3,3'-(1,4-Phenylene)bis(2,4,5-triphenylcyclopentadienone)

Base Information

• Chemical Name: 3,3'-(1,4-Phenylene)bis(2,4,5-triphenylcyclopentadienone)
• CAS No.: 3432-73-3
• Molecular Formula: C52H34O2
• Molecular Weight: 690.841
• DSSTox Substance ID: DTXSID00385349
• Nikkaji Number: J1.318.266C
• Wikidata: Q82178075
• Mol file: 3432-73-3.mol

Synonyms:3,3'-(1,4-Phenylene)bis(2,4,5-triphenylcyclopentadienone);3432-73-3;SCHEMBL4250744;DTXSID00385349;CDSWVVKOGGSZOB-UHFFFAOYSA-N;STK533606;AKOS005465351;1,4-bis(1-oxo-2,4,5-triphenylcyclopentadien-3-yl)benzene;3,3'-(p-Phenylene)bis(2,4,5-triphenyl-2,4-cyclopentadiene-1-one);3,3'-benzene-1,4-diylbis(2,4,5-triphenylcyclopenta-2,4-dien-1-one);4,4'-(1,4-PHENYLENE)BIS(2,3,5-TRIPHENYLCYCLOPENTA-2,4-DIENONE)

Chemical Property of 3,3'-(1,4-Phenylene)bis(2,4,5-triphenylcyclopentadienone)

Chemical Property:

• Melting Point: 302-304 °C
• PSA: 34.14000
• Density: 1.252g/cm3
• LogP: 11.89560
• XLogP3: 10.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 8
• Exact Mass: 690.255880323
• Heavy Atom Count: 54
• Complexity: 1370

Purity/Quality:

98%+ ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2=C(C(=O)C(=C2C3=CC=C(C=C3)C4=C(C(=O)C(=C4C5=CC=CC=C5)C6=CC=CC=C6)C7=CC=CC=C7)C8=CC=CC=C8)C9=CC=CC=C9

Technology Process of 3,3'-(1,4-Phenylene)bis(2,4,5-triphenylcyclopentadienone)

There total 5 articles about 3,3'-(1,4-Phenylene)bis(2,4,5-triphenylcyclopentadienone) 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: 88.0%

1,4-bis(phenylglyoxalyl)benzene (3363-97-1) + 1,3-Diphenylpropanone (102-04-5) → 3,3'-(1,4-phenylene)bis(2,4,5-triphenylcyclopenta-2,4-dien-1-one) (3432-73-3)

Guidance literature:

With potassium hydroxide; In ethanol; for 1.75h; Reflux;

DOI:10.1021/jacs.5b07865

Reference yield:

1,4-bis(2-phenylethynyl)benzene (1849-27-0) → 3,3'-(1,4-phenylene)bis(2,4,5-triphenylcyclopenta-2,4-dien-1-one) (3432-73-3)

Guidance literature:

Multi-step reaction with 2 steps

1: periodic acid; acetic acid / 20 h / 55 °C

2: potassium hydroxide / ethanol; toluene; methanol / 1 h / 130 °C

With acetic acid; periodic acid; potassium hydroxide; In methanol; ethanol; toluene;

DOI:10.1016/j.electacta.2013.11.190

Reference yield:

para-diiodobenzene (624-38-4,1032416-46-8) → 3,3'-(1,4-phenylene)bis(2,4,5-triphenylcyclopenta-2,4-dien-1-one) (3432-73-3)

Guidance literature:

Multi-step reaction with 3 steps

1: copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran / 20 h / 20 °C / Inert atmosphere

2: periodic acid; acetic acid / 20 h / 55 °C

3: potassium hydroxide / ethanol; toluene; methanol / 1 h / 130 °C

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; acetic acid; periodic acid; triethylamine; potassium hydroxide; In tetrahydrofuran; methanol; ethanol; toluene; 1: |Sonogashira Cross-Coupling;

DOI:10.1016/j.electacta.2013.11.190

upstream raw materials:

1,4-bis(phenylglyoxalyl)benzene

1,3-Diphenylpropanone

1,4-bis (phenylacetyl)benzene

benzylmagnesium chloride

Downstream raw materials:

C₆₄H₄₆O₂

2',2''',3',3''',5',5''',6',6'''-octaphenyl-p-quinquephenyl

1,4-Bis(1,3,4-triphenyl-5-hydroxy-1,3-cyclopentadien-2-yl)benzol

1,4-Bis-(2,3,4,5,6,7-hexaphenylcycloheptatri-1,3,6-enyl)-benzol