Pyrene, 1-(4-nitrophenyl)-

Base Information

• Chemical Name: Pyrene, 1-(4-nitrophenyl)-
• CAS No.: 95069-74-2
• Molecular Formula: C22H13NO2
• Molecular Weight: 323.351
• DSSTox Substance ID: DTXSID40477833
• Nikkaji Number: J1.632.249K
• Mol file: 95069-74-2.mol

Synonyms:Pyrene, 1-(4-nitrophenyl)-;95069-74-2;SCHEMBL9561815;DTXSID40477833

Chemical Property of Pyrene, 1-(4-nitrophenyl)-

Chemical Property:

• XLogP3: 6.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 323.094628657
• Heavy Atom Count: 25
• Complexity: 507

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C3C(=C1)C=CC4=C(C=CC(=C43)C=C2)C5=CC=C(C=C5)[N+](=O)[O-]

Technology Process of Pyrene, 1-(4-nitrophenyl)-

There total 4 articles about Pyrene, 1-(4-nitrophenyl)- 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: 78.0%

para-nitrophenyl bromide (586-78-7) + 1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrene (349666-24-6) → 1-(p-nitrophenyl)pyrene (95069-74-2)

Guidance literature:

With sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In toluene; Heating;

DOI:10.1002/1099-0690(200110)2001:20<3819::AID-EJOC3819>3.0.CO;2-W

Reference yield:

pyrene (129-00-0) + 4-nitrobenzenediazonium tetrafluoroborate (456-27-9) → 1-(p-nitrophenyl)pyrene (95069-74-2) + 2-(p-nitrophenyl)pyrene (95069-75-3)

Guidance literature:

With barium titaniate; In acetonitrile; for 1h; Overall yield = 78 percent; Milling;

DOI:10.1126/science.aay8224

Reference yield:

1-bromopyrene (1714-29-0) → 1-(p-nitrophenyl)pyrene (95069-74-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: nBuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

1.2: (iPrO)3B / tetrahydrofuran; hexane / 0.5 h / -78 - 20 °C

1.3: 85 percent / diethyl ether; hexane / 0.75 h / 40 °C

2.1: 78 percent / aq. Na₂CO₃ / Pd(PPh₃)4 / toluene / Heating

With n-butyllithium; sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; hexane; toluene; 2.1: Suzuki cross-coupling;

DOI:10.1002/1099-0690(200110)2001:20<3819::AID-EJOC3819>3.0.CO;2-W

upstream raw materials:

pyrene

4-nitro-aniline

para-nitrophenyl bromide

1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrene

Downstream raw materials:

1-(p-aminophenyl)pyrene hydrochloride

1-(p-aminophenyl)pyrene

Refernces

• 1、 Beinhoff, Matthias,Weigel, Wilfried,Jurczok, Martin,Rettig, Wolfgang,Modrakowski, Claudia,Bruedgam, Irene,Hartl, Hans,Schlueter, A. Dieter. "Synthesis and spectroscopic properties of arene-substituted pyrene derivatives as model compounds for fluorescent polarity probes". . p. 3819 - 3829. Retrieved 2007/10/03.