. As a writer who's spent years tracking chemical debates, I know how fast online rumors spiral. Some call it outright dangerous, others say risks get hyped. So, straight talk: What should people really know?

Where the Worry Comes From

Look at the pieces. The “nitrophenyl” segment signals caution right away. Compounds with nitro groups often pose health hazards. Some find their way into explosives; others can damage red blood cells, cause methemoglobinemia, or irritate the lungs. Researchers track cases where dermal, oral, or inhalation exposure led to negative health effects. The diol backbone and amino acid motif make it a lot less volatile, but not harmless.

I’ve seen a few chemistry students wash down glassware without gloves and think, “No big deal.” That’s where trouble starts. Handling any aromatic nitro compound means wearing proper protection, period. The risk cuts deeper if you consider long-term impacts. Nitroaromatic chemicals sometimes behave as mutagens or cytotoxins. Occupational studies on chemicals with similar makeup hint at potential links to cancer, organ damage, or reproductive issues. The science isn’t always air-tight for every new variant, but patterns rarely break without reason.

Direct Toxicity and Known Hazards

Pure data doesn’t sugarcoat. Acute oral or dermal exposure can cause nausea, headaches, respiratory discomfort, skin rashes, or worse if dosage climbs. Most incidents don’t make the news — they end up in internal lab reports or obscure toxicology journals. Some government chemical safety databases say this compound’s metabolites sometimes form reactive intermediates that mess with cellular functions. I’d wager nobody wants to find that out the hard way.

Storage also stacks the risk. If the compound sits on a shelf, heat and direct light speed up decomposition. Because nitro groups increase fire sensitivity in some compounds, any accidental spill near an ignition source spells trouble. My own past work with similar nitrophenyl compounds always meant working under ventilation and keeping spill kits close by.

Pushing Safety Forward

Real-life improvements don’t rely on regulatory jargon. Good practices — universal in strong science environments — matter most. Proper gloves, eye protection, and lab coats deliver the first defense. Securing ventilation and using fume hoods dial exposure down. Leaving chemicals like this accessible in unlocked cabinets invites accidents. Clear labeling and in-house hazardous materials training keep new staff from learning lessons the hard way.

But accidents can’t meet silence. Reporting close calls and sharing best practices across labs help teams spot trouble before it snowballs. Manufacturers and catalogues can step up transparency with clear hazard documentation, not just brief footnotes about toxicity. Even at my most careful, the temptation to get lax hovers. But losing respect for nitrophenyl isn’t worth the price.

Thinking Beyond the Lab

Some argue small-batch or experimental chemicals get a pass on strict controls. Reality pushes against that. These compounds don’t leave their risk behind in the fume hood. Waste management, emergency response prep, and even transportation protocols build a culture of safety. Treating every unknown as a real risk—no matter how niche the project—keeps people and workplaces healthy. I’ve seen the difference: small habits shape big outcomes.

What is the chemical structure of L-(+)-threo-2-Amino-1-(4-nitrophenyl)-1,3-propanediol?

Chemistry Comes to Life

Every single day, chemistry puts its real face out there, shaping medicines, dyes, and even flavors. You don’t always stop and ask what specific molecules look like, but once you dig in, the world becomes a whole lot clearer. This is true for L-(+)-threo-2-Amino-1-(4-nitrophenyl)-1,3-propanediol. With a mouthful of a name, it comes up in discussions about organic synthesis, medicinal chemistry, and biochemical research.

Looking at the Details: The Structure

The structure isn’t just a series of random dots and dashes. This compound has a three-carbon chain at its core, with an amino group at the second carbon and hydroxyl groups hanging off the first and third carbons. The “L-(+)-threo” tag points to a specific tricks-of-the-light arrangement, or stereochemistry. Understanding stereochemistry in these contexts isn’t just a lab exercise. It often makes or breaks how a compound interacts with living systems.

What really grabs your eye is the 4-nitrophenyl group—an aromatic ring decorated with a nitro group at the fourth position. Chemically, this ring isn’t there just for show. The nitro group can seriously pull electrons through the ring, changing how the molecule reacts, and making it useful for both detection methods in laboratories and for therapeutic action.

Why Structure Matters in Real Life

The reason you care about a compound like this often comes down to what it does. In medicine and diagnostics, researchers have looked at this backbone as a building block for drugs that can interfere with disease processes, such as in antibiotics or agents that block neurotransmitter reuptake. The stereochemistry changes the way the molecule fits into the active site of enzymes or the pockets in proteins—kind of like a specialized Lego block.

Back in the lab, analyzing a molecule with both electron-rich (the amino and alcohol groups) and electron-poor (the nitro group) regions means you’re looking at something that can participate in a whole range of chemical reactions. Chemists exploit that push and pull between groups to build up even more complex molecules, sometimes using this compound as a stepping-stone in a longer synthesis pathway.

Facing the Challenges: Handling and Research

Recognizing the importance of structure goes beyond academic curiosity. If you’re working with a compound packed with both a sensitive nitro group and biological activity, safe lab practice becomes critical. Nitro groups, especially on aromatic systems, bring concerns about reactivity and environmental impact. Strict handling procedures and proper disposal go hand-in-hand with research progress to guard health and protect the planet.

Accurate determination of structure underpins safety, too. Analytical methods like NMR, IR spectroscopy, and X-ray crystallography don’t just check a box; they catch mistakes early, prevent costly or dangerous side reactions, and keep research reliable. If you overlook stereochemistry, you might wind up with a compound that acts in ways you didn’t expect—sometimes benign, sometimes hazardous.

Pushing Ahead: Better Practices and Smart Use

Harnessing the value of molecules like L-(+)-threo-2-Amino-1-(4-nitrophenyl)-1,3-propanediol starts with transparency. Full disclosure of structural data, handling protocols, and intended applications gives others confidence in your work, whether that's a regulatory body or a peer in the next lab over. Pushing for accessible, open-source information on organic compounds makes chemistry safer and faster for everyone. When people share not just the final product but the pathway and pitfalls they faced, they lift the whole field.

L-(+)-threo-2-Amino-1-(4-nitrophenyl)-1 3-propanediol