Diphenylacetylene

Base Information

• Chemical Name: Diphenylacetylene
• CAS No.: 501-65-5
• Deprecated CAS: 72234-42-5
• Molecular Formula: C14H10
• Molecular Weight: 178.233
• Hs Code.: 29029090
• European Community (EC) Number: 207-926-6
• NSC Number: 5185
• UNII: Y70JA8HB75
• DSSTox Substance ID: DTXSID4060109
• Nikkaji Number: J6.193J
• Wikipedia: Diphenylacetylene
• Wikidata: Q902100
• Pharos Ligand ID: A2QVTMB463W7
• Metabolomics Workbench ID: 57790
• ChEMBL ID: CHEMBL223309
• Mol file: 501-65-5.mol

Synonyms:biphenylacetylene;diphenylacetylene

Chemical Property of Diphenylacetylene

Chemical Property:

• Appearance/Colour: white crystals
• Melting Point: 59-61 °C
• Refractive Index: 1.6415 (estimate)
• Boiling Point: 300 °C at 760 mmHg
• Flash Point: 126.043 °C
• PSA: 0.00000
• Density: 1.069 g/cm³
• LogP: 3.08640
• Storage Temp.: 2-8°C
• Water Solubility.: Miscible with ether and hot alcohol. Immiscible with water.
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 2
• Exact Mass: 178.078250319
• Heavy Atom Count: 14
• Complexity: 193

Purity/Quality:

98%,99%, ^*data from raw suppliers

Diphenylacetylene ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25-22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Aromatic Hydrocarbons
• Canonical SMILES: C1=CC=C(C=C1)C#CC2=CC=CC=C2
• Uses: Organic synthesis, purified grade, primary fluor or wavelength shifter in soluble scintillators. Diphenylacetylene is often used as a building block in organic and organometallic chemistry. It acts as dienophile and under goes Diels-Alder reaction with tetraphenylcyclopentadienone to prepare hexaphenylbenzene. It acts as a precursor in the preparation of 3-alkoxycyclopropene by reacting with benzal chloride in the presence of potassium t-butoxide.

Technology Process of Diphenylacetylene

There total 832 articles about Diphenylacetylene 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: 76.0%

2-(trimethylsilyl)phenyl trifluoromethanesulfonate (88284-48-4) + phenylacetylene (536-74-3) → 2-(phenylethynyl)-1,1'-biphenyl (10271-65-5) + diphenyl acetylene (501-65-5)

Guidance literature:

With copper(l) iodide; triphenylphosphine; cesium fluoride; In acetonitrile; for 1h; Inert atmosphere; Heating;

DOI:10.1039/b806821f

Reference yield: 64.0%

S-Phenyl benzenethiosulfonate (1212-08-4) + 2-(trimethylsilyl)phenyl trifluoromethanesulfonate (88284-48-4) + phenylacetylene (536-74-3) → diphenyl sulphone (127-63-9) + 2-(phenylethynyl)-1,1'-biphenyl (10271-65-5) + 1-phenyl-2-ethyne (143392-31-8) + diphenyl acetylene (501-65-5)

Guidance literature:

With copper(l) iodide; tetrabutyl ammonium fluoride; potassium carbonate; In acetonitrile; at 40 ℃; for 5h; Inert atmosphere; Molecular sieve;

DOI:10.1021/acs.orglett.6b02027

Reference yield: 61.0%

bromobenzene (108-86-1,52753-63-6) + para-bromotoluene (106-38-7) + Propiolic acid (471-25-0) → 1,2-bis(4-methylphenyl)acetylene (2789-88-0) + 4-(phenylethynyl)toluene (3287-02-3) + diphenyl acetylene (501-65-5)

Guidance literature:

bromobenzene; Propiolic acid; With 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl; bis(η3-allyl-μ-chloropalladium(II)); tetra-n-butylammoniumfluoride trihydrate; In 1-methyl-pyrrolidin-2-one; water; at 50 ℃; for 16h; Inert atmosphere;

para-bromotoluene; In 1-methyl-pyrrolidin-2-one; water; at 80 ℃; for 14h; Inert atmosphere;

DOI:10.1002/ejoc.201101770

upstream raw materials:

iodobenzene

phenylacetylene

copper(I) phenylacetylenide

phenylboronic acid

Downstream raw materials:

ethyl 2,3-diphenylcycloprop-2-enecarboxylate

2-Ethoxy-4,5-di-phenyl-furan

diphenyl-cycloprop-2-ene-1,1-dicarboxylic acid

1,2,3-triphenylazulene

Refernces

• 1、 Mueller et al.. "-". . p. 1129. Retrieved 1969.
• 2、 Mindiola, Daniel J.,Watson, Lori A.,Meyer, Karsten,Hillhouse, Gregory L.. "Functionalization of complexed N2O in bis(pentamethylcyclopentadienyl) systems of zirconium and titanium". . p. 2760 - 2769. Retrieved 2014.
• 3、 Mousa, Abdelrazek H.,Fleckhaus, André,Kondrashov, Mikhail,Wendt, Ola F.. "Aromatic PCN pincer palladium complexes: forming and breaking C[sbnd]C bonds". . p. 157 - 164. Retrieved 2017.
• 4、 Zupancic, Natasa,Sket, Boris. "Photoreduction of 1,1-diphenyl-2-haloethenes by metal hydrides". . p. 9071 - 9082. Retrieved 1991.
• 5、 Li, Chen-Yi,Lien, Yu-Ling,Vinayagam, Jayaramann,Datta, Amitabha,Hu, Ting-Chia,Lin, Chia-Her,Huang, Jui-Hsien. "Synthesis and characterization of copper(I) compounds incorporating pyrazole-derived ligands: A study on carbon-carbon coupling reaction". . p. 327 - 334. Retrieved 2015.
• 6、 Visser et al.. "-". . p. 178. Retrieved 1972.
• 7、 Zhao, Wen-Tao,Gao, Fang,Zhao, Dongbing. "Intermolecular σ-Bond Cross-Exchange Reaction between Cyclopropenones and (Benzo)silacyclobutanes: Straightforward Access towards Sila(benzo)cycloheptenones". . p. 6329 - 6332. Retrieved 2018.
• 8、 Hung, Rebecca R.,Grabowski, Joseph J.. "Enthalpy Measurements in Organic Solvents by Photoacoustic Calorimetry: A Solution to the Reaction Volume Problem". . p. 351 - 353. Retrieved 1992.
• 9、 Cristol,Whittemore. "-". . p. 705. Retrieved 1969.
• 10、 Wang, Deqiang,Ding, Wanjian,Hou, Guohua,Zi, Guofu,Walter, Marc D.. "Uranium versus Thorium: Synthesis and Reactivity of [η5-1,2,4-(Me3C)3C5H2]2U[η2-C2Ph2]". . p. 6767 - 6782. Retrieved 2021.