Phenyl-p-benzoquinone

Base Information

• Chemical Name: Phenyl-p-benzoquinone
• CAS No.: 363-03-1
• Molecular Formula: C12H8 O2
• Molecular Weight: 184.194
• Hs Code.: 29146990
• European Community (EC) Number: 206-654-5
• NSC Number: 2806
• UNII: KNB6553J7R
• DSSTox Substance ID: DTXSID3059892
• Nikkaji Number: J20.398J
• Wikidata: Q27889390
• ChEMBL ID: CHEMBL274117
• Mol file: 363-03-1.mol

Synonyms:phenyl-1,4-quinone;phenyl-4-quinone;phenyl-p-benzoquinone;phenylbenzoquinone;phenylbenzoquinone, ion (1-);phenylquinone;PpBQ cpd

Chemical Property of Phenyl-p-benzoquinone

Chemical Property:

• Vapor Pressure: 0.000133mmHg at 25°C
• Melting Point: 111-115 °C
• Refractive Index: 1.6086 (estimate)
• Boiling Point: 333.9°Cat760mmHg
• Flash Point: 125.2°C
• PSA: 34.14000
• Density: 1.242g/cm³
• LogP: 1.77800
• Storage Temp.: 2-8°C
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 184.052429494
• Heavy Atom Count: 14
• Complexity: 317

Purity/Quality:

99%, ^*data from raw suppliers

2-Phenyl-1,4-benzoquinone ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-42/43-20/21/22
• Safety Statements: 37/39-26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2=CC(=O)C=CC2=O
• Uses: Phenylquinone is used for small molecule-based targeting of TTD-A dimerization to control TFIIH transcriptional activity whichrepresents a potential strategy for anticancer therapy.

Technology Process of Phenyl-p-benzoquinone

There total 49 articles about Phenyl-p-benzoquinone 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%

Phenylhydroquinone (1079-21-6,140627-35-6) → 2-phenyl-1,4-benzoquinone (363-03-1)

Guidance literature:

With sodium persulfate; 1,10-Phenanthroline; phosphate buffer; copper diacetate; tetra(n-butyl)ammonium hydrogensulfate; In methanol; dichloromethane; for 0.25h;

DOI:10.1055/s-1994-25698

Reference yield: 100.0%

5-methoxy-[1,1'-biphenyl]-2-ol (13522-82-2) → 2-phenyl-1,4-benzoquinone (363-03-1)

Guidance literature:

With μ-Oxo-I,I'-bis(trifluoroacetato-O)-I,I'-diphenyldiiodine(III); In water; acetonitrile; at 0 ℃; for 2h;

DOI:10.1055/s-0031-1290579

Reference yield: 98.0%

hydroquinone (123-31-9,8027-02-9) + phenylboronic acid (98-80-6) → 2-phenyl-1,4-benzoquinone (363-03-1)

Guidance literature:

With Iron(III) nitrate nonahydrate; dipotassium peroxodisulfate; In water; at 70 ℃; for 24h; Schlenk technique;

DOI:10.1002/ejoc.201300743

upstream raw materials:

ethanol

4-hydroxy-4-phenyl-cyclohexa-2,5-dienone

sodium acetate

2-phenylaniline

Downstream raw materials:

(+/-)-5.8-dioxo-6-phenyl-(4arH.8acH)-1.4.4a.5.8.8a-hexahydro-1c.4c-methano-naphthalene

2-phenyl[1,4]naphthoquinone

2-[2]naphthyl-5-phenyl-[1,4]benzoquinone

2,5-diphenyl-p-benzoquinone

Refernces

• 1、 Pancrazzi, Francesco,Maestri, Giovanni,Maggi, Raimondo,Viscardi, Rosanna. "Oxidative Dearomatization of Phenols and Polycyclic Aromatics with Hydrogen Peroxide Triggered by Heterogeneous Sulfonic Acids". supporting information. p. 5407 - 5414. Retrieved 2021/10/25.
• 2、 Brodzka, Anna,Koszelewski, Dominik,Ostaszewski, Ryszard,Trzepizur, Damian,Wilk, Monika. "Selective Palladium-Catalyzed α,β-Homodiarylation of Vinyl Esters in Aqueous Medium". supporting information. p. 6028 - 6036. Retrieved 2021/12/10.