1,3,6,8-Tetraethynylpyrene

Base Information

• Chemical Name: 1,3,6,8-Tetraethynylpyrene
• CAS No.: 870259-02-2
• Molecular Formula: C24H10
• Molecular Weight: 298.343
• DSSTox Substance ID: DTXSID30469747
• Nikkaji Number: J2.241.292B
• Wikidata: Q82297599
• Mol file: 870259-02-2.mol

Synonyms:1,3,6,8-tetraethynylpyrene;870259-02-2;Pyrene, 1,3,6,8-tetraethynyl-;YSWG351;Pyrene,1,3,6,8-tetraethynyl;DTXSID30469747;MFCD21609448;AKOS040768755;BS-46194;CS-0110386;E74965

Chemical Property of 1,3,6,8-Tetraethynylpyrene

Chemical Property:

• Boiling Point: 526.2±50.0 °C(Predicted)
• PSA: 0.00000
• Density: 1.27±0.1 g/cm3(Predicted)
• LogP: 4.50920
• XLogP3: 6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 4
• Exact Mass: 298.078250319
• Heavy Atom Count: 24
• Complexity: 593

Purity/Quality:

97% ^*data from raw suppliers

1,3,6,8-Tetraethynylpyrene 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C#CC1=CC(=C2C=CC3=C(C=C(C4=C3C2=C1C=C4)C#C)C#C)C#C

Technology Process of 1,3,6,8-Tetraethynylpyrene

There total 4 articles about 1,3,6,8-Tetraethynylpyrene 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: 100.0%

1,3,6,8-tetrakis(2-(trimethylsilyl)ethynyl)pyrene (870258-96-1) → 1,3,6,8-tetraethynylpyrene (870259-02-2)

Guidance literature:

With potassium hydroxide; water; In methanol; dichloromethane; at 20 ℃; for 0.666667h;

DOI:10.1021/ja807530m

Reference yield:

1,3,6,8-tetrabromopyrene (128-63-2) → 1,3,6,8-tetraethynylpyrene (870259-02-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / copper(I) iodide; triphenylphosphine / bis(triphenylphosphine)palladium(II)dichloride / triethylamine; toluene / 60 - 80 °C

2: 95 percent / K₂CO₃ / methanol

With copper(l) iodide; potassium carbonate; triphenylphosphine; bis-triphenylphosphine-palladium(II) chloride; In methanol; triethylamine; toluene; 1: Hagihara-Sonogashira cross-coupling;

DOI:10.1002/chem.200500999

Reference yield:

pyrene (129-00-0) → 1,3,6,8-tetraethynylpyrene (870259-02-2)

Guidance literature:

Multi-step reaction with 3 steps

1: hydrogen bromide / nitrobenzene / 120 °C / Inert atmosphere

2: copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran; diethylamine / 39 h / 65 °C / Inert atmosphere

3: potassium carbonate / tetrahydrofuran; methanol / 1 h / 20 °C / Inert atmosphere

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; hydrogen bromide; potassium carbonate; In tetrahydrofuran; methanol; nitrobenzene; diethylamine; 2: |Sonogashira Cross-Coupling;

DOI:10.1002/chem.201202902

upstream raw materials:

1,3,6,8-tetrakis(2-(trimethylsilyl)ethynyl)pyrene

pyrene

1,3,6,8-tetrabromopyrene

Downstream raw materials:

C₄₈H₂₆O₄