2-Phenyl-1,4-naphthoquinone

Base Information

• Chemical Name: 2-Phenyl-1,4-naphthoquinone
• CAS No.: 2348-77-8
• Molecular Formula: C16H10 O2
• Molecular Weight: 234.254
• Hs Code.: 2914690090
• NSC Number: 167124
• DSSTox Substance ID: DTXSID60304738
• Nikkaji Number: J465.581H
• Wikidata: Q82050901
• ChEMBL ID: CHEMBL1762552
• Mol file: 2348-77-8.mol

Synonyms:2-Phenyl-1,4-naphthoquinone;2-phenylnaphthalene-1,4-dione;2348-77-8;Anti-infective agent 1;CHEMBL1762552;1,4-Naphthoquinone, 2-phenyl-;1,4-Naphthalenedione, 2-phenyl-;NSC167124;2-Phenylnaphthoquinone;2-Phenylnaphthoquinone #;SCHEMBL5485068;2 - Phenyl-1,4-naphthoquinone;DTXSID60304738;CIDYIYSNDAJNGX-UHFFFAOYSA-N;HMS1580M15;BDBM50340585;AKOS040758949;NSC-167124;HY-146487;CS-0499123;AE-641/00823016

Chemical Property of 2-Phenyl-1,4-naphthoquinone

Chemical Property:

• Vapor Pressure: 4.51E-07mmHg at 25°C
• Boiling Point: 414.3°Cat760mmHg
• Flash Point: 155°C
• PSA: 34.14000
• Density: 1.268g/cm³
• LogP: 3.14920
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 234.068079557
• Heavy Atom Count: 18
• Complexity: 388

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2=CC(=O)C3=CC=CC=C3C2=O

Technology Process of 2-Phenyl-1,4-naphthoquinone

There total 73 articles about 2-Phenyl-1,4-naphthoquinone 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: 94.0%

2-bromo-1,4-naphthoquinone (2065-37-4) + phenylboronic acid (98-80-6) → 2-phenyl[1,4]naphthoquinone (2348-77-8)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; caesium carbonate; In tetrahydrofuran; water; at 65 ℃; for 1.5h; Reagent/catalyst; Temperature; Catalytic behavior; Inert atmosphere;

DOI:10.1016/j.ejmech.2020.112837

Reference yield: 94.0%

[1,4]naphthoquinone (130-15-4) + benzene (71-43-2,26181-88-4,54682-86-9,13967-78-7,174973-66-1) → 2-phenyl[1,4]naphthoquinone (2348-77-8)

Guidance literature:

With ammonium peroxydisulfate; palladium diacetate; trifluoroacetic acid; at 20 ℃; for 24h; Schlenk technique;

DOI:10.1039/c4cc05827e

Reference yield: 94.0%

2-bromo-1,4-naphthoquinone (2065-37-4) + 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole (24388-23-6) → 2-phenyl[1,4]naphthoquinone (2348-77-8)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; caesium carbonate; In tetrahydrofuran; water; at 65 ℃; for 2h; Reagent/catalyst; Inert atmosphere;

DOI:10.1016/j.ejmech.2020.112837

upstream raw materials:

ethanol

buta-1,3-diene

2-phenyl-1,4-benzoquinone

benzenediazonium

Downstream raw materials:

1-(4-Chloro-phenyl)-7a-phenyl-1a,7a-dihydro-1H-1-aza-cyclopropa[b]naphthalene-2,7-dione

2-{[(Z)-4-Chloro-phenylimino]-methyl}-2-phenyl-indan-1,3-dione

2-(4-Chloro-phenylamino)-3-phenyl-[1,4]naphthoquinone

2-phenyl-naphthalene-1,4-diol

Refernces

• 1、 Harrity,Kerr,Middlemiss. "Promotion of the chromium carbene dotz annulation reaction under dry state adsorption conditions". . p. 2995 - 2998. Retrieved 1993.
• 2、 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.
• 3、 Kalt, Marc-Manuel,Schuehly, Wolfgang,Saf, Robert,Ochensberger, Sandra,Solnier, Julia,Bucar, Franz,Kaiser, Marcel,Presser, Armin. "Palladium-catalysed synthesis of arylnaphthoquinones as antiprotozoal and antimycobacterial agents". supporting information. . Retrieved 2020/10/06.