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Propargyl Alcohol (propynol) is a clear colourless to pale yellow oil.
Propargyl Alcohol (propynol), known as 2-propyn-1-ol, is a colourless flammable liquid with a pleasant odour.
Propargyl Alcohol (propynol) has a wide range of applications and plays an important role in scientific research and industrial processes.
CAS Number: 3973-18-0
Molecular Formula: C5H8O2
Molecular Weight: 100.12
EINECS Number: 223-601-1
Synonyms: PROPARGYL ALCOHOL, Prop-2-yn-1-ol, 2-Propyn-1-ol, 107-19-7, Ethynyl carbinol, 2-Propynyl alcohol, Ethynylcarbinol, 1-Propyn-3-ol, Methanol, ethynyl-, Propynyl alcohol, 2-Propynol, 3-Propynol, 1-Hydroxy-2-propyne, 3-Hydroxy-1-propyne, Acetylenylcarbinol, Acetylene carbinol, Propiolic alcohol, Agrisynth PA, RCRA waste number P102, NSC 8804, prop-2-yne-1-ol, Prop-2-in-1-ol, CCRIS 6781, propargylalcohol, 1-Propyn-3-yl alcohol, HSDB 6054, EINECS 203-471-2, UNII-E920VF499L, BRN 0506003, DTXSID5021883, CHEBI:28905, AI3-24359, E920VF499L, NSC-8804, HC.$.CCH2OH, PROPARGYL ALCOHOL [MI], DTXCID301883, PROPARGYL ALCOHOL [HSDB], EC 203-471-2, 4-01-00-02214 (Beilstein Handbook Reference), Propargyl alcohol [NA1986] [Flammable liquid], 2-propyne-1-ol, MFCD00002912, NA1986, RCRA waste no. P102, ethynylmethanol, 1Propyn3ol, 2Propyn1ol, 2Propynyl alcohol, prop-2-ynol, propyn-3-ol, 1-Propyne-3-ol, 2-propyn-1 ol, prop-2-yn-I-ol, prop-1-yn-3-ol, ETHYNOL CARBINOL, ETHYNYL METHANOL, Propargyl alcohol, 99%, CARBINOL, ETHYNYL-, bmse000363, HYDROXYMETHYLACETYLENE, WLN: Q2UU1, CHEMBL1563026, NSC8804, Propargyl alcohol (ACGIH), Tox21_200976, BBL011350, STL146440, AKOS000118737, NA 1986, NCGC00091559-01, NCGC00091559-02, NCGC00258529-01, BP-30161, CAS-107-19-7, NS00003754, P0536, EN300-19326, C05986, Q903345.Propynol ethoxylate,PEPSTATIN A METHYL ESTER,PME,Ethylene glycol monopropargyl ether,ISOVALERYL-V-V-STA-A-STA-OCH3,ISOVALERYL-W-STA-A-STA-OCH3,3-(2-Hydroxyethoxy)-1-propyne,2-(prop-2-ynyloxy)ethanol, Propargyl-PEG2-alcohol has propargyl and alcohol end groups. The propargyl can participate in copper-catalyzed Click Chemistry reactions with azides.
Propargyl Alcohol (propynol) is used as a fuel, solvent and reagent in chemical reactions, as well as an important ingredient in the manufacture of many pharmaceuticals and industrial products.
In scientific research, Propargyl Alcohol (propynol) is used as a reagent in organic synthesis, as a solvent in analytical chemistry and as a fuel in combustion studies.
This volatile organic compound (VOC) occurs naturally in plants and animals and can also be synthesised in a laboratory environment.
Propargyl Alcohol (propynol), or 2-propyn-1-ol, is an organic compound with the formula C3H4O.
Propargyl Alcohol (propynol) is the simplest stable alcohol containing an alkyne functional group.
Propargyl Alcohol (propynol) is a colorless viscous liquid that is miscible with water and most polar organic solvents.
Propargyl Alcohol (propynol), also known as propynol (C₃H₄O), is an organic compound with the molecular formula HC≡CCH₂OH.
It is a colorless, flammable liquid with a slightly sweet odor.
The structure of propargyl alcohol consists of a hydroxyl group (-OH) attached to a propynyl group (an alkyne, -C≡C-), making it an alcohol and an alkyne.
Propargyl Alcohol (propynol) is commonly used as a building block in organic synthesis for producing other chemicals, such as pharmaceuticals, agrochemicals, and fragrances.
Propargyl Alcohol (propynol) is used in some industrial applications, particularly in oil and gas industries, as a corrosion inhibitor to protect metals from acid corrosion.
In polymerization reactions, Propargyl Alcohol (propynol) can be used to introduce functional groups or create cross-linked structures in polymers.
Propargyl Alcohol (propynol) can be used as an additive in fuel compositions for its reactive alkyne group.
Propargyl Alcohol (propynol), or 2-propyn-1-ol, is an organic compound with the formula C3H4O.
It is the simplest stable alcohol containing an alkyne functional group.
Propargyl Alcohol (propynol) is a colorless viscous liquid that is miscible with water and most polar organic solvents
Propargyl Alcohol (propynol) is a primary alcohol that contains an alkyne group, meaning it has both a hydroxyl group (-OH) and a triple bond between two carbon atoms (-C≡C-).
The alkyne structure makes propargyl alcohol more reactive than many other alcohols.
Propargyl Alcohol (propynol) polymerizes with heating or treatment with base.
It is used as a corrosion inhibitor, a metal complex solution, a solvent stabilizer and an electroplating brightener additive.
Propargyl Alcohol (propynol) is also used as an intermediate in organic synthesis.
Secondary and tertiary substituted propargylic alcohols undergo catalyzed rearrangement reactions to form α,β-unsaturated carbonyl compounds via the Meyer–Schuster rearrangement and others.
Propargyl Alcohol (propynol) can be oxidized to propynal or propargylic acid.
As an indication of the electronegativity of an sp carbon, propargyl alcohol is significantly more acidic (pKa = 13.6) compared to its sp2-containing analog allyl alcohol (pKa = 15.5), which is in turn more acidic than the fully saturated (sp3 carbons only) n-propyl alcohol (pKa = 16.1).
Propargyl Alcohol (propynol) is produced by the copper-catalysed addition of formaldehyde to acetylene as a by-product of the industrial synthesis of but-2-yne-1,4-diol.
It can also be prepared by dehydrochlorination of 3-chloro-2-propen-1-ol by NaOH.
Propargyl Alcohol (propynol) is a clear colorless liquid with a geranium-like odor.
Propargyl Alcohol (propynol) is used to make other chemicals, as a corrosion inhibitor and a soil fumigant.
Propargyl Alcohol (propynol), or 2-propyn-1-ol, is an organic compound with the formula C3H4O of Propargyl Alcohol (propynol) is the simplest stable alcohol containing an alkyne functional group.
Propargyl Alcohol (propynol) is a colorless viscous liquid that is miscible with water and most polar organic solvents.
Reactions and applications of Propargyl Alcohol (propynol) polymerizes with heating or treatment with base.
Propargyl Alcohol (propynol) is used as a corrosion inhibitor, a metal complex solution, a solvent stabilizer and an electroplating brightener additive.
Propargyl Alcohol (propynol) is also used as an intermediate in organic synthesis.
Secondary and tertiary substituted propargylic alcohols undergo catalyzed rearrangement reactions to form α,β-unsaturated carbonyl compounds via the Meyer-Schuster rearrangement and others.
Propargyl Alcohol (propynol) can be oxidized to propynal or propargylic acid.
Propargyl Alcohol (propynol) is a solvent stabilizer that is useful as an intermediate in organic synthesis, an electroplating brightener additive.
Propargyl Alcohol (propynol) is useful 3-carbon fragment in acetylene coupling reactions, Propargyl Alcohol (propynol) undergoes Pd-catalyzed O-coupling with alcohols to give the corresponding 1-methoxyallyl ethers.
When phosphorus pentaoxide is added to Propargyl Alcohol (propynol), caused ignition.
Acetyl bromide reacts violently with alcohols or water.
Mixtures of alcohols with concentrated sulfuric acid and strong hydrogen peroxide can cause explosions.
Example: An explosion will occur if dimethylbenzylcarbinol is added to 90% hydrogen peroxide then acidified with concentrated sulfuric acid.
Mixtures of ethyl alcohol with concentrated hydrogen peroxide form powerful explosives.
Mixtures of hydrogen peroxide and Propargyl Alcohol (propynol) tend to explode if acidified with 70% sulfuric acid.
Propargyl Alcohol (propynol)s are violently explosive.
They are readily obtained by reacting hypochlorous acid and alcohols either in aqueous solution or mixed aqueous-carbon tetrachloride solutions.
Chlorine plus alcohols would similarly yield alkyl hypochlorites
Propargyl Alcohol (propynol) can be oxidized to produce propargyl aldehyde (propynal) or further to propiolic acid (HC≡C-COOH).
Due to the triple bond, propargyl alcohol can undergo nucleophilic addition reactions with halogens, hydrogen halides, or undergo catalytic hydrogenation to produce allyl alcohol.
Propargyl Alcohol (propynol) can be esterified in the presence of acetic acid to form propargyl acetate, which has applications as a chemical intermediate.
The triple bond can be used in cross-linking reactions for the production of specialized polymers.
The triple bond in propargyl alcohol makes it a versatile intermediate for synthesizing complex organic molecules, including drug compounds.
Some pharmaceuticals containing propargyl groups have been developed for their ability to act as enzyme inhibitors, such as MAO-B inhibitors used in Parkinson’s disease.
Propargyl Alcohol (propynol) is used in the synthesis of pesticides and herbicides, leveraging its ability to modify chemical structures effectively.
In the oil and gas industry, Propargyl Alcohol (propynol) is added to corrosion inhibitors to protect pipelines and other equipment exposed to acidic environments, such as hydrochloric acid.
Its derivatives are used in the manufacturing of coatings and lubricants for semiconductors and other electronic components.
Boiling point: 80-90 °C(Press: 12-14 Torr)
Density: 1.0261
refractive index: 1.4502
storage temp.: Sealed in dry,Store in freezer, under -20°C
solubility: Chloroform (Sparingly), Ethyl Acetate (Slightly)
form: Oil
pka: 14.22±0.10(Predicted)
color: Colourless to Pale Yellow
Stability: Light Sensitive
InChI: InChI=1S/C5H8O2/c1-2-4-7-5-3-6/h1,6H,3-5H2
InChIKey: GHGCQQRMJCSIBQ-UHFFFAOYSA-N
SMILES: C(O)COCC#C
Propargyl Alcohol (propynol) polymerizes with heating or treatment with base.
Propargyl Alcohol (propynol) is used as a corrosion inhibitor, a metal complex solution, a solvent stabilizer and an electroplating brightener additive.
Propargyl Alcohol (propynol) is also used as an intermediate in organic synthesis.
Secondary and tertiary substituted propargylic alcohols undergo catalyzed rearrangement reactions to form α,β-unsaturated carbonyl compounds via the Meyer-Schuster rearrangement and others.
Propargyl Alcohol (propynol) can be oxidized to propynal or propargylic acid.
Preparation of Propargyl Alcohol (propynol) is produced by the copper-catalysed addition of formaldehyde to acetylene as a by-product of the industrial synthesis of but-2-yne-1,4-diol.
Propargyl Alcohol (propynol) can also be prepared by dehydrochlorination of 3-chloro-2-propen-1-ol by NaOH.
Safety
Propargyl Alcohol (propynol) is a flammable liquid, toxic by inhalation, highly toxic by ingestion, toxic by skin absorption, and
corrosive.
Propargyl Alcohol (propynol) is quickly distributed and excreted following an iv dose.
The majority of the radioactivity ((14)Clabeled test material) was excreted in the urine and as carbon dioxide in the breath of both rats and mice.
Oral dosing resulted in a similar rapid (but slower than after iv dosing) excretion pattern, with the bulk of radioactivity being excreted in the urine and exhaled carbon dioxide.
Dermal absorption was low due to the volatility of Propargyl Alcohol (propynol).
Inhalation exposure resulted in 55 to 63% absorption of inhaled propargyl alcohol at 1 or 10 ppm and only 23 to 33% absorption at 100 ppm.
Both species eliminated the majority of the inhaled dose in urine.
While oxidative metabolism of low molecular weight primary alcohols is generally catalyzed by alcohol dehydrogenase, Propargyl Alcohol (propynol) is a relatively poor substrate for this enzyme.
Bovine liver catalase was used, to measure the rate of oxidative bioactivation of propargyl alcohol to 2-propyn-l-al.
Propargyl Alcohol (propynol) was/ found the rate to be higher than predicted and hypothesized that the oxidative biotransformation of propargyl alcohol to the more reactive alpha, beta-unsaturated aldehyde by liver catalase might be the initial step in propargyl alcohol induced liver injury.
Propargyl Alcohol (propynol) is stored in stainless steellined, glass-lined, or phenolic-lined tanks ordrums.
Unlined steel containers may be usedif free of rust.
Aluminum, rubber, and epoxymaterials should not be used.
Propargyl Alcohol (propynol) use protectivewear when handling.
The commercial material contains a stabiliser.
An aqueous solution of Propargyl Alcohol (propynol) can be concentrated by azeotropic distillation with butanol or butyl acetate.
Dry it with K2CO3 and distil it under reduced pressure, in the presence of about 1% succinic acid, through a glass helices-packed column.
Alcohols have a long history of myriad uses.
For simple mono-alcohols, which is the focus on this article, the following are most important industrial alcohols: methanol, mainly for the production of formaldehyde and as a fuel additive ethanol, mainly for alcoholic beverages, fuel additive, solvent
The chemical formula of Propargyl Alcohol (propynol) shown above is based on the molecular formula indicating the numbers of each type of atom in a molecule without structural information, which is different from the empirical formula which provides the numerical proportions of atoms of each type.
Personal protective equipment (PPE) like gloves, goggles, and respiratory masks should be worn when handling propargyl alcohol.
Propargyl Alcohol (propynol) should be stored in a cool, dry, well-ventilated area, away from sources of ignition and incompatible substances like oxidizing agents.
Uses Of Propargyl Alcohol (propynol):
Propargyl Alcohol (propynol) is an intermediate and it is shown to be used in the design and synthesis of a tag-free chemical probe for photoafiinity labeling.
Propargyl Alcohol (propynol) is a PEG-based PROTAC linker that can be used in the synthesis of PROTACs.
Propargyl Alcohol (propynol) is a click chemistry reagent, it contains an Alkyne group and can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) with molecules containing Azide groups.
Propargyl Alcohol (propynol) has been used as a key starting material in the [4+2] cycloisomerization mediated synthesis of various phthalide derivatives
Propargyl Alcohol (propynol) is used as a corrosion inhibitor, soil fumigant; solvent, stabilizer, and chemical intermediate.
Propargyl Alcohol (propynol) is stored in stainless steellined, glass-lined, or phenolic-lined tanks ordrums.
Ingestion In rats given oral Propargyl Alcohol (propynol) doses of 0, 5, 15 or 50 mg/kg body weight daily for 90 days, doses of 15 mg/kg body weight or more caused changes in haematological parameters (in the form of anaemia), increased relative liver weights, and histopathological changes in the liver (megalocytosis) and kidneys (karyomegaly in the tubule epithelia); at 50 mg/kg body weight, in addition increased relative kidney weights (male animals) and changes in clinico-chemical parameters were observed.
In this study the LOAEL (lowest observed adverse effect level) was 5 mg/kg body weight.
Similar effects were found after rats were given oral doses of the substance for 28 days.
Dermal absorption Epicutaneous application of Propargyl Alcohol (propynol) to the intact or scarified skin of rabbits for 91 days did not produce treatment-related effects up to the highest tested dose of 20 mg/kg body weight and day.
Local effects on skin and mucous membranes Undiluted Propargyl Alcohol (propynol) instilled into the conjunctival sac of the rabbit eye caused pain and erythema, oedema and clouding of the cornea.
The effects were still marked 8 days after the application. A 10 % aqueous solution produced mild pain reactions and only transient irritation.
Undiluted Propargyl Alcohol (propynol) applied to rabbit skin (dorsal) caused oedema, hyperaemia and necrosis.
Propargyl Alcohol (propynol), marked necrosis and anaemia were evident.
10 % solution caused slight hyperaemia and oedema, a 1 % solution did not have any effects.
Propargyl Alcohol (propynol) is used in metal plating and pickling and asa corrosion inhibitor of mild steel in mineral acids.
Propargyl Alcohol (propynol) also finds application in preventingthe hydrogen embrittling of mild steel inacids.
It is used as an intermediate for makingmiticide and sulfadiazine..
Propargyl Alcohol (propynol) is used to synthesize drugs, including certain enzyme inhibitors (e.g., monoamine oxidase-B inhibitors used in Parkinson's disease treatment).
Propargyl Alcohol (propynol) is used in the production of pesticides, herbicides, and plant growth regulators.
Certain derivatives of propargyl alcohol are employed in the manufacture of fragrance ingredients.
In the oil and gas industry, Propargyl Alcohol (propynol) is used as a corrosion inhibitor.
Propargyl Alcohol (propynol) helps protect metal surfaces, particularly in acidic environments, such as in pipelines or equipment that handle corrosive liquids like hydrochloric acid.
Propargyl Alcohol (propynol) forms a protective layer that reduces corrosion rates, extending the life of industrial equipment.
Propargyl Alcohol (propynol) is used in polymerization reactions, where it can help create cross-linked or specialized polymer structures.
Its triple bond allows it to participate in various polymer-forming processes.
Applied in protective coatings, including those for electronic components.
Propargyl Alcohol (propynol) is used in the production of specialized adhesives.
Propargyl Alcohol (propynol)-derived resins are used in manufacturing durable materials.
Propargyl Alcohol (propynol) can be used in fuel compositions as an additive to enhance performance.
Its high reactivity and alkyne structure can help improve combustion efficiency or modify fuel properties.
Due to its reactive hydroxyl and alkyne groups, Propargyl Alcohol (propynol) is utilized in the synthesis of specialty chemicals, such as:
Propargyl Alcohol (propynol) useful in industrial applications as solvents or intermediates.
Widely used in organic synthesis for further chemical transformations.
Propargyl Alcohol (propynol) is used to produce chemicals employed in coatings, lubricants, and other specialized applications within the semiconductor and electronics industries.
Its ability to introduce reactive alkyne groups helps modify surfaces or create protective layers in electronic devices.
Propargyl Alcohol (propynol) can be polymerized to form polyacetylene, a conductive polymer used in various electronic applications, such as batteries, sensors, and conducting films.
Propargyl Alcohol (propynol) is used in the surface treatment of metals and other materials to improve their adhesion properties or make them more chemically reactive for further processing, such as painting or coating.
In certain formulations, Propargyl Alcohol (propynol) can be used as a cross-linking agent in resins or adhesives.
The reactive triple bond can create strong covalent bonds between polymer chains, resulting in enhanced material strength and durability.
In academic and industrial research, Propargyl Alcohol (propynol) is frequently employed as a reagent or a precursor in various chemical reactions.
Its alkyne group allows for click chemistry, a popular technique used to rapidly synthesize new compounds.
Propargyl Alcohol (propynol) is used in the development of advanced materials like thermosetting resins, which are strong, heat-resistant polymers.
These materials are utilized in aerospace, automotive, and electronic applications due to their durability and high thermal stability.
In composite materials manufacturing, propargyl alcohol-based resins are used to bind fiber-reinforced composites (e.g., carbon fiber or glass fiber) in lightweight, high-strength applications.
Propargyl Alcohol (propynol) is an important reagent in click chemistry, a set of biocompatible reactions that allow rapid and specific joining of molecules.
This is particularly useful in drug discovery, bioconjugation, and diagnostics. In these reactions, the alkyne group in propargyl alcohol readily reacts with azides in a copper-catalyzed process to form stable triazoles, making it highly valuable for synthesizing biological probes and therapeutic agents.
Researchers use propargyl alcohol in click reactions to create complex bioactive molecules, helping to improve drug efficacy, stability, or delivery.
Propargyl Alcohol (propynol) derivatives, such as selegiline and rasagiline, are used as monoamine oxidase B (MAO-B) inhibitors in the treatment of neurodegenerative diseases like Parkinson's disease.
These compounds prevent the breakdown of dopamine in the brain, improving the motor symptoms associated with the disease.
The reactivity of propargyl alcohol has led to its use in the synthesis of new anticancer and antiviral drugs, where it serves as a key intermediate for introducing functional groups needed for activity.
Propargyl Alcohol (propynol) is used in the formulation of water treatment chemicals, where it acts as a corrosion inhibitor, particularly for protecting water-carrying pipelines and systems from acidic or oxidative damage.
This makes it valuable in industries such as power generation, where large amounts of water are circulated through equipment that can corrode over time.
In the mining and metallurgy industry, Propargyl Alcohol (propynol) is used as a reagent to assist in mineral extraction and processing.
Propargyl Alcohol (propynol) can be used in flotation processes, where it helps to separate valuable minerals from the surrounding ore by modifying the surface properties of the materials.
In the energy sector, Propargyl Alcohol (propynol) is a key component in formulations designed to inhibit corrosion in drilling fluids, refineries, and pipelines.
It is particularly useful in protecting against sulfidation or acidic corrosion, extending the life of drilling rigs and production equipment.
In hydraulic fracturing ("fracking") operations, Propargyl Alcohol (propynol) is sometimes added to fluids to protect equipment from chemical damage caused by harsh subterranean environments.
Propargyl Alcohol (propynol) is used as a starting material for the halogenation (addition of halogens like chlorine, bromine, etc.) and subsequent functionalization in the synthesis of fine chemicals.
These chemicals are then used in agrochemical, pharmaceutical, and specialty chemical industries.
It can act as an alkylating agent to introduce propargyl groups into molecules, giving rise to a variety of derivatives used in different industries.
Propargyl Alcohol (propynol) is involved in the production of specialty coatings and sealants.
The reactive alkyne functionality allows these coatings to cure quickly, creating durable protective layers on metals, plastics, and other surfaces.
These coatings are often employed in harsh environments, such as marine and offshore installations, where corrosion resistance is critical.
Propargyl Alcohol (propynol) can be used in CVD processes, where it acts as a precursor to deposit thin films of materials on substrates.
This is valuable in semiconductor manufacturing, where precision layering of materials is essential for producing microchips, sensors, and other electronic components.
In catalytic hydrogenation, the triple bond of Propargyl Alcohol (propynol) can be reduced to form allyl alcohol, which has further utility in the production of plastics, resins, and other chemicals.
The reaction is highly selective and widely used in organic synthesis.
Propargyl Alcohol (propynol) is used as a versatile reagent in academic and industrial laboratories.
Its ability to participate in both alkyne and alcohol reactions makes it a valuable tool for organic chemists who are synthesizing complex molecules.
In the adhesive industry, Propargyl Alcohol (propynol) is used to develop specialty adhesives with specific curing properties.
These adhesives are often employed in demanding applications such as aerospace and automotive manufacturing, where high-temperature resistance and strong bonding properties are required.
Propargyl Alcohol (propynol) is used to modify surfaces of materials at the nanoscale.
This helps to alter their chemical reactivity or introduce specific functionalities, such as hydrophobicity or enhanced adhesion.
Propargyl Alcohol (propynol) can be used in the production of nanocomposites where nanoparticles are embedded in polymers, leading to materials with enhanced mechanical, thermal, or electrical properties.
Safety Profile Of Propargyl Alcohol (propynol):
Propargyl Alcohol (propynol) is a flammable liquid, toxic by inhalation, highly toxic by ingestion, toxic by skin absorption, and corrosive.
Central nervous system depressant.
Propargyl Alcohol (propynol) may be fatal is absorbed through skin or inhaled.
Propargyl Alcohol (propynol) causes severe irritation.
High concentrations are extremely destructive to mucous membranes, upper respiratory tract, eyes and skin.
Symptoms of exposure may include burning sensation, coughing, wheezing, laryngitis, shortness of breath, headache, nausea, and vomiting.
Propargyl Alcohol (propynol) is toxic and highly flammable.
Propargyl Alcohol (propynol) can cause severe irritation to the skin, eyes, and respiratory system upon exposure, and ingestion or inhalation may lead to more serious health effects.
Propargyl Alcohol (propynol) is also classified as a hazardous substance and should be handled with proper safety precautions.
