1,5-Diphenyl-1,3-pentadiyne

Base Information

• Chemical Name: 1,5-Diphenyl-1,3-pentadiyne
• CAS No.: 6088-99-9
• Molecular Formula: C17H12
• Molecular Weight: 216.282
• NSC Number: 89015
• DSSTox Substance ID: DTXSID00976357
• Nikkaji Number: J2.159.735J
• Wikidata: Q82961223
• Mol file: 6088-99-9.mol

Synonyms:6088-99-9;NSC89015;DTXSID00976357;NSC-89015;1,1'-(Penta-1,3-diyne-1,5-diyl)dibenzene

Chemical Property of 1,5-Diphenyl-1,3-pentadiyne

Chemical Property:

• Boiling Point: 371.8°Cat760mmHg
• Flash Point: 171.8°C
• Density: 1.08g/cm³
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 3
• Exact Mass: 216.093900383
• Heavy Atom Count: 17
• Complexity: 339

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CC#CC#CC2=CC=CC=C2

Technology Process of 1,5-Diphenyl-1,3-pentadiyne

There total 4 articles about 1,5-Diphenyl-1,3-pentadiyne 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: 98.0%

propargyl benzene (10147-11-2) + 1-(phenylethynyl)-3,3-bis(trifluoromethyl)-1,3-dihydro-1λ3-benzo[d][1,2]iodaoxole → penta-1,3-diyne-1,5-diyldibenzene (6088-99-9)

Guidance literature:

With 1,10-Phenanthroline; triazole; silver(I) 4-methylbenzenesulfonate; In acetonitrile; at 20 ℃; for 2h; Schlenk technique; Inert atmosphere;

DOI:10.1002/anie.201702833

Reference yield: 93.0%

2-chloro-4-phenyl-1-buten-3-yne (13524-10-2) + benzyl bromide (100-39-0) → penta-1,3-diyne-1,5-diyldibenzene (6088-99-9)

Guidance literature:

2-chloro-4-phenyl-1-buten-3-yne; With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at -78 - -30 ℃; for 1h;

With zinc dibromide; In tetrahydrofuran; hexane; at -30 - 0 ℃; for 0.5h;

benzyl bromide; dichloro[bis(2-(diphenylphosphino)phenyl)ether]palladium(ll); In tetrahydrofuran; hexane; at 23 ℃; for 3h;

DOI:10.1016/j.tetlet.2005.02.137

Reference yield:

buta-1,3-diynylbenzene (5701-81-5) + benzyl tosylate (1024-41-5) → penta-1,3-diyne-1,5-diyldibenzene (6088-99-9)

Guidance literature:

Multistep reaction; (i) EtMgBr, THF, (ii) /BRN= 2217278/;

DOI:10.1016/0040-4020(66)80058-3

upstream raw materials:

buta-1,3-diynylbenzene

benzyl tosylate

2-chloro-4-phenyl-1-buten-3-yne

benzyl bromide

Refernces

• 1、 Qian, Mingxing,Negishi, Ei-Ichi. "Palladium-catalyzed cross-coupling reaction of alkynylzincs with benzylic electrophiles". . p. 2927 - 2930. Retrieved 2007/10/03.