Benzofuran, 2-(1-phenylethenyl)-

Base Information

• Chemical Name: Benzofuran, 2-(1-phenylethenyl)-
• CAS No.: 56426-70-1
• Molecular Formula: C16H12O
• Molecular Weight: 220.271
• DSSTox Substance ID: DTXSID30481207
• Wikidata: Q82316474

Synonyms:2-(1-Phenylvinyl)benzofuran;56426-70-1;Benzofuran, 2-(1-phenylethenyl)-;DTXSID30481207

Chemical Property of Benzofuran, 2-(1-phenylethenyl)-

Chemical Property:

• XLogP3: 5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 220.088815002
• Heavy Atom Count: 17
• Complexity: 277

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C=C(C1=CC=CC=C1)C2=CC3=CC=CC=C3O2

Technology Process of Benzofuran, 2-(1-phenylethenyl)-

There total 3 articles about Benzofuran, 2-(1-phenylethenyl)- 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: 87.0%

2-benzoylbenzofuran (6272-40-8) + Methyltriphenylphosphonium bromide (1779-49-3) → 2-(1-phenylvinyl)benzofuran (56426-70-1)

Guidance literature:

Methyltriphenylphosphonium bromide; With n-butyllithium; In tetrahydrofuran; hexane; at 0 - 20 ℃; for 1h; Inert atmosphere;

2-benzoylbenzofuran; In tetrahydrofuran; hexane; at 0 - 20 ℃; for 1h; Inert atmosphere;

DOI:10.1021/acs.joc.8b00360

Reference yield: 76.0%

1-phenyl-1-iodoethylene (51246-20-9) + o-((trimethylsilyl)ethynyl)phenol (81787-62-4) → 2-(1-phenylvinyl)benzofuran (56426-70-1)

Guidance literature:

1-phenyl-1-iodoethylene; With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1,8-diazabicyclo[5.4.0]undec-7-ene; In water; N,N-dimethyl-formamide; at 20 ℃; for 0.0333333h;

o-((trimethylsilyl)ethynyl)phenol; In water; N,N-dimethyl-formamide; at 20 ℃; for 12h;

DOI:10.1002/ejoc.201100540

Reference yield:

2-(trimethylsilyl)phenyl trifluoromethanesulfonate (88284-48-4) → 2-(1-phenylvinyl)benzofuran (56426-70-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: cesium fluoride / 0.17 h / 20 °C / Inert atmosphere

2.1: 12 h / 20 °C / Inert atmosphere

3.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 - 20 °C / Inert atmosphere

3.2: 1 h / 0 - 20 °C / Inert atmosphere

With n-butyllithium; cesium fluoride; In tetrahydrofuran; hexane; 3.1: |Wittig Olefination;

DOI:10.1021/acs.joc.8b00360

upstream raw materials:

1-phenyl-1-iodoethylene

o-((trimethylsilyl)ethynyl)phenol

2-benzoylbenzofuran

Methyltriphenylphosphonium bromide

Downstream raw materials:

6-phenylanthra<2,1-b>benzofuran-8,13-dione

5c-hydroperoxy-2,5t-diphenyl-(3ar,10cc)-3a,4,5,10c-tetrahydro-benzo[4,5]furo[3,2-e]isoindole-1,3-dione

5t-hydroperoxy-2,5c-diphenyl-(3ar,10cc)-3a,4,5,10c-tetrahydro-benzo[4,5]furo[3,2-e]isoindole-1,3-dione

5-(2-benzofuryl)benzanthracene-7,12-dione

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