Tetradecanethiol: A Down-to-Earth Look at a Classic Organosulfur Compound
Historical Development
Chemists have tinkered with alkanethiols since the early 20th century, but tetradecanethiol, sometimes known as 1-tetradecanethiol or myristyl mercaptan, left its mark on the story of organic synthesis in the decades following World War II. The post-war surge in industrial chemistry threw a spotlight on thiols, triggering research into their properties, odorous nature, and their knack for binding to metals. I remember reading how French and British researchers in the 1950s were fascinated by long-chain thiols for their potential as lubricants and corrosion inhibitors. Eventually, industries discovered that tetradecanethiol offered just the right balance of a manageable odor, high hydrophobicity, and surface activity, pushing it further into applied research.
Product Overview
Tetradecanethiol steps onto the scene as a clear, oily liquid with a distinct, sharp smell often associated with its sulfur atom. Its role counterbalances glamour with practicality. You find it in surface chemistry, self-assembled monolayers, and sometimes lurking in the corners of advanced nanotechnology labs. Every batch of tetradecanethiol lands with a promise: high purity, consistent performance, and a reputation earned through decades of chemical service. Sitting between familiar short-chain and more unwieldy longer-chain thiols, it brings a clean C-14 backbone together with that reactive thiol group.
Physical & Chemical Properties
With a molecular formula of C14H30S and a molar mass near 230.45 g/mol, tetradecanethiol won’t evaporate away like an alcohol or lighter thiol. It holds a boiling point around 314°C, which keeps it stable during many standard chemical treatments. The melting point sits close to 22°C, which can make it a solid on a cold bench and a viscous liquid in a warm hand. Its density clusters around 0.857 g/cm³, and its refractive index marks it as an organic, non-polar substance. Its famous, sometimes pungent, odor isn’t just an inconvenience for the nose; it’s a built-in safety signal reminding you of its reactive edge. Solubility in non-polar solvents stands high, but water won’t dissolve it—a trait that drives most of its practical uses.
Technical Specifications & Labeling
Producers stamp labels carrying purity figures that often read 98% or higher—sometimes called technical or reagent-grade. Important technical specs like acid value, moisture content, and the percentage of disulfide impurities guide purchasing decisions. Proper storage instructions include amber bottles to block light and tight seals to fight oxidation. The Safety Data Sheet (SDS) sets expectations straight, covering hazards and safe handling without sugarcoating. You’ll see hazard pictograms, GHS warning statements, and first-aid instructions printed right alongside instructions for use. Each batch’s certificate of analysis tracks batch number, purity, and sometimes even the metal content, useful if your laboratory demands know exactly what you’re working with.
Preparation Method
Synthesis of tetradecanethiol in the lab often involves old-school organic reactions, such as treating tetradecyl halides with thiourea followed by basic hydrolysis. Industrial settings reach for routes that minimize byproducts, using sodium hydrosulfide with tetradecyl chloride, or even reducing tetradecyl disulfide. The chemistry here reminds me of those long days in graduate labs, as a simple alkyl halide meets thiourea and emerges, after a few steps, with the characteristic thiol funk. Quality control during production keeps an eye on color (it should be nearly colorless), sulfide impurities, and the tell-tale presence of higher alkanethiols that can ruin downstream applications.
Chemical Reactions & Modifications
Tetradecanethiol turns into a workhorse in surface modification, latching onto gold, silver, or even quantum dot surfaces to form monolayers. The S–H bond reacts with metal surfaces, capping nanoparticles or building hydrophobic barriers. I’ve run coupling reactions in college, using tetradecanethiol as a chain transfer agent in radical polymerizations—an unsung but essential role. Oxidation remains one pitfall: thiols can dimerize to form disulfides, sometimes by accident on the benchtop. Chemists often tweak the tail end with functional groups, letting it interact with different environments or materials, pushing its role far beyond a simple reactive compound into sensors, biosurfaces, and smart coatings.
Synonyms & Product Names
Tetradecanethiol lurks under several names—1-tetradecanethiol, myristyl mercaptan, and n-tetradecyl mercaptan. Chemical catalogs encode it as CAS 112-71-0. Depending on the supplier, you might see branding under these functional synonyms, with terms like myristyl thiol or simply C14-thiol showing up in product sheets. This proliferation of names sometimes frustrates new buyers but also speaks to its reach across different scientific communities—material science, organic chemistry, and even the odd biochemistry application.
Safety & Operational Standards
Responsible labs treat tetradecanethiol with respect. Contact with skin or inhalation of vapors brings real health risks: headaches, nausea, irritation, and more serious central nervous system symptoms with hefty exposure. Ventilation and a solid fume hood make all the difference, along with nitrile gloves, safety goggles, and lab coats. Its strong odor serves as an easy warning of leaks, but don’t rely on your nose once you smell nothing—it’s easy to build up toxicity over time in poorly ventilated spaces. Spills call for swift action with absorbent material and disposal in line with hazardous waste procedures. OSHA and GHS standards spell out storage away from oxidizers or acids, keeping bottles shut tight to slow down degradation. Fire risk is genuine as for most organosulfur compounds, so keep flames at bay.
Application Area
Surface chemistry reigns as the main playground for tetradecanethiol—think of gold surfaces in electronics or sensitive biosensors. Long-chain thiols like this one let researchers build robust self-assembled monolayers, layering molecular structures atom-level thick. I’ve watched colleagues shape robust hydrophobic coatings or direct the assembly of nanomaterials, tuning properties with nothing but a judicious soak in thiol solution. Lubricant additives, corrosion inhibitors, and flotation agents in mining still owe a debt to compounds like tetradecanethiol, showing that its value stretches across basic research and heavy industry. Lately, the move into quantum dot modification hints at its next boundary, impacting photonics and even diagnostic tools.
Research & Development
Research groups around the globe won’t let tetradecanethiol gather dust. Surface science journals burst with every new twist on monolayer assembly or gold nanoparticle functionalization. Nanoscience circles talk up the balance between chain length and stability, noting how C14 finds a sweet spot between flexibility and surface packing. In photonics, scientists layer tetradecanethiol onto semiconductor dots, controlling fluorescence or solubility. Laboratory notebooks fill with the details: reaction time, purity, chain length comparisons, and the effect on final product performance. Funding agencies keep supporting new platforms for sensing, catalysis, and advanced manufacturing, so this venerable thiol remains central in cutting-edge R&D.
Toxicity Research
My first introduction to the toxicity of organosulfur compounds came from a lengthy lecture and a handful of grim case studies from the 1970s. Tetradecanethiol doesn’t escape toxicity concerns, though it’s less volatile and arguably less acutely noxious than its lighter cousins. In vivo and in vitro studies point out moderate oral toxicity in animals, with dermal exposure producing local irritation. Chronic effects seem mild in well-ventilated workspaces, but improper handling builds up over time, leading to cumulative burdens on the liver and central nervous systems. Research continues, driven by the ongoing need for new toxicity profiling and better personal protective measures. Industry regulations force routine reviews of exposure limits, storage practices, and medical monitoring—no room for slack discipline here.
Future Prospects
Looking ahead, tetradecanethiol isn’t going anywhere. Growing demand for greener electronics, sustainable sensor coatings, and smart materials promises a steady drumbeat of research. Some current work explores bio-based synthesis routes, reducing waste and sidestepping the worst sulfur odors. Meanwhile, the marriage of nanotechnology with biological environments opens fresh fields for C14 thiol—think advanced drug delivery, smart surface engineering, or viral detection platforms. Universities and startups keep investing in processes that lower toxicity, boost recyclability, and refine performance. The future looks like a gradual shift toward safer production, environmentally mindful protocols, and ever-smarter applications—carrying tetradecanethiol’s legacy into new scientific frontiers.
Where Tetradecanethiol Fits In
Tetradecanethiol doesn’t pull headlines like some of the chemicals that stir up health or environmental debates. Yet, people in science labs and tech companies use it for things that matter to our daily lives in more ways than most folks realize. As a working chemist, I’ve come across this compound often during surface science projects and nanotechnology experiments.
Building Nanoscale Surfaces
The gold world loves tetradecanethiol, especially for crafting self-assembled monolayers (SAMs). In simple terms, it sticks tightly to gold like Velcro, letting scientists line up molecules in neat, dense rows. This matters for the electronics in our devices. For instance, tuning how gold surfaces behave helps create tinier, more efficient sensors and memory chips. Labs around the world use tetradecanethiol to customize gold sensors for everything from glucose test strips to next-generation environmental detectors. Those who work in the cleanrooms fine-tune surfaces by using this molecule because its sulfur end grabs onto gold atoms, while its chain tail points out, changing how the gold interacts with air or liquids.
Molecular “Paint” for Research
During my time in research, tetradecanethiol has been a go-to pick for making non-stick coatings on experimental chips. Unlike Teflon pans, these coatings don’t flake off or burn up. Instead, they keep proteins, cells, and dirt from glomming onto tiny structures where you want to study just one reaction at a time. In biosensor development, this sort of control can make an unreliable test much sharper. Students in undergraduate labs often run into it in surface chemistry modules—learning firsthand how molecular design changes performance in real-world devices.
Fine Tuning Nanomaterials
As electronics push into the nanoscale, researchers need tools to control just how small structures grow and how they interact with the world. Tetradecanethiol can cap tiny gold or silver particles, keeping them the right size and keeping them from clumping. The end result? Consistent nanoparticles for imaging cancer, making smarter drug delivery vehicles, or improving catalytic converters in vehicles. Without this molecular control, many “wonder material” breakthroughs stall or never make it past prototypes.
Looking Out for Safety and the Future
Tetradecanethiol brings clear benefits, though it reminds us how easily a valuable tool can present risks if misused. Skin contact creates problems—dermatitis and allergic reactions pop up if proper gloves don’t come out of the drawer. It doesn’t break down easily in nature, so waste handling plays a central role in any lab that uses it. Manufacturing sectors and academic research groups have pushed toward better containment and disposal, reusing solvents, and using closed systems to keep both workers and the surrounding environment safe.
New Frontiers and Responsible Use
Those who design electronics, sensors, and medical devices will likely keep tetradecanethiol in their toolbox. As people demand faster, smaller, and safer tech, the details at the molecular level start to matter more. Whether tuning protein arrays for rapid testing or controlling nanoparticle growth, this long-chain thiol stays relevant. Maybe one day, we’ll swap it out for something that breaks down easily in nature—green chemistry is picking up steam, especially in the materials world. Until then, careful handling and respect for its role in innovation help keep both progress and people on the right track.
Tetradecanethiol's Place in Science and Industry
Ask any chemist about tetradecanethiol, and you’ll probably hear “C14H30S.” This simple formula stands for a long-chain molecule with fourteen carbons, thirty hydrogens, and a sulfur atom at one end—that’s the thiol group. This isn’t just a random assembly of atoms. This particular arrangement creates a chemical with greasy texture and distinct smell, showing up everywhere from research labs to manufacturing floors.
How Tetradecanethiol Interacts with Surfaces
In my time working with thin films and nanotechnology, tetradecanethiol often acted as a friendly gatekeeper. Add a little to a clean gold surface, and you see an organized layer form, almost like the shingles on a roof. Scientists call this a self-assembled monolayer. In research, these monolayers help build sensors, test new materials for electronics, and protect surfaces from corrosion. The discovery that you can turn a bare metal into a tailored surface just by dipping it in a solution comes across as impressive every single time.
Why Knowing the Formula Matters
If you ever mixed up chemicals or calculated how much you need to weigh out, you’d know every atom counts. Tetradecanethiol’s C14H30S tells researchers exactly how it will react and what you should expect in experiments. Take gold nanoparticles, for example. Too short of a chain, and you won’t get stability. Too long, and aggregation can botch your results. The fourteen-carbon chain helps strike the balance between good coverage and workable solubility.
Beyond the Bench: Potential Health and Environmental Concerns
Tetradecanethiol brings value, but it isn’t free from concern. Anyone who’s used thiols knows the rotten egg smell isn’t just unpleasant; it can signal health hazards. Prolonged skin contact or inhalation leads to irritation, so lab workers stick with fume hoods and gloves. Spills need immediate cleanup, or you’ll hear from the whole floor. Because it’s not highly volatile, the risk of inhalation stays low, but education on safe handling remains key.
Minding the Details: Responsible Use and Solutions
On the environmental side, disposal and containment matter. Tetradecanethiol doesn’t dissolve well in water, and persistence in the environment could spell trouble for aquatic life. Facilities need to treat their waste, not just dump it down the drain. That pushes companies and labs to build better filtration and neutralization systems. Education can’t take a back seat—a quick safety video or reminder goes a long way. Sharing knowledge about proper storage keeps labs running safely and prevents unwanted reactions.
Final Thoughts: Staying Informed Means Staying Safe
The chemical formula C14H30S might not seem like much to most, but it opens the door to big opportunities and responsibilities. From building sensors to keeping water clean, knowledge about tetradecanethiol and its proper use makes all the difference. People working with it need to pay attention to both safety and impact, leaning on facts and not just convenience. It all starts by knowing—inside and out—the full meaning behind a straightforward string of letters and numbers.
What We Know about Tetradecanethiol
Tetradecanethiol sounds like something you’d only run into in a research lab, but folks who work with chemistry, specialty coatings, or electronics often see it on a regular basis. The compound has a long, waxy chain and a sulfur-containing group. Its structure gives it the power to bond to metal surfaces, so people use it to build up protective coatings or customize nanoparticles. That odd sulfur smell, sometimes compared to rotten cabbage or garlic, makes it hard to forget after the first encounter.
Is There Real Danger Working with Tetradecanethiol?
Safety questions matter a lot in any lab or industrial setting. Checking real-world safety data, I noticed that tetradecanethiol can cause trouble. Skin and eyes take the brunt of the hit—direct contact can trigger irritation, redness, and even burns with enough exposure. Inhaling the vapors might leave you coughing or feeling lightheaded. Its low volatility keeps the air problems down compared to more aggressive chemicals, but spills or high-heat operations change that quickly.
Swallowing this stuff makes a bad day even worse. Studies published by companies and regulatory bodies point to toxicity if ingested or absorbed in larger amounts. For folks working with it daily, that prompts goggles, gloves, and proper ventilation every single time—the old “better safe than sorry” advice shows up for good reason.
Environmental Impact and Exposure Concerns
Most thio-compounds bring extra baggage for the environment. Tetradecanethiol, thanks to its sulfur group, doesn’t break down as easily as some simple organics. Its oily nature helps it hang around in soil or water, and that persistence carries risk for aquatic life. Fish and smaller creatures suffer disruption to their respiratory systems or cell membranes if the compound builds up in waterways. Even though it rarely gets dumped in huge quantities, any sloppiness in disposal can mean long-term contamination issues.
Looking at workplace exposure, there’s not a mountain of government regulation on tetradecanethiol itself. Instead, it slips under broad rules covering thio-alcohols and organic sulfur compounds. The lack of specific standards makes training, monitoring, and careful storage extra important. From my lab days, I remember every container carried strong warnings, and the clean-up protocols doubled up whenever any of these longer-chain thiols were in use.
Managing the Risk and Staying Safe
Hazard doesn’t always equal danger—for most people, the real risk stays low as long as good practices run the show. That means always using chemical splash goggles, working with gloves (nitrile ones last longer against these oily compounds), and handling the material in a well-ventilated space. Fume hoods aren’t glamorous, but they’ve saved a lot of lab coats from disaster.
Waste collection comes next. Sending anything with a sulfur tail to general sewage or landfill causes headaches for water treatment plants and local wildlife. Specialized disposal makes a difference, even if it seems like overkill for tiny quantities. For organizations that use lots of tetradecanethiol, spill kits, routine safety training, and an emergency plan never go out of style.
Anyone thinking about using or working with tetradecanethiol owes it to themselves—and those downstream in the environment—to respect its risks. The hazards might not jump out compared to some heavier hitters in industry, but they’re enough to demand thoughtful safety habits and smart disposal at every step.
Why Storage Matters More Than Most Think
Sitting in a lab with the sharp, unmistakable odor of thiols lingering in the air, proper storage of tetradecanethiol becomes an issue that goes beyond just lab protocol. Having worked with noxious and sensitive compounds for years, I’ve seen firsthand how improper storage leads to costly waste and even puts people at risk. Tetradecanethiol, with its long hydrocarbon chain and reactivity, often turns up in both advanced research and industrial synthesis. Yet despite the fancy fume hoods and plastic gloves, many overlook the basics — keep moisture and air away, prevent accidental spills, and avoid contamination at all costs.
Understanding Its Behavior: Not Just Another Liquid
On the shelf, tetradecanethiol looks tame, but the compound has a hidden reputation. It releases sulfurous vapors, and a leaky container can turn a storeroom into a hazardous zone. Exposure to oxygen can lead to gradual oxidation, which not only ruins the chemical’s quality but can also form unpleasant byproducts. Even trace moisture can encourage slow decomposition. At room temperature, its volatility might seem manageable compared to shorter-chain thiols, but anyone who has ever dealt with the smell knows it finds a way to linger. Long-term storage amplifies every little mistake, turning routine carelessness into a full-on headache for lab techs and safety teams.
Best Practices Backed by Experience
From day one, every bottle should stay tightly closed. Glass containers beat plastic hands down; the latter often allows trace vapor loss, and over time, that shows up as both a foul odor and lower purity. I always label with clear dates and hazard warnings — confusion or faded writing invites accidents. Even in secure spaces, store it in a dedicated chemical cabinet, away from acids, oxidizers, and especially away from any food or personal items. Some colleagues keep the chemical under a layer of inert gas like nitrogen; this pays off for samples that must stay pristine for months or years.
Flammable liquid storage rules apply: cool, dark, out of the sunlight. A metal flammables cabinet works best. Don’t overlook the small things: absorbent spill pads under containers, reliable drip trays, and regular checks for leaks. It’s too easy to store it on a back shelf, forget about it, and pull out a bottle that’s half-emptied itself into the cabinet, creating both loss and mess.
The Human Impact: Training and Accountability
Labs run on trust and attention to detail. Every mistake puts someone else at risk, especially if newcomers aren’t trained to recognize the corrosive and toxic nature of thiols. Regular reviews, clear written procedures, and hands-on demonstrations help everyone understand what’s at stake. I’ve seen the best results in teams where people report problems right away, not just bury them. More oversight from lab managers does help, but fostering a culture where safety matters to everyone pays off more in the long run.
Looking Ahead: Investing in Better Solutions
As research scales up, more chemicals like tetradecanethiol turn up in shared stockrooms. The industry now offers improved seals, chemical-resistant coatings for bottles, and even leak-proof transport containers. Installing automated monitoring for storage room air quality helps catch leaks early. Investing in these tools costs less than a cleanup or hospital bill. In my own lab, a few hundred dollars spent on high-quality storage gear and training paid back in peace of mind and uninterrupted research. Safety never happens by accident—consistent effort keeps both people and chemicals in the best shape possible.
Everyday Impact in Surface Chemistry
Tetradecanethiol doesn’t usually make headlines, but anyone who has ever worked in a surface chemistry lab probably knows that strong, reliable monolayers don’t magically appear with water and soap. Tetradecanethiol brings a long hydrocarbon chain and a sulfur head together, making it a regular choice for forming self-assembled monolayers (SAMs) on gold surfaces. Gold has a habit of attracting sulfur atoms, so labs often use tetradecanethiol to create tightly packed, hydrophobic coatings. With these in place, research on biosensors, electrodes, and even designed nano-devices moves forward. Without these coatings, experimental data often falls apart due to contamination or erratic surface effects. I’ve seen plenty of test results turn from inconsistent to crisp after a proper SAM layer goes down.
Friend of the Nanoparticle Synthesizer
Managing nanoparticles takes more than just tossing metals in some solution and hoping for the best. Stability is a constant battle. Tetradecanethiol steps into nanoparticle syntheses, especially with gold or silver, by sticking to surfaces and stopping the tiny bits from clumping together. This capping keeps particle size under control and preserves purity, which makes characterization and downstream use much easier. Several years back, while working on nanorods for a solar energy pilot, we scaled production up and watched it all fall apart until a simple tweak—switching to tetradecanethiol as a stabilizer—brought repeatability and reliable dispersions.
Electronics and Flexible Devices
In the world of soft electronics, organosulfur compounds like tetradecanethiol often show up in the production line. Researchers rely on its ability to tune wetting and adhesion between organic and metal parts. Flexible circuits and display prototypes stick together better with a thin, hydrophobic SAM, which also guards against oxidation. Applying these functional coatings keeps expensive metals active and protected. Without this added stability, a lot of flexible electronics break down after a few rounds of bending and environmental exposure. I watched a team rescue hours of device fabrication by tweaking substrate conditions with a tetradecanethiol pretreatment—it’s the type of practical chemistry that saves budgets and careers.
Material Science and Lubrication
Material scientists often look for ways to reduce friction on intricate mechanical systems. A lot of research shows that alkane thiols form slippery surfaces, and tetradecanethiol hits a sweet spot—not too short, not too long, just enough to make a measurable difference. It finds a place on microelectromechanical systems (MEMS), where traditional oils wouldn’t fit. Oil evaporates and migrates, but a SAM based on tetradecanethiol stays quiet and does its job, helping tiny parts run clean and smooth.
Minding the Safety and Environmental Impact
Like a lot of organosulfur compounds, tetradecanethiol earns some unflattering marks for its smell and toxicity profile. Safety in handling, proper waste management, and good lab hygiene can’t get ignored. Years of working with it have taught me that even low concentrations escape into the air and stick to clothing—so fume hoods and gloves are standard. Greener alternatives deserve more research. Developing new, less toxic molecules with similar properties would not only reduce health risks but also ease environmental burdens. Until then, cautious handling and thoughtful experimental design stay vital.
| Names | |
| Preferred IUPAC name | tetradecane-1-thiol |
| Other names |
1-Tetradecanethiol
n-Tetradecyl mercaptan n-Tetradecanethiol Myristyl mercaptan |
| Pronunciation | /ˌtɛˌtrəˌdiːˈkeɪnˌθaɪˌɒl/ |
| Identifiers | |
| CAS Number | 143-13-5 |
| Beilstein Reference | 1209286 |
| ChEBI | CHEBI:35773 |
| ChEMBL | CHEMBL480314 |
| ChemSpider | 140367 |
| DrugBank | DB14109 |
| ECHA InfoCard | 100.218.649 |
| EC Number | 214-072-6 |
| Gmelin Reference | 66810 |
| KEGG | C06535 |
| MeSH | D000067612 |
| PubChem CID | 12072 |
| RTECS number | WN0897000 |
| UNII | 8K7T245WZ8 |
| UN number | UN3332 |
| CompTox Dashboard (EPA) | DTXSID8022516 |
| Properties | |
| Chemical formula | C14H30S |
| Molar mass | 246.48 g/mol |
| Appearance | Colorless liquid |
| Odor | Unpleasant. |
| Density | 0.845 g/mL at 25 °C |
| Solubility in water | Insoluble |
| log P | 6.29 |
| Vapor pressure | 0.000074 mmHg (25°C) |
| Acidity (pKa) | 10.6 |
| Basicity (pKb) | pKb = 3.62 |
| Magnetic susceptibility (χ) | -75.0e-6 cm³/mol |
| Refractive index (nD) | nD 1.444 |
| Viscosity | 3.2 mPa·s (20 °C) |
| Dipole moment | 1.60 D |
| Thermochemistry | |
| Std molar entropy (S⦵298) | 354.5 J·mol⁻¹·K⁻¹ |
| Std enthalpy of formation (ΔfH⦵298) | -276.3 kJ/mol |
| Std enthalpy of combustion (ΔcH⦵298) | -8890.7 kJ/mol |
| Pharmacology | |
| ATC code | V03AX |
| Hazards | |
| GHS labelling | GHS02, GHS07, GHS08 |
| Pictograms | GHS07, GHS08 |
| Signal word | Warning |
| Hazard statements | H226, H302, H311, H315, H318, H335, H400 |
| Precautionary statements | H226, H302, H315, H319, H335, P210, P261, P264, P270, P271, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362+P364, P403+P233, P405, P501 |
| Flash point | 113 °C |
| Autoignition temperature | 235 °C |
| Lethal dose or concentration | LD50 (oral, rat): 5100 mg/kg |
| LD50 (median dose) | LD50 (median dose): Oral rat > 2 g/kg |
| NIOSH | NA1993 |
| PEL (Permissible) | Not established |
| REL (Recommended) | 15 to 30°C |
| IDLH (Immediate danger) | Unknown |
| Related compounds | |
| Related compounds |
Dodecanethiol
Hexadecanethiol Octadecanethiol Tetradecanoic acid Tetradecanol |
