2,5-Dichloro-1,4-benzoquinone

Base Information

• Chemical Name: 2,5-Dichloro-1,4-benzoquinone
• CAS No.: 615-93-0
• Deprecated CAS: 78844-56-1
• Molecular Formula: C6H2Cl2O2
• Molecular Weight: 176.987
• Hs Code.: 2914700090
• European Community (EC) Number: 210-453-8
• NSC Number: 6251
• DSSTox Substance ID: DTXSID9060657
• Nikkaji Number: J65.481G
• Wikidata: Q69759030
• ChEMBL ID: CHEMBL3311439
• Mol file: 615-93-0.mol

Synonyms:2,5-DCBQ;2,5-dichlorobenzoquinone

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

Chemical Property:

• Appearance/Colour: yellow powder
• Vapor Pressure: 0.0358mmHg at 25°C
• Melting Point: 160-163 °C
• Refractive Index: 1.568
• Boiling Point: 241.5 °C at 760 mmHg
• Flash Point: 98.5 °C
• PSA: 34.14000
• Density: 1.56 g/cm³
• LogP: 1.38360
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: soluble in Methanol
• Water Solubility.: Insoluble in water.
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 175.9431847
• Heavy Atom Count: 10
• Complexity: 235

Purity/Quality:

98% ^*data from raw suppliers

2,5-Dichlorocyclohexa-2,5-diene-1,4-dione ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=C(C(=O)C=C(C1=O)Cl)Cl
• Uses: 2,5-Dichloro-1,4-benzoquinone may be used in the following processes:As a starting material in the synthesis of asterriquinone D.As a model to study the utility of a novel photoreactor with LED (light-emitting diode) light source and a fibre-optic CCD (charge-coupled device) spectrophotometer.2,5-dichloro-3,6-bi(3-indolyl)-1,4-hydroquinone synthesis by palladium catalyzed reaction with indole.

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

There total 47 articles about 2,5-Dichloro-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: 85.0%

2,5-dichloro-1,4-phenylenediamine (20103-09-7) → 2,5-Dichloro-1,4-benzoquinone (615-93-0)

Guidance literature:

With perchloric acid; at 25 ℃; for 0.516667h; Electrochemical reaction;

Reference yield: 76.0%

2,5-dichloro-1,4-hydroquinone (824-69-1) → 2,5-Dichloro-1,4-benzoquinone (615-93-0)

Guidance literature:

With silver(l) oxide; In diethyl ether; for 0.5h;

DOI:10.1021/ja00288a035

Reference yield: 70.0%

p-benzoquinone (106-51-4) → 2,5-Dichloro-1,4-benzoquinone (615-93-0)

Guidance literature:

With chlorine; mercury(II) oxide; In tetrachloromethane; for 0.5h;

DOI:10.1080/00397919408011701

upstream raw materials:

2,5 dichloroaniline

ethanol

2,3,5,6-tetrachlorocyclohexa-2,5-diene-1,4-dione

1,4-dichloro-2,5-dimethoxybenzene

Downstream raw materials:

2,5-Dichlor-3,6-dimorpholin-p-benzochinon

2,5-dichloro-3,6-diphenyl-[1,4]benzoquinone

2,5-Bis-(4-acetoxy-phenyl)-3,6-dichlor-benzo-1,4-chinon

2,3,5,6-tetrachlorobenzene-1,4-diol

Refernces

Synthesis of 3-Indolyl-2,5-dihydroxybenzoquinones

10.1021/ol006852l

The research describes a novel and efficient method for synthesizing 3-indolyl-2,5-dihydroxybenzoquinones, a substructure found in biologically significant natural products like the asterriquinones, which are known for their antitumor properties and other biological activities. The purpose of the study is to develop a synthetic route that could be used in the total syntheses of asterriquinones or to prepare reagents for probing the biological activity of indolylquinones. The process involves the acid-catalyzed condensation of indoles with 2,5-dichlorobenzoquinone, followed by DDQ oxidation, resulting in dichloroquinones that are then hydrolyzed to produce the 3-indolyldihydroxybenzoquinones.