Phenylacetylene

Base Information

• Chemical Name: Phenylacetylene
• CAS No.: 536-74-3
• Deprecated CAS: 1401716-44-6
• Molecular Formula: C8H6
• Molecular Weight: 102.136
• Hs Code.: 2902 90 00
• European Community (EC) Number: 208-645-1
• NSC Number: 4957
• UNII: 239WSR2IBO
• DSSTox Substance ID: DTXSID1060211
• Nikkaji Number: J24.280B,J2.700.985I
• Wikipedia: Phenylacetylene
• Wikidata: Q417321
• ChEMBL ID: CHEMBL234833
• Mol file: 536-74-3.mol

Synonyms:1-Phenylethyne;Ethyne, phenyl-;NSC 4957;Ethynylbenzene;Phenylethyne;

Chemical Property of Phenylacetylene

Chemical Property:

• Appearance/Colour: colourless liquid
• Vapor Pressure: 17.6 mm Hg ( 37.7 °C)
• Melting Point: - 44.8 °C
• Refractive Index: n20/D 1.549(lit.)
• Boiling Point: 142.4 °C at 760 mmHg
• PKA: 19(at 25℃)
• Flash Point: 31.111 °C
• PSA: 0.00000
• Density: 0.951 g/cm³
• LogP: 1.66790
• Storage Temp.: 2-8°C
• Sensitive.: Light Sensitive
• Solubility.: H2O: insoluble
• Water Solubility.: INSOLUBLE
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 102.0469501914
• Heavy Atom Count: 8
• Complexity: 98.5

Purity/Quality:

99.5% ^*data from raw suppliers

Phenylacetylene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 10-36/37/38-40-65-36/37
• Safety Statements: 16-26-36/37/39-45-62-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Aromatic Hydrocarbons
• Canonical SMILES: C#CC1=CC=CC=C1
• Description: Phenylacetylene is an alkyne hydrocarbon containing a phenyl group. It exists as a colorless, viscous liquid. In research, it is sometimes used as an analog for acetylene; being a liquid, it is easier to handle than acetylene gas.Phenylacetylene undergoes polymerization catalyzed by Rh and Pt complexes to form polyphenylacetylene.
• Uses: Ethynylbenzene, an aromatic hydrocarbon, is important in the petrochemical industry as an intermediate in the production of styrene, which in turn is used for making polystyrene, a common plastic mate rial. Phenylacetylene is involved in the preparation of styrene by reduction using Lindlar catalyst. It is used to study the mechanism of the palladium-catalyzed phenyl acetylene oxidative carbonylation reaction. It is also used in the polymerization process to prepare polyphenylacetylene namely 1,2,4-triphenylbenzene and 1,3,5-triphenylbenzene. Terminal acetylene used in the conversion of nitrones to alkynyl hydroxyl amines in the presence of trimethylaluminum..

Technology Process of Phenylacetylene

There total 490 articles about Phenylacetylene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 55.0%

<4>Radialene (3227-91-6) → styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) + o-xylene (95-47-6) + phenylacetylene (536-74-3) + toluene (108-88-3,15644-74-3,16713-13-6) + benzene (71-43-2,26181-88-4,54682-86-9,13967-78-7,174973-66-1)

Guidance literature:

at 880 ℃; under 0.001 Torr;

Reference yield: 40.0%

bromostyrene (103-64-0,1340-14-3) → styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) + 2,5-Diphenyl-thiophene (1445-78-9) + 2-phenylnaphthalene (612-94-2) + phenylacetylene (536-74-3)

Guidance literature:

With hydrogen sulfide; at 160 ℃; for 4h;

Reference yield: 20.0%

2,2,2-trichloroethylbenzene (3883-13-4) → styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) + (Z)-β-chlorostyrene (4604-28-8) + phenylacetylene (536-74-3)

Guidance literature:

2,2,2-trichloroethylbenzene; With chromium dichloride; at 20 ℃; for 4h;

With Dipropyl disulfide; at 20 ℃; for 0.5h;

at 120 ℃; for 12h; Further stages.;

DOI:10.1021/ja016515n

upstream raw materials:

styrene

Phenylpropargyl aldehyde

n-butyllithium

diethyl ether

Downstream raw materials:

3,5-diphehylisoxazole

1,2,4-triphenylbenzene

1’-(4-phenyl-[1,2,3]-triazol-1-yl)-2’,3’,4’,6’-tetra-O-acetyl-β-D-glucopyranose

ethyl 5-phenylpyrazole-3-carboxylate

Refernces

• 1、 Gao, Fei,Lin, Cong,Lin, Jingyi,Shen, Liang,Teng, Qiuxun,Xu, Yiqing. "Nickel-Catalyzed Annulation of Aliphatic Amides with Alkynyla silanes: An Expeditious Approach to Five-Membered Lactams". . p. 889 - 894. Retrieved 2020.
• 2、 Holleman. "-". . p. 3081. Retrieved 1887.
• 3、 Stearns, Jaime A.,Zwier, Timothy S.,Kraka, Elfriede,Cremer, Dieter. "Experimental and computational study of the ultraviolet photolysis of vinylacetylene. Part II". . p. 5317 - 5327. Retrieved 2006.
• 4、 Li, Minyan,Gutierrez, Osvaldo,Berritt, Simon,Pascual-Escudero, Ana,Ye?l?imen, Ahmet,Yang, Xiaodong,Adrio, Javier,Huang, Georgia,Nakamaru-Ogiso, Eiko,Kozlowski, Marisa C.,Walsh, Patrick J.. "Transition-metal-free chemo- and regioselective vinylation of azaallyls". . p. 997 - 1004. Retrieved 2017.
• 5、 Wondergem, Caterina S.,Hartman, Thomas,Weckhuysen, Bert M.. "In Situ Shell-Isolated Nanoparticle-Enhanced Raman Spectroscopy to Unravel Sequential Hydrogenation of Phenylacetylene over Platinum Nanoparticles". . p. 10794 - 10802. Retrieved 2019.
• 6、 Okamoto, Sentaro,Ono, Naoya,Tani, Kousuke,Yoshida, Yukio,Sato, Fumie. "Conversion of Allyl Alk-2-ynoates to Alk-2-ynoic Acids Using Morpholine and Palladium(0)-Bis(diphenylphosphino)alkane Catalyst; Synthesis of 2,2,3,3-Tetradehydro PGE1". . p. 279 - 280. Retrieved 1994.
• 7、 Ustynyuk, N. A.,Vinogradova, V. N.,Korneva, V. N.,Kravtsov, D. N.,Andrianov, V. G.,Struchkov, Yu. T.. "THERMAL DECOMPOSITION OF (η-CYCLOPENTADIENYL)TRICARBONYL(?-PHENYLETHYNYL)MOLYBDENUM AND THE MOLECULAR STRUCTURE OF A MOLYBDENUM BINUCLEAR COMPLEX WITH A BRIDGING 1,4-DIPHENYLBUTADIYNE LIGAND 2(μ-1,2-η-C6H5CC-CCC6H5)". . p. 285 - 296. Retrieved 1984.
• 8、 Tenorio, Manuel Jimenez,Puerta, M. Carmen,Valerga, Pedro. "Ruthenium-Dihydrogen Complexes via C-H Cleavage in Alk-1-ynes. Crystal Structure of CPh)(dippe)2> ". . p. 1750 - 1751. Retrieved 1993.
• 9、 Bianchini, Claudio,Mealli, Carlo,Peruzzini, Maurizio,Vizza, Francesco,Zanobini, Fabrizio. "Activation of C-H bonds in acetylene and terminal alkynes by rhodium(I) species. Crystal structure of cis-(ethynyl)hydrie BPh4.1.5C4H8O (NP3 = N(CH2CH2PPh2)3)". . p. C53 - C57. Retrieved 1988.
• 10、 -. "Green method for solvent-free synthesis of MDPES raw material phenylacetylene". Paragraph 0034-0041. . Retrieved 2021/04/07.