553-97-9

Basic information

• Product Name: p-Toluquinone
• Synonyms: methylquinone;para-toluquinone;p-Benzoquinone,2-methyl-;Tolylquinone;2-methylnaphthalene-1,4-dione;Methyl-1,4-benzoquinone,98%;Methyl-p-benzoquinone, 99+%;2-METHYL-PARA-BENZOQUINONE
• CAS NO: 553-97-9
• Molecular Formula: C₇H₆O₂
• Molecular Weight: 122.12
• EINECS: 209-056-2
• Product Categories: Intermediates of Dyes and Pigments;Benzoquinones
• Mol File: 553-97-9.mol
• Article Data: 168

Chemical Properties

• Melting Point: 66-67 °C(lit.)
• Boiling Point: 187.52°C (rough estimate)
• Flash Point: 64.9 °C
• Appearance: Yellowish green/Crystalline
• Density: 1.0800
• Vapor Pressure: 0.656mmHg at 25°C
• Refractive Index: 1.5286 (estimate)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Water Solubility: insoluble
• BRN: 471387
• CAS DataBase Reference: p-Toluquinone(CAS DataBase Reference)
• NIST Chemistry Reference: p-Toluquinone(553-97-9)
• EPA Substance Registry System: p-Toluquinone(553-97-9)

Safety Data

• Hazard Codes: Xn,T
• Statements: 22-36/37/38-25
• Safety Statements: 26-45-37/39-28A
• WGK Germany: 3
• RTECS: DK6300000
• F: 8
• TSCA: Yes
• Hazardous Substances Data: 553-97-9(Hazardous Substances Data)

Usage

Chemical Properties

yellow to brownish crystalline powder

Uses

Different sources of media describe the Uses of 553-97-9 differently. You can refer to the following data:
1. Methyl-p-benzoquinone imine is the products were the tetrahedral adducts. Synthesis of 2H-indazole-4,7-dione derivatives from3-phenylsydnone and p-toluquinone. A Michael addition of 2-methylcyclopentane-1,3-dione to various p-toluquinone imides exclusively afforded the sole products in a regiospecific manner.
2. Methyl-p-benzoquinone (MBQ) can be used as a coating that forms an interface between the electrode and lithium (Li) electrolyte for the fabrication of redox flow batteries. It can be reduced during positive electrospray ionization mass spectroscopy (ESI MS) and can be potentially used during corona discharge.

Synthesis Reference(s)

The Journal of Organic Chemistry, 52, p. 5053, 1987 DOI: 10.1021/jo00231a048Synthetic Communications, 7, p. 467, 1977 DOI: 10.1080/00397917708050782

Safety Profile

Poison by ingestion. When heated to decomposition it emits acrid smoke and irritating fumes.

Purification Methods

Crystallise p-toluoquinone from heptane or EtOH, dry rapidly (vacuum/P2O5) and stored in a vacuum. [Beilstein 7 IV 2088.]

InChI:InChI=1/C7H6O2/c1-5-4-6(8)2-3-7(5)9/h2-4H,1H3

Upstream product

• 95-47-6 o-xylene 
• 120-66-1 N-(2-methylphenyl)acetamide 
• 546-67-8 lead(IV) tetraacetate 
• 64-19-7 acetic acid 
• 95-48-7 ortho-cresol 
• 108-38-3 m-xylene 
• 108-88-3 toluene 
• 108-44-1 1-amino-3-methylbenzene 
• 95-68-1 2,4-Xylidine 
• 100-84-5 1-methoxy-3-methyl-benzene 
• 24000-38-2 1,4-dimethoxy-1,3-butadiene 
• 95-71-6 2-methylbenzene-1,4-diol 
• 67-68-5 dimethyl sulfoxide 
• 106-51-4 p-benzoquinone 

Downstream Products

• 117360-24-4 2-methyl-5-(2-methyl-1H-indol-3-yl)benzo-1,4-quinone 
• 5462-27-1 2-methyl-4,5-di-acetoxyphenyl acetate 
• 5492-71-7 ethyl 5-hydroxy-2,6-dimethylindole-3-carboxylate 
• 2158-78-3 5-methyl-2-(N-methyl-β-hydroxyethyl)aminobenzo-1,4-quinone 
• 614-13-1 2-methoxy-5-methyl-1,4-benzoquinone 
• 137-18-8 2,5-Dimethyl-1,4-benzoquinone 
• 90111-22-1 2-methyl-6-methylsulfanyl-[1,4]benzoquinone 
• 109129-91-1 3,6-diacetoxy-2-acetylsulfanyl-toluene 
• 58-27-5 menadione 
• 1721-89-7 2,3-dimethylquinoline 
• 87970-31-8 methyl-[1,4]benzoquinone; compound with 2-methyl-hydroquinone 

Relevant articles and documents

Emitters of chemiluminescence occurring during autoxidation of substituted hydroquinones in water

A mathematical processing method for determination of spectral parameters of chemiluminescence emitters during the autoxidation of phenolic compounds in aqueous-alkaline media has been developed. The presence of a single luminescence emitter (the corresponding p-benzoquinone in the triplet state) has been demonstrated in the hydroquinone–oxygen–water system. The emitters spectra have been obtained.

Novel production process of 2-methyl-1, 4-naphthoquinone

The invention relates to the technical field of fine chemical synthesis, in particular to a novel production process of 2-methyl-1, 4-naphthoquinone. The synthesis method comprises the following stepsof: 1, oxidizing o-cresol to synthesize o-methylbenzoquinone; 2, carrying out an addition reaction on the obtained o-methylbenzoquinone and butadiene to obtain 2-methyl-1, 4-tetrahydronaphthoquinone;and 3, taking the 2-methyl-1, 4-tetrahydronaphthoquinone, and oxidizing the 2-methyl-1, 4-tetrahydronaphthoquinone with DMSO under the action of a catalyst to obtain the 2-methyl-1, 4-naphthoquinone.According to the method, the 2-methyl-1, 4-naphthoquinone product is obtained through three-step reaction by taking o-cresol as an initial raw material, the reaction raw materials are easy to obtain,the operation is simple and convenient, the method is suitable for industrial production, the synthesis cost of vitamin K3 is reduced, and the productivity and the quality are improved. The problemsthat an existing 2-methyl-1, 4-naphthoquinone synthesis process is low in yield, a used catalyst is expensive, the production cost is high, many byproducts are produced, and heavy metal ion pollutioncannot be fundamentally avoided when an inorganic salt oxidizing agent or a metal-containing catalyst is applied are solved.

Synthesis and characterization of a novel ruthenium(ii) trisbipyridine complex magnetic nanocomposite for the selective oxidation of phenols

Anchoring ruthenium(ii) trisbipyridine complex [Ru(Bpy)3]2+ into a magnetic dendritic fibrous silica nanostructure produces an unprecedented strong nanocatalyst, FeNi3/DFNS/[Ru(Bpy)3]2+. Impressive oxidation of phenols to 1,4-benzoquinones catalyzed by FeNi3/DFNS/[Ru(Bpy)3]2+ is obtained in acetonitrile and water solution with molecular dioxygen as oxidant. Exclusively, apparently inert phenols such as phenol itself and mono-alkyl-substituted phenols are impressively oxidized to produce 1,4-benzoquinones through activation of the C-H bond in the position para to the carbon-oxygen bond under mild conditions. In addition, the production of industrially significant quinones that are known intermediates for vitamin combinations is investigated and studied FeNi3/DFNS/[Ru(Bpy)3]2+ magnetic nanoparticles were produced, and their properties were investigated by AFM, FTIR, XRD, TGA, SEM, TEM, and VSM.