Dithiodiglycolic Acid: A Deep Dive Into Its Development and Applications
Historical Development
Dithiodiglycolic acid has been in chemists’ labs since the early years of organosulfur chemistry. You start to see its mention as researchers sought out better ways to link sulfur atoms within small molecules. Early synthesis paths relied heavily on laborious methods, yet the value people saw in the molecular structure—essentially a glycolic acid with two sulfur atoms pincered in the backbone—kept it under the eyes of academic and industrial labs. In the late 20th century, more straightforward synthetic approaches emerged, allowing for improved purity and scalability. These advances helped shift the molecule out of niche research circles and into the broader fabric of specialty chemical manufacturing. As scientists uncovered new reactions and modifications involving sulfur groups, dithiodiglycolic acid solidified its status as an interesting building block, especially as multidisciplinary research in pharmaceuticals, polymers, and electronics opened up new avenues for exploration.
Product Overview
At its core, dithiodiglycolic acid stands as a bridge between the world of simple small molecules and the vast landscape of functionalized sulfur compounds. Commercial forms usually arrive as a crystalline powder, ready for use in both experimental and industrial settings. With the combination of carboxylic acid and disulfide groups, it offers diverse reactivity that makes it appealing in the creation of advanced materials, chelating agents, and biochemical tools. Its accessibility in the market depends on demand from key applications, so suppliers often cater to specific purity grades based on customer needs—ranging from technical grade for large-scale processes to high-purity material for sensitive research.
Physical & Chemical Properties
Dithiodiglycolic acid has a formula of C4H6O4S2. With enough familiarity, you recognize its distinct odor and slightly yellowish appearance. The molecule dissolves well in water and many polar solvents, which makes it easy to deploy in numerous reaction environments. As the two carboxyl groups stand out as sites for hydrogen bonding, you get some unique solubility behavior compared to many other disulfides. Melting point sits around 120°C, but heating brings out decomposition before you reach boiling, typical for molecules packing both sulfur bonds and carboxyl ends. Chemists value its reactivity—especially the disulfide bridge, which responds to reduction and exchange reactions, offering a handy handle for attaching different chemical groups.
Technical Specifications & Labeling
Manufacturers list information specific to both safety and chemical quality: molecular weight at about 182 g/mol, CAS number 123-93-3, and purity specs often run as high as 99% for sensitive research. Safety labels feature classification as an irritant, recommendations for gloves and goggles, and suggestions for well-ventilated storage areas apart from oxidizing agents. Technical data sheets note storage temperatures of 2–8°C and make it clear that packaging should remain tightly closed to minimize moisture uptake. Anyone buying in bulk sees labels quoting batch numbers, expiry, and key analytics—titration results, residual solvents, and the expected content for heavy metals.
Preparation Method
A tried-and-tested preparation method involves oxidizing thioglycolic acid under controlled conditions. In practice, labs bubble oxygen or pass mild oxidizers such as hydrogen peroxide through an aqueous solution of thioglycolic acid, monitoring temperature to keep unwanted side reactions at bay. This approach generates dithiodiglycolic acid with decent yield and keeps the synthesis straightforward enough for scale-up. After the oxidation, filtration and recrystallization clean up the product. You can tailor some details if you need higher purity or less coloration—using alternative oxidants or adjusting pH during workup.
Chemical Reactions & Modifications
The disulfide bond at the heart of dithiodiglycolic acid springs to life in redox transformations, making it a useful player for experiments involving reduction or thiol-disulfide exchanges. Both carboxylic acid groups open the door to esterification, amidation, or salt formation, granting you access to a swath of derivatives. You can use gentle reducing agents to cleave the disulfide, yielding two equivalents of thioglycolic acid and opening up routes to more specialized compounds. In peptide chemistry or drug delivery research, these disulfide linkages enable reversible conjugation—ideal for applications where bond breaking under biological conditions is desired.
Synonyms & Product Names
Dithiodiglycolic acid goes by several chemical names: 2,2'-Dithiodiacetic acid, Di(thioacetic acid), 2,2'-Dithiodiglycolic acid, and even some trade names coded for specific markets. These synonyms circulate especially among suppliers serving pharmaceuticals or fine chemical manufacturers. People working in regulatory fields refer to it by its CAS number to cut past confusion.
Safety & Operational Standards
Handling dithiodiglycolic acid means you contend with two key issues: irritation and environmental impact. Both vapor and dust irritate skin, eyes, and respiratory tract, so routine use of personal protective equipment—gloves, goggles, and lab coats—remains non-negotiable. Facilities minimize dust with sealed systems, and waste gets funneled to designated chemical disposal centers. Workers keep an eye on spill kits just in case, and site safety plans include first-aid measures for accidental contact. Emerging research flags its potential as a mild aquatic pollutant, so industries tracking emissions keep logs and regularly audit waste outflow to comply with environmental laws.
Application Area
Dithiodiglycolic acid carves out space in chelation chemistry, polymer crosslinking, and the design of biologically active compounds. Laboratories use it as a soft oxidizing agent to introduce disulfide bridges in peptides and proteins. Electroplating industries exploit its binding to heavy metals during bath preparation. Polymer researchers find that the presence of both disulfide and acid groups lets them fine-tune polymer networks for flexibility or degradability—imperative traits in smart materials and biomedical devices. Some agricultural chemists look at its derivatives as tools to bind soil contaminants, though regulatory review for such uses takes time. Pharmaceutical research investigates modified forms for targeted drug delivery systems where a triggered release is needed inside the body.
Research & Development
Current R&D work covers tuning the synthesis for greener chemistry, hunting for new catalysts, and designing safer, more biodegradable derivatives. A growing push from environmental guidelines presses researchers to minimize hazardous intermediates, seeking milder oxidants or solvents with a lower carbon footprint. In pharma, teams dig into tailoring release kinetics of drug conjugates, leveraging the bond-splitting behavior of the disulfide linkage in physiological conditions. Material science draws on the molecule to create smart coatings responding to pH or redox state. Collaboration between academic labs and industry partners accelerates the shift from proof-of-concept to commercial application, with annual conferences showcasing progress and revealing gaps needing attention.
Toxicity Research
Toxicologists treat dithiodiglycolic acid with respect—studying its effects across bacteria, aquatic species, and mammals. Acute studies tend to show low-to-moderate oral toxicity in rodents, with irritation as the prime concern in repeated exposure. Long-term studies remain sparse, but risk assessors document no bioaccumulation in typical settings so far. Regulatory reports focus on its breakdown in soil and water, confirming that disulfide bridges grab the attention of environmental chemists who model persisting sulfur compounds. Workplace safety surveys monitor employee exposures, and recent years have seen calls for further testing around endocrine disruption and chronic toxicity.
Future Prospects
Looking ahead, as industries lean harder on green chemistry, demand grows for functional chemicals that balance utility with low legacy pollution. Dithiodiglycolic acid’s dual-reactive nature lends itself to novel applications in biomedicine and smart materials—areas where biodegradable linkages and dynamic molecular switches hold value. Startups and big labs alike eye its derivatives as next-generation crosslinkers for hydrogels and resins, especially in wound care and advanced manufacturing. Regulators and researchers both seek robust long-term safety data, nudging industry toward better lab practices and transparency. As my own work in R&D has shown, revisiting classic compounds through the lens of sustainability often brings a fresh wave of creativity—especially when the aim is to deliver practical safety, real performance, and novel problem-solving to the industries that shape daily life.
The Backbone of Select Chemical Processes
Dithiodiglycolic acid often shows up as a quiet workhorse in a lab or factory. It’s not a chemical you hear about over coffee conversations, but it definitely shapes some interesting corners of modern chemistry. As someone who has spent a fair bit of time around analytical labs, this compound stands out because of its unique sulfur-sulfur bond, which plays a key part in how it reacts with other substances.
Where Dithiodiglycolic Acid Pops Up
In specialty chemical research and the production of fine chemicals, chemists often turn to dithiodiglycolic acid as a building block for synthesizing complex molecules. Its structure lets it serve as a precursor for other organosulfur compounds. If you look into pharmaceuticals or custom synthesis, you’ll see that researchers like using compounds such as dithiodiglycolic acid to construct molecules that might block or encourage biological activity. For instance, tweaking a molecule’s structure with a dithiol group sometimes means the difference between a promising drug and an ineffective one.
Researchers also explore dithiodiglycolic acid as a chelating agent, meaning it can grab onto metals and hold them in solution. Removing heavy metals in industrial processes or even treating wastewater can hinge on having a chemical with this kind of ability. In my own work treating lab waste, I saw how organosulfur compounds could bind to troublesome impurities and help separate them from everything else. Environmental engineers already know how tough it is to pull toxic metals out of a system, and chemicals like dithiodiglycolic acid definitely help.
Plastics, Polymers, and Material Science
In polymer chemistry, dithiodiglycolic acid enters the mix as a chain transfer agent or as a crosslinking reagent. That means it helps to control the length of polymer chains, which can totally change a material’s toughness or flexibility. Consider things like coatings or specialty rubbers—tiny tweaks on the molecular level make a mountain of difference in how those materials hold up. Sometimes, adding the right dithiol structure means you get a product that resists cracking or can stretch without breaking. That’s pretty crucial, especially if the material ends up on a bridge or in a factory assembly line.
Challenges and Future Prospects
Dithiodiglycolic acid is not a household name, partly because safety and environmental rules drive how and where it gets used. The sulfur content means handling and disposal need care, especially in large batches. People concerned about groundwater and air quality should keep an eye on where and how these compounds move through production pipelines.
Every industry that uses powerful chemicals also deals with the responsibility of safe handling. Companies and researchers rely on solid protocols and robust training. Looking forward, chemists keep searching for ways to make these processes greener—reducing waste, recycling used chemicals, and designing molecules to break down safely at the end of their life cycles.
Knowledge Builds Trust
Anyone working in a field with organosulfur compounds should dig into the literature and safety data, not just take a supplier’s word for it. Knowing a little more about what’s inside the bottles on a laboratory shelf means fewer surprises and safer outcomes for everyone.
Structure and Form
Dithiodiglycolic acid stands out in the lab for its unique structure—two carboxylic acid groups bridged by a disulfide linkage. This setup gets any chemist’s attention. You’re looking at a molecule with the formula HOOC-CH2-S-S-CH2-COOH. Each end brings the acidic proton of a carboxyl group. In the middle, a sulfur-sulfur bond brings a set of chemical quirks you don’t see every day. The solid comes as a white crystal, grabs hold of water from the air, and doesn’t dissolve easily in most organic solvents. It mixes well in water, thanks to those two acid groups pulling in H2O molecules.
A Closer Look at Acidity and Redox
This acid doesn’t play around—each carboxyl brings a punch in terms of acidity. Aqueous solutions drop the pH fast. The double carboxylate function means it’s a diacid. Between those groups, you get a sulfur bridge that can get reduced to two thiols or oxidized under the right conditions. Disulfide bridges are fragile when asking around for electrons, so dithiodiglycolic acid works as a redox agent in certain settings. That bridge breaks apart quite easily, especially under reducing conditions.
How I’ve Used It
Back in grad school, I spent a semester in a lab focused on sulfur chemistry—honestly, you either love it, or you’re running away from the smell. Dithiodiglycolic acid made it into a few projects. We used it for disulfide exchange reactions. Adding just the right reducing agent split it into two molecules of thioglycolic acid. This property made it handy in making specialty polymers and tweaking protein folding. Sulfur bridges set many biological molecules apart, and this acid mirrored some of those structures. Getting hands-on experience grounded textbook chemistry.
Potential Hazards and Handling
Not everything labeled “acid” means “danger,” but caution doesn’t hurt. Dithiodiglycolic acid does more than sting when spilled; with repeated exposure, the sulfur components can irritate skin and lungs. Always respect chemicals carrying both carboxyl and sulfur groups. I watched a colleague learn the hard way after careless handling—the smell lingered for hours. Always glove up and work in a fume hood. Accidental spills on metal can corrode surfaces, and the acid may release unpleasant gases when heated. Storage calls for a cool, dry spot away from bases and oxidizing agents.
Why It Matters to Industry and Research
This acid catches attention beyond university labs. It’s found a place in specialty organic synthesis, especially for making disulfide-rich compounds. Resin chemists sometimes use it for cross-linking or manipulating surface reactions thanks to that reactive disulfide core. Pharmaceutical researchers keep an eye on these compounds for drug design, especially in targeting cysteine residues. In environmental labs, its presence can hint at the breakdown of pesticides or plastics containing thioethers.
Room for Improved Safety and Process Design
Tackling the challenges of sulfur-rich compounds means more than just following a safety checklist. Automatic air handling and spill monitoring in labs would prevent a lot of headaches. Industries could benefit from sealed reaction setups with continuous monitoring for sulfur gas release. Training programs for students should take them beyond textbook warnings—let them see the effects in a real setting, with proper precautions.
Final Thought
Every molecule carries a story. With dithiodiglycolic acid, the lessons stretch from hands-on synthesis to the way it shapes safety protocols and sparks new research avenues. Solid lab habits make the difference between a useful experiment and an unwelcome emergency. From my corner of the bench, respect for both substance and system lets chemistry push boundaries while keeping people and equipment safe.
Real Risks in Everyday Context
Dithiodiglycolic acid pops up in chemistry labs and specialty industries. Few folks outside those circles ever hear about it, but the stuff matters when talking about safety and toxicity. This compound features sulfur, which already hints at serious caution. Think about common household materials—bleach, solvents, motor oil. Most people understand to keep them out of reach and use gloves. Dithiodiglycolic acid deserves at least the same level of respect.
What’s Known From Research
I’ve spent time in a university lab, and I’ve seen first-hand how mishandling chemicals with strange names can quickly lead to trouble. Dithiodiglycolic acid is no exception. Safety documents warn about the risks: skin irritation, eye damage, and potential harm if inhaled. A typical example: a friend prepared a sulfur compound, and dropping some on his skin left a nasty burn. Dithiodiglycolic acid belongs to that family—contact means danger.
Breathing vapors, swallowing the substance, or splashing it in the eyes often brings much worse results than a short-term sting. In a world where workplace accidents keep climbing, this hazard profile should not stay hidden on some manufacturer’s safety sheet. Users deserve up-front clarity. According to safety assessments published by bodies like the European Chemicals Agency, exposure should stay extremely limited. The material can trigger strong irritation and possible toxic reactions in organs, based on studies in animals. No consumer product should include it in unregulated amounts.
Environmental and Long-Term Concerns
When spills happen or factories dump waste, chemicals rarely stay quiet. Sulfur atoms found in dithiodiglycolic acid break down unevenly, sometimes leaving behind products that pollute water or linger in soil. It doesn’t get diluted and disappear like a pinch of salt in soup. The Environmental Protection Agency highlights persistent chemicals as a problem for fish, wildlife, and sometimes drinking water supplies. Neighbors who rely on well water worry most. So do people who fish or swim near manufacturing hubs.
Why Standards and Training Matter
My old chemistry professors drilled one lesson into my head: “If you wouldn't pour it in your hand, don’t pour it down the drain.” Rules matter for more than just legal compliance. Anyone handling dithiodiglycolic acid needs strong training and the proper gear—goggles, gloves, lab coats, proper ventilation. Labels and data sheets need plain language, not buried technical detail. Without resources or regular reviews, employees could make mistakes that affect not just themselves but everyone nearby.
Better Solutions and Safer Practices
There's no benefit in brushing aside risks. Software that tracks chemical inventories helps flag dangerous stocks and checks that outdated materials get disposed responsibly. Regular inspections, access to medical checkups for anyone working directly with hazardous acids, and anonymous employee feedback all lower the chances of exposure and accident. And on the policy front, regulators should press for environmentally friendly alternatives and ongoing studies into long-term health impacts. After all, scientific understanding grows over time—standards should evolve, too.
Dithiodiglycolic acid brings serious hazards, whether used in industry or stored in a backroom shelf. Clear communication, strict handling, and up-to-date regulations keep everyone safer—and that’s a lesson worth repeating.
Why Extra Care Matters
Many chemicals deserve respect, but dithiodiglycolic acid puts that expectation up front. Anyone who’s worked in a lab knows the sharp scent, the corrosive splash, and the mess that follows a careless spill. This acid breaks down easily in water, latches on to metals, and eats through skin with alarming speed. That’s enough to remind anyone to check their habits and routines. Mistakes with strong acids leave marks, and dithiodiglycolic acid holds its own in the risk department.
Keeping It Locked Down: Storage Essentials
Storage matters as much as handling. A cool, dry spot works best, away from light and out of reach of moisture sources. Too many times, a busy workspace leads to bottles getting tucked under fume hoods or shoved behind other stock. That shortcut lets heat and humidity sneak in, which can change acid strength and set off reactions. I’ve seen leaking bottles damage shelving, and it doesn’t just ruin a day—it can pull down workplace safety compliance and trigger emergency calls.
Keep containers tightly sealed—no half-closed caps or “temporary” lids. Check bottle condition regularly. The acid attacks ordinary glass, so only bottles rated for corrosive chemicals earn a place on the shelf. Polyethylene and amber glass usually handle the job, but never guess. Old labels fade. Keep them legible so no one scrambles to look up contents after a decade in storage.
Getting the Details Right: Handling in Real Life
Handling isn’t just about gloves. That’s the easy, obvious part. Goggles, well-fitted lab coats, and face shields do more than tick boxes—they shield against splashes that show up faster than reflexes can react. Always work under a good fume hood. Any acid strong enough to irritate lungs at low concentrations deserves respect. Inhalation incidents happen fast, and the body notices right away.
Never trust a single set of gloves. I’ve been burned through pinholes that looked harmless on inspection. Nitrile often works for a short time, but have a backup layer if possible, especially if handling larger quantities or cleaning up unexpected spills. Practice with spill kits before an emergency happens. Real-world experience shows most teams freeze on first contact. Absorbent material, neutralizing agents, and safe waste bins cut down on panic and reduce the need for outside intervention.
Training, Trust, and Facts That Matter
Training keeps mistakes from turning into long-term problems. Workers assume they know what they’re doing until proven wrong by an accident. Relying too much on past experience skips over new safety research, improved PPE, and better storage guidelines. Regular walk-throughs and spot checks help spot leaks, loose caps, and labeling problems. Digital inventory systems aren’t just bureaucratic—they catch missing materials before anyone else notices.
According to the European Chemicals Agency, dithiodiglycolic acid can damage skin, eyes, and the respiratory system. Their guidance supports keeping acids away from bases, organic solvents, and, if possible, out of rooms with open drains or unprotected electrical systems. Mixing up storage locations or shelving incompatible chemicals side by side causes dangerous surprises, often when handling time is short.
Solutions Worth Considering
Store what you need, not what you hope to use. Regular waste disposal clears the decks for new projects and lowers the chance of old, decomposing acid building up. Use secondary containment trays under bottles for extra insurance. Most importantly, involve everyone, from management to bench staff, in the discussion. Safety works best when it isn’t just a rule but a shared value.
What You Need to Know
Dithiodiglycolic acid often pops up in research labs and specialty chemical projects. It isn’t something you grab at hardware stores or on everyday e-commerce sites. This compound gets plenty of attention for its applications in organic synthesis and as a building block in more advanced chemistry. Still, tracking down a supplier sometimes feels like hunting for a needle in a haystack, especially for folks not tied to an institution.
Finding Reliable Suppliers
While running a research group, I noticed how certain chemicals get a lot harder to buy once you leave a university environment. Dithiodiglycolic acid fits right into that category. The most straightforward route goes through established chemical supply companies. Sigma-Aldrich, Alfa Aesar, and TCI America supply it in small quantities mostly to institutional buyers. These businesses ask for a business license, and they vet buyers to follow safety and legal guidelines. Casual buyers and hobbyists usually won't get much traction with them — it's for safety and for compliance with chemical regulations.
Ordering through smaller specialty distributors sometimes works, especially in Europe or the US. Look into Fluorochem, Oakwood Chemical, or ChemSpace. They are geared toward specialists but may have different barriers to entry. Always check credentials, and don't accept blind offers through random online marketplaces. Counterfeit or mislabeled chemicals pose a real risk, both for safety and for research outcomes.
Safety Matters and Documentation
Chemicals like dithiodiglycolic acid require careful handling — suppliers enforce this by asking for end-use forms and safety certifications. Even in my own purchasing days, every unfamiliar compound needed approval from our environmental health and safety office. At home or in small outfits, the cost and paperwork can stop your project before it even starts. Suppliers rarely cut corners here, and that protects both you and everyone around.
What to Expect on Price
The price for dithiodiglycolic acid swings wildly depending on quantity and purity. Academic or high-purity grades (98% and up) usually start around $150 to $250 for 25 grams in the United States. Larger bulk purchases drop the per-gram price, but minimum order amounts can skyrocket the total. Shipping and hazardous materials fees also add to the bill; some suppliers demand orders above a certain amount before shipping anything, particularly for chemicals that require specialized containers.
If someone offers you a bottle for $20, slow down and ask questions. Reputable vendors post clear specifications with the product, and expect you to ask about batch certifications, shelf life, and storage. Purchasing from trusted companies limits hassle down the road—and sometimes saves your equipment from contamination. A few times, I pinched pennies buying from obscure sources, only to realize purity claims didn’t hold up under analysis, costing the project in wasted time.
Building Smarter Solutions
Research labs and industries can benefit from clearer, more transparent purchasing channels for specialty chemicals. Accessibility could improve with more resellers offering small-quantity, verified stock to vetted buyers. A shared, open database of legitimate chemical distributors also helps, fostering responsible, above-the-table trade. Proactive communication with suppliers about intended use and storage facilities will smooth the process, saving both sides from future headaches.
Public access to credible pricing information empowers independent researchers and small companies, keeping them from getting gouged or duped. That kind of transparency lets people spend less time navigating red tape and more time on their actual work, which always struck me as the most productive approach.
| Names | |
| Preferred IUPAC name | 2,2'-dithiodiacetic acid |
| Other names |
Dithioglycollic acid
Dithiodiacetic acid |
| Pronunciation | /daɪˌθaɪ.oʊˌdaɪˌɡlɪˈkɒl.ɪk ˈæs.ɪd/ |
| Identifiers | |
| CAS Number | 123-93-3 |
| Beilstein Reference | 678032 |
| ChEBI | CHEBI:28541 |
| ChEMBL | CHEMBL489872 |
| ChemSpider | 14032 |
| DrugBank | DB14011 |
| ECHA InfoCard | 100.012.055 |
| EC Number | 211-186-9 |
| Gmelin Reference | 67638 |
| KEGG | C02936 |
| MeSH | D05.700.400.400.400 |
| PubChem CID | 8778 |
| RTECS number | KL2975000 |
| UNII | 5B8U5B8K34 |
| UN number | UN2811 |
| CompTox Dashboard (EPA) | DTXSID9044372 |
| Properties | |
| Chemical formula | C4H6O4S2 |
| Molar mass | 154.19 g/mol |
| Appearance | White crystalline powder |
| Odor | Odorless |
| Density | 1.56 g/cm³ |
| Solubility in water | Soluble |
| log P | -1.2 |
| Vapor pressure | 0.02 mmHg (25°C) |
| Acidity (pKa) | 2.78 |
| Basicity (pKb) | 1.76 |
| Magnetic susceptibility (χ) | -49.7·10⁻⁶ cm³/mol |
| Refractive index (nD) | 1.701 |
| Viscosity | Viscous liquid |
| Dipole moment | 2.21 D |
| Thermochemistry | |
| Std molar entropy (S⦵298) | 210.5 J·mol⁻¹·K⁻¹ |
| Std enthalpy of formation (ΔfH⦵298) | -631.9 kJ/mol |
| Std enthalpy of combustion (ΔcH⦵298) | -840.7 kJ/mol |
| Hazards | |
| Main hazards | Harmful if swallowed, causes skin and serious eye irritation |
| GHS labelling | GHS05, GHS07 |
| Pictograms | GHS05 |
| Signal word | Danger |
| Hazard statements | H302: Harmful if swallowed. |
| Precautionary statements | P261, P264, P270, P271, P301+P312, P304+P340, P312, P330, P403+P233, P405, P501 |
| NFPA 704 (fire diamond) | 2-1-2 |
| Flash point | 113 °C |
| Autoignition temperature | 215 °C |
| Explosive limits | No explosive limits found. |
| Lethal dose or concentration | LD50 oral rat 570 mg/kg |
| LD50 (median dose) | LD50 (median dose): Rat oral 220 mg/kg |
| NIOSH | Not Listed |
| PEL (Permissible) | Not established |
| REL (Recommended) | 25 g/L |
| Related compounds | |
| Related compounds |
Thioglycolic acid
Mercaptoacetic acid Dithioglycolic acid Oxalic acid |
