6290-94-4

Usage

Appearance

Yellowish solid powder

Physical state

Solid at room temperature

Uses

Organic synthesis, chemical reactions, production of dyes, pigments, and other organic compounds; potential use as a precursor in the synthesis of pharmaceuticals and other biologically active molecules

Aromatic properties

Unique

Potential toxicity

Yes

Irritant properties

Yes

Handling precautions

Handle with caution due to potential toxicity and irritant properties.

Upstream product

• 581-42-0 2.6-dimethylnaphthalene 
• 124-41-4 sodium methylate 
• 64-19-7 acetic acid 
• 87662-80-4 1-Hydroxy-3,7-dimethylnaphthalene 
• 51015-40-8 3,7-dimethyl-3,4-dihydronaphthalen-1(2H)-one 
• 191152-42-8 3-methyl-4-(4-methylphenyl)butanoic acid 
• 6293-55-6 2-bromo-6-methyl-[1,4]benzoquinone 
• 609-22-3 2,4-dibromo-6-methylphenol 
• 110214-23-8 2,6-dimethylnaphthalen-1-ol 
• 78-79-5 isoprene 
• 33121-78-7 3,7-dimethyl-naphthalene-2-sulfonic acid 
• 33121-71-0 2,6-dimethyl-[1]naphthoic acid 

Downstream Products

• 20490-42-0 TMN 
• 58065-58-0 2,6-dimethyl-3-phenyl-[1,4]naphthoquinone 
• 528-44-9 1,2,4-benzene tricarboxylic acid 
• 1402041-28-4 2,6-dimethyl-3-(4-(trifluoromethyl)benzyl)naphthalene-1,4-dione 
• 1402041-27-3 3-(4-bromobenzyl)-2,6-dimethylnaphthalene-1,4-dione 

Relevant academic research and scientific papers

Tunability in polyatomic molecule diffusion through tunneling versus pacing

The diffusion temperature of molecular 'walkers', molecules that are capable of moving unidirectionally across a substrate violating its symmetry, can be tuned over a wide range utilizing extension of their aromatic backbone, insertion of a second set of substrate linkers (converting bipedal into quadrupedal species), and substitution on the ring. Density functional theory simulation of the molecular dynamics identifies the motion of the quadrupedal species as pacing (as opposed to trotting or gliding). Knowledge about the diffusion mode allows us to draw conclusions on the relevance of tunneling to the surface diffusion of polyatomic organic molecules.

Anodic oxidation of methylnaphthalenes and 9-methylanthracene

Anodic methoxylation of a series of methylnaphthalenes (1-methylnaphthalene, 2-methylnaphtholene, 1,3-dimethylnaphthalene, 1,4-dimethylnaphthalene, 1,5-dimethylnaphthalene, 2,6-dimethylnaphthalene, 2,3,5-trimethylnaphthalene) and 9-methylanthracene afforded a series of nuclear-addition products. The process of nuclear addition is only observed in an aromatic ring and no chain methoxylated products were obtained. A probable mechanism is provided.

Efficient Multigram-Scale Synthesis of 7-Substituted 3-Methyltetral-1-ones and 6-Fluoromenadione

Herein, we report a safe and economical multigram synthesis of 6-fluoromenadione, an intermediate in the synthesis of novel biologically active agents. The key to this six-step sequence process involves the condensation of the readily available starting 4′-fluoropropiophenone and glyoxylic acid, a bromination-elimination sequence from 7-fluoro-3-methyltetral-1-one allowing aromatization of the naphthol intermediate, which is then oxidized into the corresponding 6-fluoromenadione. The multigram process has been demonstrated from 25 g of starting material scale with an improved overall yield of 50% and then applied to five other 7-substituted 3-methyltetralones and their corresponding 6-substituted menadiones.

A Platform of Regioselective Methodologies to Access Polysubstituted 2-Methyl-1,4-naphthoquinone Derivatives: Scope and Limitations

A platform of synthetic methodologies has been established to access a focused library of polysubstituted 3-benzylmenadione derivatives functionalized on the aromatic ring of the naphthoquinone core. Two main routes were explored: 1) The naphthol route, starting from either an α-tetralone or a propiophenone, and 2) the regioselective Diels-Alder reaction, starting from various dienes and two 2-bromo-5(or 6)-methyl-1,4-benzoquinones. 6-Substituted 2-methylnaphthols were synthesized by using a xanthate-mediated free-radical addition/cyclization sequence for the construction of the 6-substituted menadione subunit. Furthermore, an efficient and simple new pathway that allows the formation of 6- or 7-substituted 3-(substituted-benzyl)menadione regioisomers from a common commercial scaffold has also been developed by the naphthol route, advantageous with regard to step economy. Our synthetic methodologies exemplified by 34 compounds have allowed structure-activity relationships to be deduced for use as the basis for the development of new antimalarial redox-active polysubstituted benzylmenadione derivatives.

Copper-mediated oxidative trifluoromethylthiolation of quinones

A novel copper-mediated oxidative trifluoromethylthiolation of quinones was developed. This protocol provided an efficient and practical approach to a series of trifluoromethylthiolated quinones.

TOTAL SYNTHESIS OF REDOX-ACTIVE 1.4-NAPHTHOQUINONES AND THEIR METABOLITES AND THEIR THERAPEUTIC USE AS ANTIMALARIAL AND SCHISTOMICIDAL AGENTS

Naphthoquinones, azanaphthoquinones and benxanthones, their process of synthesis and their use as antimalarial or antischistosomal agents.

Total synthesis of redox-active 1.4-naphthoquinones and their metabolites and their therapeutic use as antimalarial and schistomicidal agents

Naphthoquinones, azanaphthoquinones and benxanthones, their process of synthesis and their use as antimalarial or antischistosomal agents.

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.

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.

A novel and convenient process for the selective oxidation of naphthalenes with hydrogen peroxide

A practical ruthenium phase-transfer catalyst (Ru-PTC) system for the oxidation of naphthalene derivatives has been developed. Substituted 1,4-quinones are obtained in good selectivity and yield in water without the addition of any organic solvent and acid. By applying the optimized conditions the feed additive menadione (vitamin K3) is obtained from 2-methylnaphthalene with 64 % yield and 73 % selectivity.