2,3-Dichloro-5,6-dicyano-1,4-benzoquinone

Base Information

• Chemical Name: 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone
• CAS No.: 84-58-2
• Molecular Formula: C8Cl2N2O2
• Molecular Weight: 227.006
• Hs Code.: 29269095
• European Community (EC) Number: 201-542-2
• NSC Number: 401087
• UNII: 1H5KD39UH7
• DSSTox Substance ID: DTXSID7052577
• Nikkaji Number: J4.898D,J510.000C
• Wikipedia: 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone
• Wikidata: Q209177
• Metabolomics Workbench ID: 155611
• ChEMBL ID: CHEMBL3759231
• Mol file: 84-58-2.mol

Synonyms:2,3-DDQ;2,3-dichloro-5,6-dicyano-1,4-benzoquinone;2,3-dichloro-5,6-dicyanobenzoquinone;dichlorodicyanobenzoquinone

Chemical Property of 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone

Chemical Property:

• Appearance/Colour: yellow to orange powder
• Vapor Pressure: 0.00103mmHg at 25°C
• Melting Point: 210-215 °C (dec.)(lit.)
• Refractive Index: 1.601
• Boiling Point: 301.8 °C at 760 mmHg
• Flash Point: 136.3 °C
• PSA: 81.72000
• Density: 1.7 g/cm³
• LogP: 1.17116
• Storage Temp.: 0-6°C
• Sensitive.: Moisture Sensitive
• Solubility.: Soluble in benzene, methanol, acetic acid and dioxane.Slightly s
• Water Solubility.: reacts
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 225.9336826
• Heavy Atom Count: 14
• Complexity: 464

Purity/Quality:

≥99% ^*data from raw suppliers

2,3-Dichloro-5,6-dicyanobenzoquinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25-29-41-37/38-20/21-23/24/25
• Safety Statements: 22-24/25-37-45-36/37-26-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Other Aromatics (Nitrogen)
• Canonical SMILES: C(#N)C1=C(C(=O)C(=C(C1=O)Cl)Cl)C#N
• Description: 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) has a variety of applications. DDQ is a deprotection agent for ketals, acetals, and thioacetals. It is a useful electron transfer reagent for synthesis of quinolones and an oxidizing agent used to synthesize steroids. Additionally, DDQ is used with Ph3P to synthesize 1,2-benzisoxazoles.
• Uses: An oxidizing agent, especially in steroid synthesis.2,3-Dichloro-5,6-dicyano-1,4-benzoquinone is used as a reagent for oxidative couplings and cyclization reactions and dehydrogenation of alcohols, phenols and steroid ketones. It is also used in the synthesis of 1,2-benzisoxazoles. It is a useful electron-transfer reagent for synthesis of quinolines from imines and alkynes or alkenes.

Technology Process of 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone

There total 44 articles about 2,3-Dichloro-5,6-dicyano-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: 96.0%

C10H10N4O2 → 2,3-dicyano-5,6-dichloro-p-benzoquinone (84-58-2)

Guidance literature:

C₁₀H₁₀N₄O₂; With sodium chloride; at 38 ℃; for 2h;

With ethyl 3-chloropropanoate; tetracarbonyl nickel; at 45 ℃; for 3h; Temperature;

Reference yield:

2C6H8N2*C8Cl2N2O2 → 2-Amino-6-methylpyridine (1824-81-3) + 2,3-dicyano-5,6-dichloro-p-benzoquinone (84-58-2)

Guidance literature:

at 207 - 260 ℃;

DOI:10.1016/j.molstruc.2019.127021

Reference yield:

4,5-dichloro-3,6-dioxo-cyclohexa-1,4-diene-1,2-dicarbonitrile; compound with acenaphthylene → 2,3-dicyano-5,6-dichloro-p-benzoquinone (84-58-2) + acenaphthylene (208-96-8,25036-01-5)

Guidance literature:

In 1,2-dichloro-ethane; Equilibrium constant;

DOI:10.1039/b200098a

upstream raw materials:

2,3-dichloro-5,6-dicyanohydroquinone

pyrene - 2,3-dichloro-5,6-dicyano-p-benzoquinone complex

[2,2']Bi[[1,3]dithiolylidene]

C₁₄H₁₃NO*C₈Cl₂N₂O₂

Downstream raw materials:

1-benzoyl-1,2,3,4-tetrahydro-naphtho[2,3-g]quinoline

dimethyl-1,2 naphtalene

6-methylbenzo[a]anthracene

3-methylbenz[a]anthracene

Refernces

• 1、 Walker,Waugh. "-". . p. 3240. Retrieved 1965.
• 2、 -. "Synthetic method for gestrinone drug intermediate dichlorodicyanobenzoquinone". Paragraph 0013; 0016-0027. . Retrieved 2018/07/30.
• 3、 Haga, Naoki,Takayanagi, Hiroaki,Tokumaru, Katsumi. "Photoinduced electron transfer between acenaphthylene and 1,4-benzoquinones. Formation of dimers of acenaphthylene and 1 : 1-adducts and effect of excitation mode on reactivity of the charge-transfer complexes". . p. 734 - 745. Retrieved 2007/10/03.