2,5-Diphenyl-1,4-benzoquinone

Base Information

• Chemical Name: 2,5-Diphenyl-1,4-benzoquinone
• CAS No.: 844-51-9
• Molecular Formula: C18H12 O2
• Molecular Weight: 260.292
• Hs Code.: 2914399090
• European Community (EC) Number: 212-680-8
• NSC Number: 8725
• UNII: 19F7OO1LXR
• DSSTox Substance ID: DTXSID9061207
• Nikkaji Number: J39.605B
• Wikidata: Q72469361
• ChEMBL ID: CHEMBL1762559
• Mol file: 844-51-9.mol

Synonyms:2,5-diphenyl-4-benzoquinone;diphenyl-p-benzoquinone

Chemical Property of 2,5-Diphenyl-1,4-benzoquinone

Chemical Property:

• Appearance/Colour: bright yellow powder
• Vapor Pressure: 1.43E-08mmHg at 25°C
• Melting Point: 215-217°C
• Boiling Point: 457.9 °C at 760 mmHg
• Flash Point: 170.5 °C
• PSA: 34.14000
• Density: 1.237 g/cm³
• LogP: 3.30540
• Solubility.: Soluble in hot Toluene (almost transparency).
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 260.083729621
• Heavy Atom Count: 20
• Complexity: 414

Purity/Quality:

99% ^*data from raw suppliers

2,5-Diphenyl-1,4-benzoquinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2=CC(=O)C(=CC2=O)C3=CC=CC=C3
• Uses: 2,5-Diphenyl-p-benzoquinone is used as pharmaceutical intermediate.

Technology Process of 2,5-Diphenyl-1,4-benzoquinone

There total 29 articles about 2,5-Diphenyl-1,4-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: 80.0%

2’,5’-dimethoxy-1,1’:4’,1”-terphenyl (100151-17-5) → 2,5-diphenyl-p-benzoquinone (844-51-9)

Guidance literature:

With ammonium cerium(IV) nitrate; In water; acetonitrile; for 0.0833333h;

DOI:10.1021/jo9721812

Reference yield: 44.0%

p-benzoquinone (106-51-4) + phenylboronic acid (98-80-6) → 2,6-diphenyl-[1,4]benzoquinone (2887-97-0) + 2,5-diphenyl-p-benzoquinone (844-51-9)

Guidance literature:

With 2,6-dichloro-1,4-benzoquinone; palladium trifluoroacetate; In acetone; at 20 ℃; for 48h; regioselective reaction;

DOI:10.1002/anie.201408054

Reference yield: 28.0%

hydroquinone (123-31-9,8027-02-9) + benzene (71-43-2,26181-88-4,54682-86-9,13967-78-7,174973-66-1) → 2,6-diphenyl-[1,4]benzoquinone (2887-97-0) + 2,5-diphenyl-p-benzoquinone (844-51-9) + 2-phenyl-1,4-benzoquinone (363-03-1)

Guidance literature:

With palladium(II) acetylacetonate; dimethyl sulfoxide; silver carbonate; Trimethylacetic acid; at 140 ℃; for 24h; Sealed tube;

DOI:10.1039/c3cc41067f

upstream raw materials:

2,2-dibromo-1-phenylpropan-1-one

N-nitrosoacetanilide

2-phenyl-1,4-benzoquinone

benzenediazonium

Downstream raw materials:

3,6-diphenyl-2,5-dimethoxy-1,4-benzoquinone

2,5-diphenyl-1,4-dihydroxybenzene

{Pt(C₆H₂O₂(C₆H₅)2)(C₂H₄)(P(C₆H₁₁)3)}

{Pt(C₆H₂(C₆H₅)2O₂)(C₈H₁₂)}

Refernces

• 1、 Zhang, Shuai,Song, Feijie,Zhao, Dongbing,You, Jingsong. "Tandem oxidation-oxidative C-H/C-H cross-coupling: Synthesis of arylquinones from hydroquinones". supporting information. p. 4558 - 4560. Retrieved 2013/06/04.
• 2、 Palmgren, Andreas,Thorarensen, Atli,Baeckvall, Jan-E.. "Efficient Synthesis of Symmetrical 2,5-Disubstituted Benzoquinones via Palladium-Catalyzed Double Negishi Coupling". . p. 3764 - 3768. Retrieved 2007/10/03.