2,6-Dichloro-1,4-benzoquinone

Base Information

• Chemical Name: 2,6-Dichloro-1,4-benzoquinone
• CAS No.: 697-91-6
• Molecular Formula: C6H2 Cl2 O2
• Molecular Weight: 176.987
• Hs Code.: 2914700090
• European Community (EC) Number: 211-810-0
• NSC Number: 6211
• DSSTox Substance ID: DTXSID7061019
• Nikkaji Number: J24.263B
• Wikidata: Q63409002
• Mol file: 697-91-6.mol

Synonyms:2,6-dichlorobenzoquinone;DCBQ

Chemical Property of 2,6-Dichloro-1,4-benzoquinone

Chemical Property:

• Appearance/Colour: yellow crystalline powder
• Vapor Pressure: 0.0358mmHg at 25°C
• Melting Point: 122-124 °C(lit.)
• Refractive Index: 1.568
• Boiling Point: 241.5°C at 760 mmHg
• Flash Point: 98.5°C
• PSA: 34.14000
• Density: 1.56g/cm³
• LogP: 1.38360
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: Insoluble in water. Solubility in methanol (almost transparency).
• 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: 239

Purity/Quality:

97% ^*data from raw suppliers

2,6-Dichloro-1,4-benzoquinone ^*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:

• Chemical Classes: Other Classes -> Aromatic Ketones, Halogenated
• Canonical SMILES: C1=C(C(=O)C(=CC1=O)Cl)Cl
• Uses: 2,6-Dichloro-1,4-benzoquinone is the suitable reagent used to in a study to evaluate the diffusion coefficients (D) for a family of quinones, nitroaromatics, ferrocenes and aromatic hydrocarbon compounds, in acetonitrile by single potential step chronoamperometry.1 It may be used in the preparation of 2,3,5-Trichloro-1,4-dihydroquinone, 2,3,5-trichloro-1,4-benzoquinone and 2,6-Dichloro-1,4-dihydroquinone.

Technology Process of 2,6-Dichloro-1,4-benzoquinone

There total 66 articles about 2,6-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: 99.4%

2,4,6-Trichlorophenol (88-06-2,67471-29-8) → 2,6-dichloro-1,4-benzoquinone (697-91-6)

Guidance literature:

With oxygen; nitric acid; In methanol; at 20 ℃; for 2h; Sealed tube;

Reference yield: 94.0%

2,6-dichloro-1,4-benzenediol (20103-10-0) → 2,6-dichloro-1,4-benzoquinone (697-91-6)

Guidance literature:

With (phthalocyaninato)iron(II); zeolite; air; In 1,4-dioxane; water; at 20 ℃; for 6h;

DOI:10.1081/SCC-120004139

Reference yield: 93.8%

2,6-Dichlorophenol (87-65-0) → 2,6-dichloro-1,4-benzoquinone (697-91-6)

Guidance literature:

With tert.-butylhydroperoxide; 3K⁽¹⁺⁾*BO₄₀W₁₂^(5-)*14H₂O*4C₃H₃N₄O₂^(1-)*2C₃H₄N₄O₂*3Cu⁽²⁺⁾; at 60 ℃; for 0.75h; Reagent/catalyst;

DOI:10.1039/d1gc03061b

upstream raw materials:

2,4,6-Trichlorophenol

benzene

2,6-dichloro-4-nitrophenol

[bis(acetoxy)iodo]benzene

Downstream raw materials:

2,5-bis-aziridin-1-yl-3-chloro-[1,4]benzoquinone

1,1-Diphenylethylene

2,6-dichloro-[1,4]benzoquinone; compound of 2.6-dichloro-quinone with 2.6-dichloro-hydroquinone

6,8-dichloro-3,3-diphenyl-1-oxa-spiro[3.5]nona-5,8-diene-2,7-dione

Refernces

Cross-metathesis between α-methylene-γ-butyrolactone and olefins: A dramatic additive effect

10.1021/ol0703940

The research focuses on the cross-metathesis reaction between r-methylene-γ-butyrolactone and terminal olefins, aiming to develop an efficient and highly stereoselective method for synthesizing r-alkylidene-γ-butyrolactones, which are valuable building blocks in organic synthesis. The experiments involved using various ruthenium-based catalysts, with [Ru]-II being the most effective, and a range of additives to enhance the reaction efficiency and minimize the formation of undesired isomerized byproducts. The reactions were conducted in refluxing CH2Cl2, with the products and reaction progress analyzed using 1H NMR spectroscopy. Key additives identified were chlorocatecholborane and 2,6-dichloro-1,4-benzoquinone, which significantly improved the reaction's yield and selectivity. The study also explored the reaction with a variety of olefinic partners, achieving moderate to excellent yields with high E-stereoselectivity.