2,3-Dimethyl-p-benzoquinone

Base Information

• Chemical Name: 2,3-Dimethyl-p-benzoquinone
• CAS No.: 526-86-3
• Molecular Formula: C8H8O2
• Molecular Weight: 136.15
• Hs Code.: 2914690090
• NSC Number: 402192
• UNII: 6DVX468HU4
• DSSTox Substance ID: DTXSID10200579
• Nikkaji Number: J6.664H
• Wikidata: Q72469426
• ChEMBL ID: CHEMBL357033
• Mol file: 526-86-3.mol

Synonyms:2,3-dimethyl-2,5-cyclohexadiene-1,4 dione;2,3-dimethyl-4-benzoquinone;2,3-dimethyl-p-benzoquinone

Chemical Property of 2,3-Dimethyl-p-benzoquinone

Chemical Property:

• Vapor Pressure: 0.326mmHg at 25°C
• Melting Point: 55-57℃
• Refractive Index: 1.51
• Boiling Point: 200.3 °C at 760 mmHg
• Flash Point: 70.9 °C
• PSA: 34.14000
• Density: 1.115 g/cm³
• LogP: 1.03080
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform, DMSO (Slightly), Methanol (Slightly)
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 136.052429494
• Heavy Atom Count: 10
• Complexity: 230

Purity/Quality:

98% ^*data from raw suppliers

2,3-Dimethylbenzoquinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Aromatic Ketones
• Canonical SMILES: CC1=C(C(=O)C=CC1=O)C
• Uses: 2,3-Dimethylbenzoquinone is a reagent in the preparation of hydroxycinnolines which has antifungal activity.

Technology Process of 2,3-Dimethyl-p-benzoquinone

There total 35 articles about 2,3-Dimethyl-p-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: 100.0%

2,3-dimethyl-1,4-dihydroxybenzene (608-43-5) → 2,3-dimethyl-1,4-benzoquinone (526-86-3)

Guidance literature:

With benzyltrimethylammonium tribromide; sodium acetate; In dichloromethane; water; for 2h; Ambient temperature;

DOI:10.1246/bcsj.64.336

Reference yield: 96.3%

2,3-dibromo-5,6-dimethylcyclohexa-2,5-diene-1,4-dione (38969-08-3) → 2,3-dimethyl-1,4-benzoquinone (526-86-3)

Guidance literature:

With iron; acetic acid; at 20 ℃; for 6h; Reflux;

Reference yield: 93.0%

3,6-dimethoxy-o-xylene (39021-83-5) → 2,3-dimethyl-1,4-benzoquinone (526-86-3)

Guidance literature:

With cerium(IV) ammonium nitrate; silica gel; In dichloromethane; for 0.25h;

DOI:10.1080/00397910600616859

upstream raw materials:

2,3-Dimethylphenol

lead(IV) tetraacetate

acetic acid

2,3-Dimethylaniline

Downstream raw materials:

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

5-[ethyl-(2-chloro-ethyl)-amino]-2,3-dimethyl-[1,4]benzoquinone

2,3-dibromo-5,6-dimethylcyclohexa-2,5-diene-1,4-dione

2,3-dimethyl-[1,4]benzoquinone monooxime

Refernces

• 1、 Ficht, Simon,Mülbaier, Marcel,Giannis, Athanassios. "Development of new and efficient polymer-supported hypervalent iodine reagents". . p. 4863 - 4866. Retrieved 2001.
• 2、 Kotha, Sambasivarao,Banerjee, Shaibal,Shaikh, Mobin. "Correlation between carbon-carbon bond length and the ease of retro Diels-Alder reaction". . p. 1369 - 1371. Retrieved 2014.
• 3、 Feldman, Ken S.,Hester II, D. Keith,Golbeck, John H.. "A relationship between amide hydrogen bond strength and quinone reduction potential: Implications for photosystem I and bacterial reaction center quinone function". . p. 4891 - 4894. Retrieved 2007.
• 4、 Rodriguez, Jose-Gonzalo,Pablo, Alfonso De,Smith-Verdier, Pilar. "Structural Study of the Methylnaphthazarins. X-Ray Structure of the Tetramethylnaphthazarin, a Charge Transfer Complex". . p. 3957 - 3962. Retrieved 1986.
• 5、 Boelke, Andreas,Lork, Enno,Nachtsheim, Boris J.,Sadat, Soleicha. "Pseudocyclic bis-N-heterocycle-stabilized iodanes - synthesis, characterization and applications". supporting information. p. 7434 - 7437. Retrieved 2021/08/03.
• 6、 Llopis, Natalia,Baeza, Alejandro. "Oxidation of Electron-Rich Arenes Using HFIP-UHP System". . p. 6159 - 6164. Retrieved 2020/05/20.