Phenylacetylene

Manufactured by Thermo Fisher Scientific

Sourced in Germany

Phenylacetylene is a chemical compound with the formula C₆H₅C≡CH. It is a colorless, flammable liquid with a characteristic odor. Phenylacetylene is used as a precursor in the synthesis of various organic compounds.

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6 protocols using phenylacetylene

Pd-Catalyzed Hydrogenation of Unsaturated Compounds

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Pd microencapsulated
in polyurea (Pd Encat
30, 0.4 mmol/g Pd loading, Sigma-Aldrich) was used as hydrogenation
catalyst. Chloroform was obtained from Fisher Scientific. Cyclohexene
and phenylacetylene were obtained from Alfa Aesar. Styrene and hex-5-en-2-one
from Sigma-Aldrich and hydrogen gas from Linde Gas. All chemicals
were used as received and none of the solvents were degassed.

Tijssen K.C., van Weerdenburg B.J., Zhang H., Janssen J.W., Feiters M.C., van Bentum P.J, & Kentgens A.P. (2019). Monitoring Heterogeneously Catalyzed Hydrogenation Reactions at Elevated Pressures Using In-Line Flow NMR. Analytical Chemistry, 91(20), 12636-12643.

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Synthesis of Carbonaceous Materials

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d-Glucose, active carbon (AC), concentrated nitric acid (65–68%) and concentrated sulfuric acid (98%) were purchased from Sinopharm Chemical Reagent Co., Ltd. Phenylacetylene (PA) was purchased from Alfa Aesar. Carbon nanotubes (CNTs) were provided by Shandong Dazhan Nano Materials Co., Ltd. The ordered mesoporous carbon (CMK) was purchased from Nanjing Ji Cang Nano Tech Co., Ltd.

Yan P., Xie Z., Tian S., Li F., Wang D., Su D.S, & Qi W. (2018). Hydration of phenylacetylene on sulfonated carbon materials: active site and intrinsic catalytic activity. RSC Advances, 8(67), 38150-38156.

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Organometallic Synthesis Procedures

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Mercury(ii) acetate was purchased from Sigma-Aldrich Co. Ltd. Potassium tetrachoroaurate(iii) was purchased from ChemPur. Phenylacetylene was purchased from Acros Organics. Tetrahydrofuran and dichloromethane for the reactions were purified using an Innovative Technology, Inc. PureSolv MD 5 Solvent Purification System before use. All of the other solvents and commercially available reagents were of analytical grade and were used as received. Tetra(n-butyl)-ammonium hexafluorophosphate (Aldrich) was recrystallized three times from absolute ethanol before use. All of the reactions were performed under inert and anhydrous conditions using standard Schlenk techniques unless otherwise specified.

Wong B.Y., Wong H.L., Wong Y.C., Au V.K., Chan M.Y, & Yam V.W. (2017). Multi-functional bis(alkynyl)gold(iii) N⁁C complexes with distinct mechanochromic luminescence and electroluminescence properties †Electronic supplementary information (ESI) available: CCDC 1552808. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c7sc02410j. Chemical Science, 8(10), 6936-6946.

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Purification of Organic Solvents and Reagents

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Toluene and dichloromethane (DCM) were distilled under normal pressure over calcium hydride under nitrogen before use. Tetrahydrofuran (THF) was distilled under normal pressure from sodium benzophenone ketyl under nitrogen immediately prior to use. Triethylamine (Et₃N) was distilled and dried over potassium hydroxide. Other solvents, including N,N-dimethyl- formamide (DMF), chloroform (CHCl₃), methanol, ethyl acetate, hexane and petroleum ether (PE, b. p. 60–90 °C) were purchased from Sinopharm Co. Ltd (Hangzhou, China). They were of analytical grade and directly used as received without further purification. WCl₆, Ph₄Sn, CuI, PPh₃ and [PdCl₂⋅(PPh₃)₂] were bought from Aldrich (Shanghai, China). N,N′-dicyclohexylcarbodiimide (DCC), p-toluene sulfonic acid monohydrate (TsOH), 4-(dimethylamino)pyridine (DMAP), phenylacetylene, pyrene-methylamine, and pentafluorophenol were purchased from Acros (Shanghai, Chnia). Methyl 6-(4-iodo-phenoxy)hexanoate was obtained accroding to the procedures reported elsewhere [37 (link)].

Shen T., Jiang N., Zhang X., He L., Lang X.H., Sun J.Z, & Zhao H. (2019). Pyrene-Functionalized Polyacetylenes: Synthesis and Photoluminescence Property. Polymers, 11(8), 1366.

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Synthesis and Characterization of Organometallic Compounds

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All reagents were used as received from the
following suppliers. 1-Bromooctane (C₈H₁₇Br),
1-bromododecane (C₁₂H₂₄Br), sodium thiosulfate
pentahydrate (Na₂O₃S₂·5H₂O), and hydrogen hexachloroplatinate (IV) hydrate (H₂PtCl₆) were obtained from Sigma-Aldrich. Tetra-n-octylammonium bromide (TOAB), 1-octanethiol, sodium borohydride
(NaBH₄), potassium tetrachloroplatinate(II) (K₂PtCl₄), phenylacetylene, diphenylacetylene, tert-butyl propiolate, 3,3-dimethyl-1-butyne, methyl propiolate, 3-butyn-2-one,
2-methyl-3-butyn-2-ol, 1-pentyne, and dimethyl acetylenedicarboxylate
(DMAD) were obtained from Acros. Ethanol, mEthanol, acetone, dichloromethane
(DCM), and toluene (tol) were obtained from Fisher Scientific. Deuterium
oxide (D₂O), chloroform-d (CDCl₃), dichloromethane-d₂ (CD₂Cl₂), mEthanol-d₄ (CD₃OD), and toluene-d₈ were purchased
from Cambridge Isotope Laboratories, Inc.

San K.A., Chen V, & Shon Y.S. (2017). Preparation of Partially Poisoned Alkanethiolate-Capped Platinum Nanoparticles for Hydrogenation of Activated Terminal Alkynes. ACS Applied Materials & Interfaces, 9(11), 9823-9832.

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Synthesis of Substituted Benzenes

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Tetraphenylmethane (95%, ABCR, Karlsruhe, Germany), 1,3,5-tribromobenzene (98%, Acros Organics, Geel, Belgium), bromine (99%, Acros Organics, Geel, Belgium) trimethylsilylacetylene (98%, ABCR, Karlsruhe, Germany), CuBr (98%, Sigma-Aldrich, Darmstadt, Germany), CuI (98%, Fluka, Dresden, Germany), tetrakis(triphenylphosphine)palladium(0) (99%, Sigma-Aldrich, Darmstadt, Germany), bis(triphenylphosphine)palladium(II) dichloride (98%, Sigma-Aldrich, Darmstadt, Germany), Bu4NF (1M solution in THF, ABCR, Karlsruhe, Germany), bis(4-bromophenyl)ether (99%, Sigma-Aldrich, Darmstadt, Germany), 1,4-diiodobenzene (98%, ABCR, Karlsruhe, Germany), phenylacetylene (98%, Acros Organics, Geel, Belgium), 1,3-diphenyl-2-propanone (99%, Sigma-Aldrich, Darmstadt, Germany), potassium hydroxide (99%, Acros Organics, Geel, Belgium), glacial acetic acid (99%, Sigma-Aldrich, Darmstadt, Germany), potassium permanganate, triethylamine (99%, Acros Organics, Geel, Belgium), toluene (99.5%, Component Reactive, Moscow, Russia), ethanol (96%, Component Reactive, Moscow, Russia), diphenylether (99%, ABCR, Karlsruhe, Germany), THF ( HPLC grade, Carlo Erba reagents, Milan, Italy), and gases: N₂ (99.999%) and CO₂ (99.999%) were used as received.

Sorokina S.A., Kuchkina N.V., Mikhalchenko A.V., Krasnova I.Y., Khanin D.A., Skupov K.M, & Shifrina Z.B. (2023). Ultramicroporous Polyphenylenes via Diels–Alder Polycondensation Approach. Polymers, 15(9), 2060.

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