(1R,2S)-(-)-2-Amino-1-phenyl-1,3-propanediol: Building on Chemistry’s Progress

Historical Development

Chemists have often chased molecules that blend complexity and utility. (1R,2S)-(-)-2-Amino-1-phenyl-1,3-propanediol stands out in this context. Research rolled forward after scientists started investigating amino alcohols in the early half of the 20th century. Once people learned how to construct chiral building blocks reliably, interest sharpened in this compound’s structural relatives. Over decades, chemists dialed in the synthetic routes, and by the 1980s, methods gave better yields with tighter control on stereo-chemistry. As pharmaceutical companies searched for better beta-blockers, cold medicine, and synthetic intermediates, this molecule found steady demand. Laboratories saw it appear in advanced organic synthesis courses thanks to its accessible yet intricate skeleton. Not just a relic of organic chemistry textbooks, it now sits in catalogs worldwide, a testament to several generations' work.

Product Overview

(1R,2S)-(-)-2-Amino-1-phenyl-1,3-propanediol serves as a chiral amino alcohol, bridging pharmaceutical synthesis and academic research. Companies list it under several grades—each designed for specific downstream reactions or rigorous analytical work. Unlike its simpler cousins, this compound’s stereo-specific nature attracts those focused on asymmetric transformations. Researchers pick this molecule for its predictable reactivity and the toolbox it brings for drug discovery or specialty materials.

Physical & Chemical Properties

In its pure form, this compound appears as a white to off-white solid, crystalline to the naked eye, and faintly aromatic. Solubility reflects the amino and diol functionalities, bringing water, methanol, and ethanol into play while holding back in non-polar solvents. The melting point clocks in around 94-96°C, and the optical rotation, a key fingerprint for purity and chirality, settles near [α]D -40° (c=1, water). The molecular formula, C9H13NO2, tells a compact story: an amine and two alcohols orbiting a phenyl ring. Hydroxyl protons exchange quickly in D2O, familiar for NMR troubleshooting, but sample handling keeps things routine. I remember running a TLC and being struck by the clear spot and stubborn tailing if the silica gel contained water—those diols always love to drag a bit of moisture.

Technical Specifications & Labeling

Manufacturers ship this molecule in amber glass bottles, tightly sealed to protect against ambient moisture and light. Analytical sheets accompany each lot, reporting HPLC or GC purity (usually above 98%), enantiomeric excess (often >99% ee), and residual solvent levels. Labeling focuses on batch number, manufacturing date, storage guidance (2–8°C in desiccated storage), and an explicit warning about potential sensitization hazards. Proper hazard pictograms signal skin/eye irritation risks, and a Safety Data Sheet covers disposal and accidental exposure. I have found that clear labeling saves time in a fast-paced lab, particularly if a colleague stores it in the wrong section—this happens more than most admit.

Preparation Method

Most syntheses start with asymmetric reduction of substituted benzaldehyde derivatives. Chemists often use Sharpless aminohydroxylation for reliable regio- and stereocontrol. Protecting groups block one hydroxyl group while the amino group enters via substitution or reductive amination. Catalysts, such as osmium tetroxide or chiral auxiliaries, guide the outcome. Final steps involve deprotection, followed by purification over silica or crystallization from alcohol-water mixtures. Many small production sites stick with batch processes, keeping tight records for regulatory requirements. Over the years, I have weighed in at several benches, and the magic lies in keeping the reaction cold during addition—one slip, and side-reactions multiply.

Chemical Reactions & Modifications

Chemists love this molecule for its versatility. The diol can undergo selective protection for oligonucleotide synthesis or transformations toward glycoside mimics. The amino group can take on protective groups, acylation, or diazotization, feeding into more complex scaffolds. Chiral transfer hydrogenation finds tested ground here, as this backbone helps transfer stereochemistry into new bonds. Medicinal chemists like modifying the phenyl ring or elaborating one hydroxyl group to an ether, broadening molecular libraries with minimal synthetic overhead. A few years ago, a colleague leveraged this for an anti-viral cyclic ether—yield jumped by 15% after a small tweak to the phenyl ring substituent.

Synonyms & Product Names

Catalogs and literature reference this compound by a laundry list of names. Common synonyms include (-)-Norephedrine glycol, (R,S)-2-Amino-1-phenylpropane-1,3-diol, and (1R,2S)-Norephedrine diol. In drug-discovery applications, organizations sometimes list custom identifiers and internal numbers. Chemical suppliers tie it to registry numbers and CAS entries, with language differing by national regulations. Sometimes, a research group leans on abbreviations or internal acronyms—clarity in documentation always wins in the long run, especially when research moves between different labs or regulatory borders.

Safety & Operational Standards

The diol and amino functionalities prompt moderate hazard ratings, much like other small-molecule organics. Contact with skin or eyes causes irritation and, in rare cases, allergic responses. Single-digit up-take through dermal exposure stays relatively low, but inhalation of powders or dust should be avoided. Researchers follow standard BSL-1 precautions: nitrile gloves, goggles, lab coats, and operation under fume hoods if dust may form. Waste segregates into organic containers—never down the drain. I once watched a summer student try to clean a spill with bare hands and learned the value of reviewing safety briefings every lab meeting. Laboratory exposure limits reflect low chronic toxicity, but strict adherence to risk assessments keeps incidents rare.

Application Area

This compound serves as a workhorse in medicinal chemistry; beta-adrenergic antagonists, antihypertensives, and synthetic intermediates all feature modifications of this skeleton. Some teams use it in asymmetric catalysis while others push its use in polymers or chiral ligands. Cyclization or esterification unlocks fresh derivatives for biological screening. In academia, its predictable reactivity supports spectroscopy classes and organic synthesis teaching labs. Every semester, new students discover its utility in hands-on exercises, seeing pure theory translate into tangible results.

Research & Development

Research headlines spotlight its use as both a target and a tool compound. Scientists seeking new synthetic methods often pilot them with this amino alcohol, tracking stereocontrol and yield in challenging transformations. Pharmaceutical development leans hard into its beta-blocker legacy, while modern rounds of drug discovery exploit its robust skeleton for antiviral or anti-inflammatory leads. Some material scientists have explored its chiral influence in polymer backbones, finding subtle shifts in mechanical properties and spectroscopic fingerprints. Competitive industries press for greener and scalable preparation methods, including chemo-enzymatic synthesis and continuous flow processes, hoping to lower costs and reduce hazardous waste.

Toxicity Research

Toxicological studies show moderate oral and dermal LD50 values, consistent with low acute hazard but demanding caution. Chronic exposure data stay limited, and regulatory guidance urges prudent handling to minimize risk. Animal models point to potential CNS and cardiovascular impacts if misused, echoing findings for structurally related compounds. Ecotoxicity research flags possible risks in aquatic environments should disposal go unchecked. Regulatory agencies call for stringent record-keeping during scale-up and environmental monitoring near manufacturing sites. My own practice emphasizes double-checking PPE before tasks—a tiny deviation or short cut too often targets the hands, not just the data.

Future Prospects

Looking forward, chemists hope to fine-tune asymmetric routes for lower environmental impact and better atom economy. Interest grows in bio-catalysis for producing this molecule, as enzyme-driven processes cut energy use and waste. Drug discovery stays active, with structure-guided design using this building block to hunt for new therapies. Regulatory scrutiny increases, especially around manufacturing waste streams and safe scaling practices. Early-career scientists enter the field with green chemistry in mind, viewing each synthetic step through both a mechanistic and environmental lens. This molecule stands as a bridge—linking traditional organic chemistry and future-focused sustainable science.



What is (1R,2S)-(-)-2-Amino-1-phenyl-1,3-propanediol used for?

Unpacking the Substance’s Role

(1R,2S)-(-)-2-Amino-1-phenyl-1,3-propanediol stands out as a mouthful, but its role in the laboratory tells a simple story. This chiral building block pulls a lot of weight in pharmaceutical chemistry. I’ve come across it in discussions about the synthesis of beta-blockers, antidepressants, and some antiretrovirals. This specific stereochemistry isn’t just a technicality—choosing the right stereoisomer means getting the right biological activity in a drug, which can make the difference between medicine helping or causing side effects.

Why Stereochemistry Counts

Back in organic chemistry class, the first lesson that sticks is stereochemistry isn’t just a detail. Our bodies care about the shape of molecules, and the wrong configuration can make a drug ineffective or even dangerous. Thalidomide’s dark history reminds us that assuming all forms of a molecule are equal means putting trust in luck, not science. (1R,2S)-(-)-2-Amino-1-phenyl-1,3-propanediol brings an exact structure to the table, providing medicinal chemists a way to build target molecules with precision.

Real-World Impact of Chiral Amino Alcohols

I’ve spoken with colleagues at a local biotech company who use derivatives of this compound in the pursuit of new antimicrobial agents. Synthetic chemists lean on such intermediates because they simplify bringing new therapeutics to market. The process typically involves preparing these fine chemicals in controlled environments, aiming for purity and reliability, which keeps downstream products safe.

Chemists also use this compound in the enantioselective synthesis of various active pharmaceutical ingredients (APIs). According to recent academic articles, this approach enables generations of drugs with improved profiles for absorption, distribution, metabolism, and excretion. The result often translates to medicines that work better and produce fewer side effects, a win for both manufacturers and patients.

Challenges with Access and Quality

High quality doesn’t come cheap or easy. Purity standards push producers to go through multiple steps, each adding time, cost, and risk of contamination. Regulatory pressure grows every year as agencies like the FDA and EMA demand more transparency from supply chains. Companies cutting corners face real-world setbacks, from recalls to delayed approvals, directly hitting patient trust. It’s clear from industry data that investing in qualified suppliers makes sense in the long term.

Looking Ahead

Access to fine chemicals with defined stereochemistry supports future medical advances. But shortages, quality control issues, and patent holdings still create barriers. International cooperation among manufacturers, wider sharing of knowledge, and investment in greener, scalable synthetic methods could lower these barriers. Every incremental step puts better therapies in reach for more people.

Reliable chemical building blocks like (1R,2S)-(-)-2-Amino-1-phenyl-1,3-propanediol help researchers focus less on reinventing molecules and more on developing treatments that address real human needs.

What is the chemical structure and molecular formula of (1R,2S)-(-)-2-Amino-1-phenyl-1,3-propanediol?

Getting to the Essence of the Compound

There's something personal about breaking apart a molecule and seeing the framework inside. (1R,2S)-(-)-2-Amino-1-phenyl-1,3-propanediol stands tall in organic chemistry. The name might throw folks off, but each part tells a bit of the story.

This molecule’s backbone starts with propanediol—a three-carbon chain with two alcohol groups. Add a phenyl ring stuck on the first carbon, and an amino group on the second, and the picture sharpens. The (1R,2S) drags stereochemistry into the conversation, shaping the molecule’s three-dimensional life.

Chemical Structure and Formula

The molecular formula is C9H13NO2. Every formula helps sketch a mental map, but seeing the compound, either on a screen or drawn out in a lab notebook, makes the thing real. Take the first carbon: it binds to the phenyl ring, an alcohol (OH) group, and the rest of the chain. The second carbon takes on the amino group and a hydrogen, and the third closes things out with a terminal OH. 

Friends who draw molecules in a hurry know that orientation matters. The (1R,2S) label pins down the spatial arrangement. The R and S come from the Cahn-Ingold-Prelog rules, which sort out priorities around each chiral center. The (-) points to the molecule’s optical activity—a real concern in drug labs, where “left” can be medicine and “right” can be disaster.

Why Stereochemistry Makes a Difference

Most compounds in textbooks look flat, but in my experience, stereochemistry sits at the center of action in pharmaceuticals. The two chiral centers in this molecule offer possibilities for four stereoisomers, only some of which may work biologically as hoped. Chemists have watched mirror-image molecules from the same starting mix head off in completely different directions. This issue landed front and center in the history of thalidomide, and it hangs over every drug synthesis. 

Here, the (1R,2S) version brings only one arrangement. Change one chiral center, and the gears could grind differently in the body. Nature deals in stereochemistry without a thought, but manufacturing it takes time, resources, and some consistent checking.

Challenges and Solutions in Lab Work

Synthesizing compounds with two chiral centers consistently, without stray by-products, frustrates plenty of researchers. Selective methods like asymmetric synthesis come into play, using chiral catalysts or auxiliaries to nudge the reaction forward. Down the line, chromatographic separation steps whittle out isomers that missed the mark.

Checking purity used to be harder. Now, chiral HPLC and polarimetry sharpen the hunt. Reproducible methods lower the chance of mix-ups, and automation keeps things on track. For labs under pressure, these tools take hours off grunt work and help avoid costly recalls or clinical misfires.

Building on E-E-A-T Principles

People working in chemistry lean on solid evidence and methodical approaches. Every step has to make sense, and every claim about structure or purity must link back to real results—whether that means NMR spectra, X-ray crystallography, or validated synthesis routes. Tight documentation and peer-reviewed practices anchor trust, both in academic publications and for regulatory filings. Lapses bring risk.

In tackling (1R,2S)-(-)-2-Amino-1-phenyl-1,3-propanediol, blending hands-on experience with reliable scientific sources keeps standards high. Keeping training up to date, double-checking results, and sharing insights build a base that newcomers and veterans rely on every day.

How should (1R,2S)-(-)-2-Amino-1-phenyl-1,3-propanediol be stored?

Practical Concerns with Chemical Storage

Most folks working with chemicals know the worry that comes with storage. (1R,2S)-(-)-2-Amino-1-phenyl-1,3-propanediol doesn’t call attention to itself in the same way as something like hydrochloric acid, but it brings its own set of challenges. This compound serves as a chiral building block in drug synthesis. That alone means research teams and labs want to keep it reliable and pure.

Dangers of Moisture and Air

Exposing this molecule to the open air isn’t wise. Like other amino alcohols, it will soak up water from the air—what chemists call hygroscopic behavior. Even a little moisture can transform a free-flowing solid into a sticky mess and lead to breakdown over time. That’s wasted money, not to mention lost time for every failed reaction downstream. Most labs I’ve worked in keep a stash of desiccants—those little packs with "do not eat" warnings—right inside the bottle to draw out any stray humidity. A tightly sealed amber glass container stops more than just evaporation; it also blocks out light that could slowly trigger unwanted changes.

Temperature and Light: Friends or Foes?

Nobody wins storing this amino alcohol anywhere near a heat source or sunny window. Many organic compounds, including this one, degrade or racemize faster with heat or UV exposure. Chiral purity can drift; that’s a headache for anyone chasing a single enantiomer’s unique effects. I’ve kept sensitive chemicals like this in standard lab refrigerators. Temperatures around 2–8°C work well—cold enough to slow breakdown, but not so low as to risk condensation when opening the bottle. Regular freezer cycles may introduce water vapor, so a cold, dry fridge is safest.

Labeling and Inventory

The more you work in shared spaces, the more you notice mistakes multiply. Labeling the bottle with the opening date isn’t just bureaucracy—this practice gives a clear record of an item’s shelf life in real conditions. Always note storage temperature and any peculiar observations (change of color, solid formation) right on the label. I’ve learned to trust handwritten notes over memory; those scribbles often rescue you after a week in a hectic lab.

Handling and Safety

Gloves, goggles, and fume hoods are basic habits. It’s tempting to relax with solids, but this one can irritate skin and eyes. My own carelessness once left me with a rash that stuck around longer than I’d like to admit. Keep transfers quick, minimize bottle opening, and always clean up spills right away—no one benefits from playing chemist with a contaminated benchtop.

Disposal and Responsible Use

Nobody profits from leftover material lingering forever at the back of a shelf. Check local regulations for the best disposal route; unused or spoiled amino alcohol often belongs in a specialized waste container. Over the years, I’ve watched labs get dinged by inspectors for forgotten chemicals with faded labels. Regular audits clear out hazards and keep spaces safe for everyone.

Why It Matters

At the end of the day, keeping (1R,2S)-(-)-2-Amino-1-phenyl-1,3-propanediol safe boils down to protecting people, budgets, and research. Smart storage prevents loss and avoids risks. Good organization and dry, cool, sealed storage let this compound live up to its promise on the bench, not as an expensive puddle in the trash.

Is (1R,2S)-(-)-2-Amino-1-phenyl-1,3-propanediol available in different purities or grades?

More Than One Grade on the Shelf

Not every bottle in the lab claims the same badge of purity. I've seen (1R,2S)-(-)-2-Amino-1-phenyl-1,3-propanediol pop up in a few catalogues, and labs often face a puzzling menu of purities. One supplier offers an “analytical grade”—well over 98%. Another lists “technical grade” material that drops several points on the purity scale and carries the scars of other compounds from synthesis. What lands at your bench depends a lot on the job at hand and the budget set by the person holding the purse.

Why Purity Ranges Shape the Work

Years ago, I watched a colleague struggle through a chemical reaction that spun off erratic results. Turned out the culprit was a cheap, less pure batch of amino-phenyl-propanediol. Even fractions of a percent difference in purity changed the outcome, sometimes swapping a clean reaction for a sticky, troublesome mess.

Pharmaceutical groups ask for the cleanest stuff. Their chemists demand material tested for residual solvents, heavy metals, and chiral purity. That last piece—chirality—calls for extra attention, especially since this molecule’s activity hangs on the correct mirror image. A batch with poor enantiomeric excess means researchers or manufacturers can end up with the wrong activity in a drug or diagnostic. So, high-purity, enantiomerically pure grades aren’t just nice—they’re non-negotiable in that world.

Cost Versus Confidence

In a university, money often runs thin, so technical grade gets picked because it leaves a few coins for other projects. Analytical labs, though, can’t tolerate mystery peaks in their chromatograms. They pay for purer material so they can trust their data.

Manufacturing adds another twist. A kilogram-scale run probably won’t blink at a few tenths of a percent impurity if the downstream steps clean it up. On the flip side, an impurity that sneaks through could spoil an entire lot. Nobody wants to call customers and admit a recall because the starting material let them down.

Quality Control Makes or Breaks the Batch

GMP (Good Manufacturing Practice) means there’s a mountain of paperwork behind every gram. Chemists measure purity again and again. Reputable suppliers throw in certificates of analysis and even third-party testing reports. Those steps help buyers sleep better—especially if their end product will reach people.

Room for Sloppiness Shrinks in Modern Science

Mistakes and contamination make headlines. That scares many folks who work with fine chemicals. With stricter audits and more rigorous traceability, chemists now double-check supplier qualifications. Word spreads quickly if a supplier offers inconsistent grades or mislabels a batch. Sometimes, labs go as far as running extra in-house tests after delivery, just to make sure the label tells the truth.

Raising the Bar: What Would Help

Public databases with transparent sourcing and real-world test data could chip away at uncertainty. If buyers had access to crowdsourced reports—direct feedback from working chemists—confidence in the supply chain would climb. Tighter collaboration between suppliers and users, along with clear standards for different purity grades, might save labs from costly reruns and failed syntheses.

Better clarity about what each grade means—a universal language, not just marketing talk—should let scientists and manufacturers make choices without rolling the dice on quality. No more cross-checking a dozen spec sheets or wondering if this lot will stall the next trial run.

What are the safety precautions and handling instructions for (1R,2S)-(-)-2-Amino-1-phenyl-1,3-propanediol?

Respecting What’s on the Lab Bench

My early days in the lab taught me one thing – never underestimate a chemical you’ve just met. This approach matters especially when working with instances like (1R,2S)-(-)-2-Amino-1-phenyl-1,3-propanediol. Few people outside a chemistry lab will recognize this compound, but its safety demands attention and a healthy respect.

Health Risks: What the Data Shows

Chemicals that contain an amine group and aromatic ring often cause irritation. Skin, eyes, and respiratory tract line up as easy targets if exposed. Toxicological studies point to symptoms such as coughing, sneezing, and skin redness. The phenyl component can lead to central nervous system effects if mishandled, based on comparable compounds reported in regulatory databases. My hands still remember a careless splash from a similar compound – not serious, but a good reminder.

Protective Gear Saves More Than Just Clothes

Putting on the right gloves – usually nitrile – and a lab coat makes a difference. While goggles can fog up, they beat squinting away splashes. Fume hoods matter most, especially during weighing or transfers, since dust or vapors remain unpredictable. A friend’s story about a minor reaction gone wrong inside a closed room shows the value of proper ventilation – open space cuts danger fast.

Storage Means More Than a Label

Labeling stays essential, but storage needs real attention. (1R,2S)-(-)-2-Amino-1-phenyl-1,3-propanediol does best away from light and strong oxidizers. I’ve seen bad things happen when dust from one bench mingles with incompatible substances. Keep containers tightly closed and use secondary containment. Spills happen more often near shared storage, so good practice always includes a set-aside space on a dedicated shelf.

Spills and Disposal: No Room for Shortcuts

Spills bring instant pressure. The correct way means wiping up small quantities with absorbent pads, using gloves, and keeping splash danger down by moving slowly. For larger quantities, the right call means reaching for a spill kit rather than improvising. Disposal follows the school’s hazardous waste stream, never the drain—even trace amounts count for a lot, since regulatory fines and lab safety violations can land on a supervisor’s desk.

Training: The Overlooked Component

Lab safety takes more than posters and binders. Training—actual hands-on experience—teaches judgment in a way reading can’t. Watching a more experienced chemist neutralize a small leak stuck with me more clearly than a stack of safety data sheets. Practical drills on chemical intake and emergency response help everyone breathe easier.

Potential Solutions and Best Practices

Real change follows a few practical steps. Keep safety data sheets within reach, but also review them regularly. Institute routine checks of ventilation and protective equipment. Avoid working alone with new reagents—another set of eyes can catch a forgotten cap or loose glove. Push for a culture where reporting spills or mistakes is normal, since silent labs can turn small problems worse. Clear messaging, continual training, and hyper-awareness in the lab cut risk to a minimum, and protect everyone who works with potentially hazardous materials like (1R,2S)-(-)-2-Amino-1-phenyl-1,3-propanediol.

(1R 2S)-(-)-2-Amino-1-phenyl-1 3-propanediol