Phenylacetylene

Manufactured by Merck Group

Sourced in United Kingdom, United States

Phenylacetylene is a chemical compound that consists of a phenyl group (C6H5-) and an acetylene group (-C≡CH). It is a colorless liquid with a characteristic odor. Phenylacetylene is commonly used as a precursor in organic synthesis and as a building block for various chemical products.

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Lab products found in correlation

Propargyl alcohol, by Merck Group (3 mentions) N bu4sn, by Fujifilm (2 mentions) Iodobenzene, by Merck Group (2 mentions) Hexane, by Merck Group (2 mentions) Chloroform, by Merck Group (2 mentions) Ethanol, by Merck Group (2 mentions) Benzyl bromide, by Merck Group (2 mentions) Ethylene glycol, by Merck Group (2 mentions) Aniline, by Merck Group (2 mentions) Dpx 400 mhz spectrometer, by Bruker (1 mentions) Phenol, by Merck Group (1 mentions) Propargylamine, by Merck Group (1 mentions) Propargyl acrylate, by Merck Group (1 mentions) Red phosphorus, by Thermo Fisher Scientific (1 mentions) Pmdeta, by Merck Group (1 mentions) Dimethyl sulfoxide (dmso), by Merck Group (1 mentions) ε caprolactone, by Merck Group (1 mentions) Chloroform, by Fujifilm (1 mentions) Trifluoroacetic acid, by Fujifilm (1 mentions) Dimethyl sulfoxide (dmso), by Fujifilm (1 mentions)

12 protocols using phenylacetylene

Synthesis and Characterization of Air-Sensitive Organometallics

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All reactions
were carried out using standard Schlenk and glovebox techniques under
an inert atmosphere of argon. Solvents (THF, hexane, benzene, and
toluene) were dried by heating to reflux over sodium benzophenone
ketyl and distilled under nitrogen prior to use. NMR spectra were
recorded on a Bruker DPX 400 MHz spectrometer, operating at 400.13
MHz for ¹H and 100.62 MHz for ¹³C{¹H}. 1-Methylbenzimidazole, phenylacetylene, phenol, and diphenylamine
were purchased from Sigma-Aldrich Chemicals or Alfa Aesar and used
as received. 2-Picoline was dried by heating to reflux over calcium
hydride, distilled under nitrogen, and stored over activated 4 Å
molecular sieves prior to use. [Ga(CH₂SiMe₃)₃],^{51 (link)} I^tBu,^{52 (link)} and LiTMP^{53 (link)} were prepared according to literature methods and stored and handled
under an inert atmosphere because of their air sensitivity (I^tBu) and pyrophoricity (Ga(CH₂SiMe₃)₃ and LiTMP).

Uzelac M., Kennedy A.R, & Hevia E. (2017). Trans-Metal-Trapping Meets Frustrated-Lewis-Pair Chemistry: Ga(CH2SiMe3)3-Induced C–H Functionalizations. Inorganic Chemistry, 56(15), 8615-8626.

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Synthesis of Black Phosphorus from Red Phosphorus

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Red phosphorus (98.9%), tin (99.5%), and tin(IV) iodide (95%) were purchased from Alfa Aesar. Ethyl alcohol (absolute) was obtained from Sigma-Aldrich. Dimethyl sulfoxide (DMSO) was purchased from Merck. All chemicals and solvents were used as received without further purification for synthesis of black phosphorus. Benzyl bromide (Merck), phenylacetylene (Sigma), propargylamine (Sigma), propargyl alcohol (Sigma), d-Dimethyl sulfoxide, (DMSO-d₆, Merck), N,N,N’,N’’,N’’-pentamethyldiethylenetriamine (PMDETA, Aldrich), sodium azide (NaN₃, Panreac), copper(II) chloride (Cu^IICl₂, Merck), black phosphorus, Dimethyl sulfoxide (DMSO) was used as received. Propargyl acrylate (Sigma), styrene (Merck) were purified before by using a basic alumina column to remove the inhibitor and then stored in the fridge. ε-Caprolactone (Merck), and stannous octoate (Aldrich) were dried with CaH₂ under vacuum.

Kocaarslan A., Eroglu Z., Metin Ö, & Yagci Y. (2021). Exfoliated black phosphorous-mediated CuAAC chemistry for organic and macromolecular synthesis under white LED and near-IR irradiation. Beilstein Journal of Organic Chemistry, 17, 2477-2487.

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Synthesis of Functionalized Alkyne Monomers

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Bis(triphenylphosphine)palladium(ii) dichloride, triphenylphosphine, copper(i) iodide, 1-bromo-4-tert-butylbenzene, 1,4-dibromobenzene, sodium hydride, iodomethane, 2-methyl-3-butyn-2-ol, tetrahydrofuran (THF), triethylamine, N,N-dimethylformamide (DMF), chloroform (CHCl₃), methanol (MeOH), trifluoroacetic acid (TFA), dimethyl sulfoxide (DMSO) (Fujifilm Wako Pure Chemical (Wako)), chlorotrimethylsilane (Tokyo Chemical Industry), n-butyllithium (Kanto Chemical), tantalum(v) chloride, and phenylacetylene (Sigma-Aldrich) were used without additional purification. n-Bu₄Sn (cocatalyst for polymerization, Wako) and toluene (solvent for polymerization, Wako) were distilled over CaH₂ (Wako) prior to use. 1-(p-Trimethylsilyl)phenyl-1-propyne (SPP),^{21 (link)} 4-(tert-butyl)diphenylacetylene (BDPA),^{10 (link)} and 4-(trimethylsilyl)diphenylacetylene (SDPA)^{11 (link)} were prepared according to the literature.

Lin Y., Dong J., Sakaguchi T, & Hashimoto T. (2021). Development of highly gas-permeable polymers by metathesis copolymerization of 1-(p-trimethylsilyl)phenyl-1-propyne with tert-butyl and silyl group-containing diphenylacetylenes. RSC Advances, 11(51), 32419-32424.

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Characterization of Linear 1-Alkynes

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Phenylacetylene (98%) and propyne, 1-pentyne, 1-hexyne, 1-heptyne, and 1-octyne (C₃, C₅, C₆, C₇, and C₈ linear 1-alkynes, respectively, ≥97%) were obtained from Sigma-Aldrich. 1-Butyne was supplied by Apollo Gases Ltd. Acetylene was obtained from BOC, a member of the Linde Group. Protein concentrations were determined using a Pierce bicinchoninic acid (BCA) protein assay kit (Thermo Scientific) as described by the manufacturer.

Wright C.L., Schatteman A., Crombie A.T., Murrell J.C, & Lehtovirta-Morley L.E. (2020). Inhibition of Ammonia Monooxygenase from Ammonia-Oxidizing Archaea by Linear and Aromatic Alkynes. Applied and Environmental Microbiology, 86(9), e02388-19.

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Preparation of Silane-Containing Block Copolymer Micelles

Cited 1 time

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Titanium chloride (TiCl₄), titanium tetraisopropoxide (TIPO), 1,4-dioxane, phenylacetylene, commercial Pt/C (5 wt%) and platinum acetylacetonate (Pt(acac)₂) were purchased from Sigma-Aldrich. The CDCl₃ was purchased from Cambridge Isotope Laboratories, Inc. All the chemicals were used without further purification unless otherwise noted. Silane-containing block copolymers of poly(ethylene oxide)-block-poly(3-(trimethoxysilyl)propyl methacrylate) (PEO-b-PTMSPMA, M_n = 56.9 kg mol⁻¹) was prepared through atom transfer radical polymerization (ATPR) method as described in our previous reports (Tauster et al., 1978 (link); Wang et al., 2015 (link); Zhang et al., 2015 (link); Feng et al., 2017 (link); Hu et al., 2020 (link)). The polymer micelles were prepared in water/ethanol mixtures and dialyzed in ethanol prior to use. Deionized water (High-Q, Inc. 103S Stills) with a resistivity of >10.0 MΩ was used in all experiments.

Hu M., Jin L., Dang Y., Suib S.L., He J, & Liu B. (2020). Supported Pt Nanoparticles on Mesoporous Titania for Selective Hydrogenation of Phenylacetylene. Frontiers in Chemistry, 8, 581512.

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Synthesis of Substituted Phenylacetylenes

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The polymerization solvent, toluene (Fujifilm Wako Pure Chemical Co., Ltd., Osaka, Japan), was purified twice by distillation in the presence of CaH₂ (Fujifilm Wako Pure Chemical Co., Ltd.). The main catalyst, TaCl₅ (99.999%, Sigma-Aldrich, St. Louis, Missouri, USA), was used without further purification, while the cocatalyst, n-Bu₄Sn (Fujifilm Wako Pure Chemical Co., Ltd.), was used after distillation in the presence of CaH₂. Phenylacetylene (Sigma-Aldrich), 1,4-dibromobenzene, 1-bromo-4-tert-butylbenzene, triethylamine, triphenylphosphine, copper(i) iodide, dichlorobis(triphenylphosphine)palladium(ii), n-butyllithium, trifluoroacetic acid (TFA), chlorotrimethylsilane, 2-methyl-3-butyn-2-ol, sodium hydride, aqueous sodium nitrate, and other common solvents (Fujifilm Wako Pure Chemical Co., Ltd.) were used without further purification. 1-(p-Trimethylsilyl)phenyl-2-(p-trimethylsilyl)Phenylacetylene (1a),^{23 (link)} 1-phenyl-2-(p-tert-butyl)Phenylacetylene (1b),^{11 (link)} and 1-phenyl-2-(p-trimethylsilyl)Phenylacetylene (1c)^{10 (link)} were synthesized according to the methods reported in literature.

Lin Y., Sakaguchi T, & Hashimoto T. (2020). Desilylation of copolymer membranes composed of poly[1-(p-trimethylsilyl)phenyl-2-(p-trimethylsilyl)phenylacetylene] for improved gas permeability. RSC Advances, 10(25), 14637-14643.

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Metal Oxide Synthesis and Characterization

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Iron (III) nitrate nonahydrate
(Fe(NO₃)₃·9H₂O), iron (II) sulfate
heptahydrate (FeSO₄·7H₂O), acetone, hexane,
nitric acid (64–66%, HNO₃), sodium hydroxide (NaOH),
iodobenzene, phenylacetylene, potassium carbonate, indigo carmine,
and ethylene glycol were all purchased from Sigma-Aldrich (Dorset,
U.K.). Methylene blue trihydrate was purchased from Bio Basic (Cambridgeshire,
U.K.). Deionized water was obtained from a Suez L300130 (>1 MΩ
cm). Carbon dioxide (N5.0, BOC) and helium (A Grade, 99.996%, BOC)
were supplied by BOC. Iron (II, III) oxide (97%, metals basis) was
purchased from Alfa Aesar (Lancashire, U.K.). All materials were used
as received unless otherwise stated.

Davies G, & McGregor J. (2021). Hydrothermal Synthesis of Biomass-Derived Magnetic Carbon Composites for Adsorption and Catalysis. ACS Omega, 6(48), 33000-33009.

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Synthesis of Polymer Brushes on Ti6Al4V

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Methacryloyl chloride (97 %), 4-methylphenol (99 %), propargyl alcohol (99 %), phenylacetylene (98 %), ethyl α-bromoisobutyrate (EBiB, 98 %), α-bromoisobutyryl bromide (BiBB, 98 %), 2, 2′-bipyridyl (BPY, 97 %), copper(I) bromide (CuBr, 99.999 %), sodium azide (99.5 %), trifluoroethanol (TFE, 99 %), benzene (99.8 %) and dimethylformamide (DMF, 99.5 %) were purchased from Sigma-Aldrich (St. Louis, MO, USA) and used as received. Diethyl (hydroxymethyl)phosphonate (P-OH, 98 %) and 2-(2-(2-Chloroethyoxy)ethoxy)-ethanol (TEG-Cl, 96 %) were purchased from TCI America (Portland, OR, USA) and used as received. Triethylamine (TEA, 99.5 %, Sigma-Aldrich) was dried by calcium hydride (CaH₂, 99.99 %, Sigma-Aldrich) and distilled prior to use. Ti6Al4V plates (1.3 mm thick, Titanium Metal Supply Inc., Poway, CA, USA) was cut into 10 × 10 mm² square pieces, which were sequentially polished under water with 600, 1500, and 3000 grit silicon carbide sandpapers and ultrasonically cleaned with hexane (10 min), DCM (10 min), and acetone (10 min) prior to use.

Liu P, & Song J. (2015). Well-controlled ATRP of 2-(2-(2-Azidoethyoxy)ethoxy)ethyl Methacrylate for High-density Click Functionalization of Polymers and Metallic Substrates. Journal of polymer science. Part A, Polymer chemistry, 54(9), 1268-1277.

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Copper-Catalyzed Azide-Alkyne Cycloaddition

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Aniline, iodobenzene, bromobenzene, chlorobenzene, 3-iodopropyltrimethoxysilane, benzyl bromide, phenylacetylene, NaN₃, CuCl₂·2H₂O, CuI, NaBH₄, MgSO₄, and BMI·BF₄ were purchased from Sigma-Aldrich. All chemicals were used without further purification, except for DCM, toluene, MeOH, acetonitrile, Et₂O, and EtOAc, which were purified by standard procedures.²⁴

Valdebenito C., Pinto J., Nazarkovsky M., Chacón G., Martínez-Ferraté O., Wrighton-Araneda K., Cortés-Arriagada D., Camarada M.B., Alves Fernandes J, & Abarca G. (2020). Highly modulated supported triazolium-based ionic liquids: direct control of the electronic environment on Cu nanoparticles. Nanoscale Advances, 2(3), 1325-1332.

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Synthesis of Nanomaterials Using Diverse Chemicals

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Acetone, hydrazine hydrated (N₂H₄·H₂O), polyvinylpyrrolidone (PVP), sodium hydroxide (NaOH), sodium nitrate, sulphuric acid (H₂SO₄), hydrochloric acid (HCl), sodium nitrate (NaNO₃), 4-nitrophenol (4-NP), and nickel(ii)nitrate hexahydrate (Ni(NO₃)₂·6H₂O) were purchased from Fischer Scientific. Silver nitrate (AgNO₃), potassium permanganate (KMnO₄), sodium azide (NaN₃), 30% H₂O₂ solution, ethylene glycol, acetonitrile, methanol, dichloromethane, toluene, chloroform, diethylamine, and aniline were purchased from Merck, India. Sodium borohydride (NaBH₄), aldehydes, piperidine, phenylacetylene, styrene, styrene oxide, cyclohexene oxide, epichlorohydrin, tert-butyl hydroperoxide (TBHP in 5–6 M decane), and graphite powder (mean particle size of <20 mm) were purchased from Sigma-Aldrich. All the chemicals were used without further purification. Distilled water was used throughout the experiment.

Chandel M., Makkar P., Ghosh B.K., Moitra D, & Ghosh N.N. (2018). A facile synthesis methodology for preparation of Ag–Ni-reduced graphene oxide: a magnetically separable versatile nanocatalyst for multiple organic reactions and density functional study of its electronic structures. RSC Advances, 8(66), 37774-37788.

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