605-93-6

Usage

Chemical Properties

Yellow Solid

Uses

6-Methyl-1,4-naphthoquinone (cas# 605-93-6) is a compound useful in organic synthesis.

Upstream product

• 91-57-6 2-Methylnaphthalene 
• 5594-02-5 2-(3-methyl-2-buten-1-yl)-2,5-cyclohexadiene-1,4-dione 

Downstream Products

• 63228-95-5 2-anilino-6-methylnaphthoquinone 
• 782-23-0 2,7-dimethylanthracene 
• 3286-01-9 2,7-dimethylanthraquinone 
• 105259-46-9 6-methyl-2-thiophenyl-1,4-naphthoquinone 
• 1254329-66-2 3,4-bis(4-bromophenylamino)-7-methyl-1-pyridin-2-ylbenzo[g]isoquinoline-5,10-dione 
• 1254329-67-3 3,4-bis(4-bromophenylamino)-8-methyl-1-pyridin-2-ylbenzo[g]isoquinoline-5,10-dione 
• 81402-10-0 6-{[(p-toluenesulfonyl)oxy]methyl}-1,4-naphthoquinone 
• 81402-13-3 6-(hydroxymethyl)-1,4-naphthoquinone N-methylcarbamate 
• 81402-06-4 6-(hydroxymethyl)naphthalene-1,4-dione 
• 3837-38-5 2,6-dimethylanthracene-9,10-dione 

Relevant academic research and scientific papers

Fabrication, characterization and structure activity relationship of Co and Mn encapsulated on magnetic nanocomposite and its application in one-pot tandem synthesis of various tetrazoles and vitamin K3

Considering the importance of vitamin K3 in commercial pet foods, veterinary medicines, poultry, and some swine feed and also tetrazole derivatives in pharmacy, medicine, chemistry, petroleum, and military industry, design efficient catalytic systems are desirable. Herein, four magnetic nanocomposites (MNCs) of cobalt and manganese using metformin, 3-aminopropyltrimethoxysilane (L1) and 2-aminoethyl-3-aminopropyltrimethoxysilane (L2) were designed and constructed as an efficient and controllable catalytic system. The synthesized nanocomposites fully characterized by FT-IR, AAS, ICP-OES, BET, CHN elemental analysis, SEM, TEM, DLS, EDX, TGA, VSM, and XPS spectroscopy. The well-prepared magnetically recoverable nanocomposites were used in the synthesis of a wide derivatives of α-hydrazino tetrazoles (α-HyT), ferrocenyltetrazoles (FcT), arylaminotetrazoles (ArAT) and also vitamin K3. Besides, the effect of operating parameters, such as the amount of catalyst, nature of solvent, temperature and reaction time, metal nature, chain length and hydrophobicity properties of linkers, was studied in the catalytic efficiency of synthesized nanocatalysts. The best catalytic results were obtained in the following order: FS-L2-Met@Co(II) > FS-L2-Met@Mn(II) > FS-L1-Met@Co(II) > FS-L1-Met@Mn(II) due to their structural characteristics. In addition to high TOF, these magnetic nanocomposites are superior in easy, inexpensive, and commercially preparation, keeping the structural and magnetic characteristics, easy magnetically separation from the reaction medium, short reaction time, mild reaction condition, easy work-up, and reusability without any metal leaching in six runs. Graphical abstract: [Figure not available: see fulltext.]

Bio-inspired dimerisation of prenylated quinones directed towards the synthesis of the meroterpenoid natural products, the scabellones

Stirring 2-geranyl-6-methoxy-1,4-hydroquinone in pyridine/O2 or 2-geranyl-6-methoxy-1,4-benzoquinone in pyridine/N2 affords the dimeric meroterpenoid natural products, scabellones A-C in modest to low yields and also identifies 2-methoxy-6-(4-methylpent-3-en-1-yl)-1,4-naphthoquinone (scabellone E) as a new natural product. The corresponding reaction of the des-methoxy analogue, 2-geranyl-1,4-benzoquinone in degassed pyridine for three days afforded the natural product cordiachromene A (15% yield) and 6-(4-methylpent-3-en-1-yl)-1,4-naphthoquinone (12%), the latter being a likely biosynthetic precursor to the marine meroterpenoid alkaloids, conicaquinones A and B.

Selective oxidation of pseudocumene and 2-methylnaphthalene with aqueous hydrogen peroxide catalyzed by γ-Keggin divanadium-substituted polyoxotungstate

The catalytic performance of a γ-Keggin divanadium-substituted phosphotungstate, (Bu4N)4[γ-PW10O38V2(μ-O)(μ-OH)], has been evaluated in the selective oxidation of 1,2,4-trimethylbenzene (pseudocumene, PC) and 2-methylnaphthalene with the green oxidant, 35% aqueous hydrogen peroxide. Under conditions of H2O2 deficiency ([PC]/[H2O2] = 17-22), PC oxidation proceeded with unusually high chemo- and regioselectivity, producing exclusively 2,4,5-trimethylphenol (2,4,5-TMP) and 2,3,5-TMP in a molar ratio of 7.3/1 and a yield of 73% based on the oxidant. Isomeric 2,3,6-trimethylphenol was found in trace amounts. Under conditions of H2O2 excess ([H2O2]/[PC] = 8), 2,3,5-trimethyl-1,4-benzoquinone (TMBQ, vitamin E key intermediate) formed with 41% selectivity at 41% substrate conversion. Atypical regioselectivity was also found in the oxidation of 2-methylnaphthalene which gave predominantly 6-methyl-1,4-naphthoquinone (6-MNQ) rather than isomeric 2-MNQ. The ratio between the isomers could be altered by varying the catalyst and oxidant amounts.

Binuclear iron(III) octakis(perfluorophenyl)tetraazaporphyrin μ-oxodimer: A highly efficient catalyst for biomimetic oxygenation reactions

Binuclear iron(III) octakis(perfluorophenyl)tetraazaporphyrin μ-oxodimer complex was prepared by the reaction of bis(perfluorophenyl)maleonitrile and Fe(CO)5and tested in catalytic oxygenation reactions of several hydrocarbons in comparison with the analogous non-fluorinated phthalocyanine complexes. Results of the study demonstrate that this complex is a highly efficient catalyst for the oxygenation of anthracene, 2-tert-butylanthracene, naphthalene, 2-methylnaphthalene, phenanthrene, adamantane, and toluene using iodosylbenzene, oligomeric iodosylbenzene sulfate, or Oxone as stoichiometric oxidants.

Efficient oxidation of polycyclic aromatic hydrocarbons with H 2O2 catalyzed by 5,10,15-triarylcorrolatoiron (IV) chloride in ionic liquids

A simple and efficient oxidative system has been developed for the oxidation of polycyclic aromatic hydrocarbons with H2O2 catalyzed by 5,10,15-triarylcorrolatoiron (IV) chloride in mixed reaction media using imidazolium ionic liquids and organic solvents. The coordination effects of different organic solvents as well as anions of ionic liquids on the oxidation reactions have been examined.

Oxidation of 1,2,4-trimethylbenzene (TMB), 2,3,6-trimethylphenol (TMP) and 2-methylnaphthalene to 2,3,5-trimethylbenzoquinone (TMBQ) and menadione (vitamin K3)

The synthesis of industrially important quinones as intermediates for vitamin syntheses is reviewed with special emphasis on recent developments in our own group.

YIELD-EFFICIENT PROCESS FOR THE PRODUCTION OF HIGHLY PURE 2-METHYL-1,4-NAPHTHOQUINONE AND ITS DERIVATIVES

The present invention discloses a process for the production of 2-methyl-1,4-naphthoquinone and its bisulfite adducts, comprising the following steps: a) oxidizing 2-methyl-naphthalene (2-MNA) to achieve an organic phase containing 2-methyl-naphthoquinone (2-MNQ) and 6-methyl-naphthoquinone (6-MNQ); b) subjecting said organic phase to treatment with an aqueous solution of a bisulfite salt to extract preferentially the 6-MNQ isomer from the organic phase; c) separating said organic phase from the aqueous phase; d) subjecting the organic phase of process step c) to a second bisulfitation step with an aqueous solution of a bisulfite salt, resulting in an organic phase containing 2-MNA and trace amounts of 2-MNQ and an aqueous phase containing 2-MSB and trace amounts of 6-MSB; e) optionally removing interfering bisulfite ions from the aqueous phase of process step c); f) raising the pH of the aqueous phase from step c) or e) to higher than 8,5 in the presence of a solvent resulting in an organic phase containing 2-MNQ; g) combining the organic phase from step f) with the organic phase being treated in the process step d); h) recycling the organic phase from step d) back to step a) to be used as solvent for the oxidation reaction of 2-MNA.

Yield-efficient process for the production of highly pure 2-methyl-1,4-naphthoquinone and its derivatives

The present invention concerns a process for the production of 2-methyl-1,4-naphthoquinone and its derivatives, comprising the following steps: a) oxidizing 2-methyl-naphthalene (2-MNA) to achieve an organic phase containing 2-methyl-naphthoquinone (2-MNQ) and 6-methyl-naphthoquinone (6-MNQ); b) subjecting said organic phase to treatment with an aqueous solution of a bisulfite salt to extract preferentially the 6-MNQ isomer from the organic phase; c) separating said organic phase from the aqueous phase: d) optionally removing interfering bisulfite ions from said aqueous phase e) raising the pH of said aqueous phase to higher than 8.5 in the presence of a solvent resulting in an organic phase containing 2-MNQ; f) isolating said 2-MNQ from said organic phase.

A novel process for selective Ruthenium-Catalyzed oxidation of naphthalenes and phenols

Arenes are selectively oxidized to the corresponding quinones employing ruthenium(2,2′,6′:2″-terpyridine)(2,6-pyridinedicarboxylate) [Ru(tpy)(pydic] as catalyst and hydrogen peroxide as the terminal oxidant. Applying alkylated naphthalenes and phenols, benzo- and naphthoquinones are obtained in up to 93% yield. The industrially interesting oxidation of 2-methylnaphthalene gave 74% of the corresponding quinones and 60% of menadione (vitamin K3). 2,3,5-Trimethylbenzoquinone which constitutes the key intermediate for vitamin E is obtained in 83% yield.

Selective iron-catalyzed oxidation of phenols and arenes with hydrogen peroxide: Synthesis of vitamin e intermediates and vitamin k3

(Figure Presented). Pumping iron! Convenient iron-based catalyst systems for the selective oxidation of arenes and phenols with hydrogen peroxide to give 1, 4-quinones have been developed. This selective oxidation reaction takes place under mild conditions (room temperature, alcoholic solvents) with H 2O2 as the terminal oxidant.