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Propargyl alcohol

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Propargyl alcohol is a colorless, flammable liquid chemical compound. It is a primary alcohol with an alkyne functional group. Propargyl alcohol has the chemical formula C3H4O and is used as an industrial chemical in various applications.

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Lab products found in correlation

Sodium azide, by Merck Group (5 mentions) Copper 1 bromide, by Merck Group (4 mentions) Propargylamine, by Merck Group (3 mentions) Phenylacetylene, by Merck Group (3 mentions) Dimethyl sulfoxide (dmso), by Merck Group (3 mentions) Propargyl bromide, by Merck Group (2 mentions) Ethanol, by Merck Group (2 mentions) Tetrahydrofuran, by Merck Group (2 mentions) 4 dimethylaminopyridine, by Merck Group (2 mentions) Sodium l ascorbate, by Merck Group (2 mentions) N n dimethylformamide (dmf), by Merck Group (2 mentions) N n dicyclohexylcarbodiimide, by Merck Group (2 mentions) Sodium hydroxide (naoh), by Merck Group (2 mentions) Ethylenediamine, by Merck Group (2 mentions) Pmdeta, by Merck Group (2 mentions) Dimethylformamide, by Thermo Fisher Scientific (1 mentions) Ammonium chloride, by Thermo Fisher Scientific (1 mentions) Dimethyl sulfoxide (dmso), by Thermo Fisher Scientific (1 mentions) Methanol, by Thermo Fisher Scientific (1 mentions) 6 chloro 1 hexanol, by Merck Group (1 mentions)

23 protocols using propargyl alcohol

1

Synthesis of Photoactive Dental Monomers

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1,3-Bis(2-isocyanatopropan-2-yl)benzene, dibutyltin dilaurate, tetrahydrofuran, 6-chloro-1-hexanol, sodium azide, 1,1,1-tris(hydroxymethyl)propane, propargyl bromide, propargyl alcohol, bisphenol A diglycidyl ether, ethanol, 3-(triethoxysilyl)propyl isocyanate, copper(II) chloride, N,N,N′,N′,N″-pentamethyldiethylenetriamine (PMDETA), camphorquinone (CQ), ethyl 4-(dimethylamino)benzoate (EDAB), and acetonitrile were used as received from Sigma Aldrich. Sodium hydroxide, ammonium chloride, dimethyl sulfoxide, dimethylformamide, methanol, and sodium sulfate were used as received from Fisher Scientific. BisGMA/TEGDMA (70/30) comonomers solution was used as received from ESSTECH. Fusion silane coupling agent was used as received from George Taub Products & Fusion Co., Inc. Bis(6-azidohexyl) (1,3-phenylenebis(propane-2,2-diyl))dicarbamate (BZ-AZ) and 1-(prop-2-yn-1-yloxy)-2,2-bis((prop-2-yn-1-yloxy)methyl)butane (AK) were synthesized according to a previously reported procedure [60 (link)]. All azides were synthesized according to the azide safety rules and handled with appropriate precaution when working with monomers, resins, and polymers in small quantities [62 ].
Song H.B., Sowan N., Shah P.K., Baranek A., Flores A., Stansbury J.W, & Bowman C.N. (2016). Reduced shrinkage stress via photo-initiated copper(I)-catalyzed cycloaddition polymerizations of azide-alkyne resins. Dental materials : official publication of the Academy of Dental Materials, 32(11), 1332-1342.
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2

Synthesis of Vanillyl Alcohol Derivatives

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Propargyl bromide, propargyl alcohol, vanillyl alcohol, ferulic acid, clove oil, sodium azide, N,N′-dicyclohexylcarbodiimide solution (DCC) and 4-(dimethylamino)pyridine (DMAP) and were purchased from Sigma-Aldrich St. Louis, USA. Vanillin (100% purity) was purchased from Eternal Pearl (The Zhonghua Chemical Factory, Zhejiang, China). Coniferaldehyde and vanillic acid were previously isolated from Cocos nucifera L., as reported.26 Eugenol was extracted and purified from clove oil using 30% aqueous KOH, according to the literature.27
Elsbaey M., Igarashi Y., Ibrahim M.A, & Elattar E. (2023). Click-designed vanilloid-triazole conjugates as dual inhibitors of AChE and Aβ aggregation. RSC Advances, 13(5), 2871-2883.
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3

Preparation and Characterization of PullN3-PHBHV

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Figure 1 presents the chemical structure of PullN3 used in this work, with a degree of substitution of DS = 0.08, previously prepared and characterized as described in our last publication [29 (link)]. Poly(3-hydroxybutyrate-co-3-hydroxyvalerate) (PHBHV, 8.6% mol HV, produced by controlled fermentation process using microorganisms) with an average numerical molar mass (Mn) of 159,710 Da and dispersion (Ð) equal to 2.86, was purchased by Sigma-Aldrich (St. Louis, MO, USA). Tin dibutyl dilaurate (DBTB, 95%, Sigma-Aldrich, São Paulo, Brazil), copper bromide (CuBr, 98%, Sigma-Aldrich), N, N, N′, N’‘, N’’-pentamethyldiethylentriamine (PMDTA, 99%, Sigma-Aldrich), propargyl alcohol (99%, Sigma -Aldrich), deuterated dimethyl sulfoxide (DMSO-d6, 99.9%, Sigma-Aldrich) and deuterated chloroform (CDCl3, 99.8%, Sigma-Aldrich) were used as received. Toluene (P.A., Labsynth, São Paulo Brazil) was distilled at atmospheric pressure in the presence of calcium hydride (CaH2). N, N-dimethylformamide (DMF, 99.8%, Labsynth) was distilled under reduced pressure in the presence of calcium hydride (CaH2), and the water used in the entire process was distilled and deionized. Other solvents used in the polymer purification steps, such as, ethyl alcohol (P.A., Labsynth), methyl alcohol (P.A., Labsynth) and ethyl ether (P.A., Labsynth), were used without any prior purification.
T. de Carvalho L., da S. Paula M.L., M. de Moraes R., Alves G.M., M. Lacerda T., dos Santos J.C., M. dos Santos A, & Medeiros S.D. (2020). Chemical Modification of Pullulan Exopolysaccharide by Grafting Poly(3-hydroxybutyrate-co-3-hydroxyvalerate) (PHBHV) via Click Chemistry. Polymers, 12(11), 2527.
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4

Synthesis of Phthalocyanine Derivatives

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Propargyl alcohol, dichlorosilicon (IV) phthalocyanine, copper(II) sulphate pentahydrate, sodium-L-ascorbate, NaN3, iodine monochloride and all solvents were purchased from Sigma Aldrich (Saint Louis, MO, USA). All reactions were carried out under a dry argon atmosphere unless otherwise noted. Column chromatography for the purification of the crude compounds was performed on silica gel 60. The purity of the products was tested at each step using thin layer chromatography (silica gel F-254 coated TLC plates).
Polyakov M., Ivanova V., Klyamer D., Köksoy B., Şenocak A., Demirbaş E., Durmuş M, & Basova T. (2020). A Hybrid Nanomaterial Based on Single Walled Carbon Nanotubes Cross-Linked via Axially Substituted Silicon (IV) Phthalocyanine for Chemiresistive Sensors. Molecules, 25(9), 2073.
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5

Synthesis and Purification of Organometallic Compounds

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Solvents of p.a. quality (per analysis) were commercially acquired from Sigma Aldrich, Carl Roth, or Acros Fisher Scientific and unless otherwise stated, used without further purification. Anhydrous solvents were purchased from Carl Roth, Acros, or Sigma Aldrich (less than 50 ppm of H2O, kept over molecular sieves). 2-Bromo-6-methylpyridine (98%) and benzyl azide (94%) were bought from Alfa Aesar. Propargyl alcohol (98%), butynyl alcohol (97%), bis(triphenylphosphine)palladium(II) dichloride (98%), and chloro­(pentamethylcyclopentadienyl)(cyclooctadiene)ruthenium(II) (99.5%) were purchased from Sigma Aldrich.
Reaction mixtures were purified by flash chromatography. For the stationary phase of the column, silica gel, produced by Merck (silica gel 60, 0.040 × 0.063 mm, 260–400 mesh ASTM) and sea sand by Riedel de Haën (baked out and washed with hydrochloric acid) were used.
Air- and moisture-sensitive reactions were carried out under argon atmosphere in previously baked out apparatuses with standard Schlenk techniques. Liquid reagents and solvents were injected with syringes and stainless-steel cannulas of different sizes.
Ferrari F., Braun J., Anson C.E., Wilts B.D., Moatsou D, & Bizzarri C. (2021). Cyan-Emitting Cu(I) Complexes and Their Luminescent Metallopolymers. Molecules, 26(9), 2567.
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6

Synthesis of Gold Nanoparticles with Silane Functionalization

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HAuCl4 (Johnson Matthey, Assay
41.79 wt %), sodium citrate dehydrate (Sigma-Aldrich, >99%), (3-aminopropyl)trimethoxysilane
(APTMS, Alfa Aesar, 97%), sodium silicate (Sigma-Aldrich, reagent
grade), H2SO4 (BDH, Aristar grade), perchloric
acid (BDH, Aristar grade), propargyl alcohol (Sigma-Aldrich, 99%),
and 2-methyl-3-butyn-2-ol (Alfa Aesar, 98%) were used as received
and all aqueous solutions were prepared using ultrapure water (18.2
MΩ cm).
Guan S., Attard G.A, & Wain A.J. (2020). Observation of Substituent Effects in the Electrochemical Adsorption and Hydrogenation of Alkynes on Pt{hkl} Using SHINERS. ACS Catalysis, 10(19), 10999-11010.
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7

Synthesis of Fluorescent Lactose Derivatives

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All reagents were obtained from commercial sources. D-lactose, acetic anhydride, N,N-dimethylformamide (DMF), trichloroacetonitrile, 1,8-diazabicyclo [5.4.0]undec-7-ene (DBU), boron trifluoride diethyl etherate (BF3·Et2O), propargyl alcohol, sodium metal, Dowex-50 resin (H+ form), 5-bromovaleryl chloride, 2,4-dimethyl pyrrole, triethylamine (TEA), N-iodosuccimide (NIS) were purchased from Sigma Aldrich (St. Louis, MO, USA). Sodium azide, sodium ascorbate, copper (II) sulfate pentahydrate, sodium hydroxide (NaOH), sulfuric acid (H2SO4), sodium hydrogen carbonate (NaHCO3), magnesium sulfate (MgSO4), and ammonium carbonate [(NH4)2CO3] were procured from Daejung Chemical (Gyeonggi-do, South Korea) and used without further purification. Ethyl acetate (EtOAc), dichloromethane (CH2Cl2), tetrahydrofuran (THF), methanol, and other solvents were of analytical grade and were dried under calcium hydride prior to use, except THF.
All compounds were characterized by 1H- and 13C-NMR spectroscopy on a Bruker AM 250 spectrometer (Billerica, MA, USA) and high-resolution electrospray ionization mass spectrometry (HR-ESI-MS) on a SYNAPT G2-Si high definition mass spectrometer (Waters, London, United Kingdom).
Khuong Mai D., Kang B., Pegarro Vales T., Badon I.W., Cho S., Lee J., Kim E, & Kim H.J. (2020). Synthesis and Photophysical Properties of Tumor-Targeted Water-Soluble BODIPY Photosensitizers for Photodynamic Therapy. Molecules, 25(15), 3340.
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8

Boronic Acid-Mediated Biomolecule Conjugation

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Citric acid, ethylenediamine, 4-aminophenylboronic acid, phenylboronic acid,
poly(ethylene glycol) (PEG600, molecular weight 570–630),
N-(3-(dimethylamino)propyl)-N′-ethylcarbodimide
hydrochloride (EDC), N-hydroxysuccinimide (NHS), propargyl alcohol,
4-pentynoic acid, copper sulfate pentahydrate, l-ascorbic acid, and sodium
hydroxide were purchased from Sigma-Aldrich. The dialysis membranes were supplied by
Spectrum Laboratories.
Łoczechin A., Séron K., Barras A., Giovanelli E., Belouzard S., Chen Y.T., Metzler-Nolte N., Boukherroub R., Dubuisson J, & Szunerits S. (2019). Functional Carbon Quantum Dots as Medical Countermeasures to Human Coronavirus. ACS Applied Materials & Interfaces, 11(46), 42964-42974.
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9

Synthesis and Characterization of Functional Polymers

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Methyl methacrylate, glycidyl methacrylate, oligo(ethylene glycol) methyl ether methacrylate (OEGMA), 4-cyano-4(phenylcarbonothioylthio) pentanoic acid (CPADB) (>97%), azobisisobutyronitrile (AIBN), propargyl alcohol, sodium azide, N,N’-dicyclohexylcarbodiimide, 4-dimethylaminopyridine, copper(I)bromide, N,N,N′,N′′,N′′-pentamethyldiethylenetriamine (PMDETA), ammonium chloride, ammonia solution (25%), toluene, methanol, methylene chloride, diethyl ether, tetrahydrofuran, N,N-dimethylformamide, dimethyl sulfoxide, choloroform, and neutral alumina were purchased from Sigma-Aldrich and were used as received. NMR solvents CDCl3 and DMSO-d6 were purchased from Eurisotop, Saint Aubin, France.
Thankappan H., Semsarilar M., Li S., Chang Y., Bouyer D, & Quemener D. (2020). Synthesis of Block Copolymer Brush by RAFT and Click Chemistry and Its Self-Assembly as a Thin Film. Molecules, 25(20), 4774.
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10

Click Chemistry Reagents for Bioconjugation

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HEPES (Sigma-Aldrich, 99.5% purity, copper ≤ 5 ppm); MgCl2.H2O (Sigma-Aldrich, 99% purity, copper ≤ 5 ppm); LiOH·H2O (Sigma-Aldrich, ≥ 99% purity, copper ≤ 5 ppm); sodium ascorbate (Sigma-Aldrich, 98% purity); NaCl (Sigma-Aldrich, 99% purity); KCl (ACP Chemicals, 99%); sodium acetate (Bio Basic, 99% purity); 5-hexyn-1-ol (Sigma-Aldrich, 96% purity); propargyl alcohol (Sigma-Aldrich, 99% purity); 3-azido-7-hydroxycoumarin (AK Scientific 98% purity); azide-PEG3-biotin conjugate (Sigma-Aldrich, purity not specified by the manufacturer); NaOH (Sigma-Aldrich, 99% purity); CuSO4 (Fisher Scientific, 99% purity); Azido-PEG2-NHS ester (BroadPharm, 98% purity); Fluorescein-NHS ester (BroadPharm, 95% purity); AFDye 546 (Click Chemistry Tools, ≥95%); Lysozyme, from chicken egg white (Sigma-Aldrich, ≥ 98% purity); Nuclease P1 (NEB, 100,000 Units/mL).
Liu K., Lat P.K., Yu H.Z, & Sen D. (2020). CLICK-17, a DNA enzyme that harnesses ultra-low concentrations of either Cu+ or Cu2+ to catalyze the azide-alkyne ‘click’ reaction in water. Nucleic Acids Research, 48(13), 7356-7370.
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