2-Phenoxycyclohexa-2,5-diene-1,4-dione

Base Information

• Chemical Name: 2-Phenoxycyclohexa-2,5-diene-1,4-dione
• CAS No.: 3490-49-1
• Molecular Formula: C12H8O3
• Molecular Weight: 200.194
• NSC Number: 75681
• DSSTox Substance ID: DTXSID80291454
• Nikkaji Number: J1.801.194H
• Wikidata: Q82029416
• Mol file: 3490-49-1.mol

Synonyms:2-phenoxycyclohexa-2,5-diene-1,4-dione;3490-49-1;phenoxyquinone;2-Phenoxy-1,4-benzoquinone;NSC75681;SCHEMBL3363900;DTXSID80291454;NSC-75681;AKOS015900227

Chemical Property of 2-Phenoxycyclohexa-2,5-diene-1,4-dione

Chemical Property:

• Vapor Pressure: 0.000502mmHg at 25°C
• Refractive Index: 1.612
• Boiling Point: 313.3 °C at 760 mmHg
• Flash Point: 137.9 °C
• Density: 1.304 g/cm³
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 200.047344113
• Heavy Atom Count: 15
• Complexity: 333

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)OC2=CC(=O)C=CC2=O

Technology Process of 2-Phenoxycyclohexa-2,5-diene-1,4-dione

There total 15 articles about 2-Phenoxycyclohexa-2,5-diene-1,4-dione 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: 81.0%

2-iodocyclohexa-2,5-diene-1,4-dione (3958-83-6) + phenol (108-95-2,27073-41-2) → 2-phenoxy-1,4-benzoquinone (3490-49-1)

Guidance literature:

With potassium fluoride; In N,N-dimethyl-formamide; at 90 ℃; for 1h; Glovebox; Sealed tube;

DOI:10.1021/acs.orglett.6b01586

Reference yield: 79.0%

2-bromo-1,4-benzoquinone (3958-82-5) + phenol (108-95-2,27073-41-2) → 2-phenoxy-1,4-benzoquinone (3490-49-1)

Guidance literature:

With potassium fluoride; In N,N-dimethyl-formamide; at 90 ℃;

DOI:10.1016/0040-4039(93)85034-T

Reference yield:

sodium 2,4,6-trichlorophenolate (3784-03-0) → 2-phenoxy-1,4-benzoquinone (3490-49-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: dimethylformamide / 0.33 h

1.2: dimethylformamide

2.1: concentrated HCl / methanol; H₂O / 0.5 h

3.1: 70 percent / sodium borohydride / aq. ethanol / 0.17 h

4.1: hydrogen / 30percent Pd/C / methanol / 3.5 h

5.1: CrO₃; acetic acid / H₂O / 0.33 h / 0 - 10 °C

With chromium(VI) oxide; hydrogenchloride; sodium tetrahydroborate; hydrogen; acetic acid; 30percent Pd/C; In methanol; ethanol; water; N,N-dimethyl-formamide;

DOI:10.1021/jo020311n

upstream raw materials:

4-Amino-2-phenoxy-phenol

2-bromo-1,4-benzoquinone

phenol

2-phenoxy-1,4-dihydroquinone

Downstream raw materials:

2,5-bis(1-aziridinyl)-1,4-benzoquinone

2-phenoxy-1,4-dihydroquinone

Refernces

• 1、 Heasley, Victor L.,Anderson, James D.,Bowman, Zachery S.,Hanley Jr., John C.,Sigmund, Geoffery A.,Van Horn, David,Shellhamer, Dale F.. "Formation of dimer-type ketals in the reaction of 2,4,6-trichlorophenol and 2,4,6-trichloro-m-cresol with calcium hypochlorite in methanol: Conversion to quinones and other compounds". . p. 6827 - 6830. Retrieved 2007/10/03.