5416-18-2

Basic information

• Product Name: 2-methoxy-3-methylnaphthalene-1,4-dione
• Synonyms: 1,4-Naphthoquinone, 2-methoxy-3-methyl-; 2-Methoxy-3-methyl-1,4-naphthoquinone
• CAS NO: 5416-18-2
• Molecular Formula: C₁₂H₁₀O₃
• Molecular Weight: 202.206
• Mol File: 5416-18-2.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 345.5°C at 760 mmHg
• Flash Point: 154.3°C
• Density: 1.24g/cm³
• Vapor Pressure: 6.15E-05mmHg at 25°C
• Refractive Index: 1.575
• CAS DataBase Reference: 2-methoxy-3-methylnaphthalene-1,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 2-methoxy-3-methylnaphthalene-1,4-dione(5416-18-2)
• EPA Substance Registry System: 2-methoxy-3-methylnaphthalene-1,4-dione(5416-18-2)

Safety Data

• Hazardous Substances Data: 5416-18-2(Hazardous Substances Data)

Upstream product

• 186581-53-3 diazomethane 
• 483-55-6 phthiocol 
• 77-78-1 dimethyl sulfate 
• 102808-46-8 4-hydroxy-3-methoxy-2-methyl-4-phenyl-2-cyclobuten-1-one 
• 87903-65-9 3-methyl-2-(tetra-O-acetyl-β-D-glucopyranosyloxy)-1,4-naphthoquinone 
• 67-56-1 methanol 
• 58-27-5 menadione 
• 74-88-4 methyl iodide 
• 17015-99-5 2-methyl-3-chloronaphthoquinone 
• 107-30-2 chloromethyl methyl ether 
• 614-45-9 tert-Butyl peroxybenzoate 
• 2348-82-5 2-methoxy-1,4-naphthoquinone 

Relevant articles and documents

Bismuth-catalyzed methylation and alkylation of quinone derivatives with tert-butyl peroxybenzoate as an oxidant

A bismuth-catalyzed methylation of quinones in the presence of tert-butyl peroxybenzoate (TBPB) was developed via a radical reaction mechanism. Particularly, TBPB was used not only as an efficient oxidant, but also as a green methyl source in such transformation. Moreover, this method could also be efficiently extended to the alkylation of quinones. This reaction tolerated a series of functional groups and prepared a series of derivatives of vitamin K3 and benzoquinone. Notably, antimalarial parvaquone was synthesized by the reaction.

Ruthenium-catalyzed C-H oxygenation of quinones by weak O-coordination for potent trypanocidal agents

Ruthenium-catalysis enabled the C-5 selective C-H oxygenation of naphthoquinones, and also sets the stage for the site-selective introduction of a hydroxyl group into anthraquinones. A-ring modified naphthoquinoidal compounds represent an important class of bioactive quinones for which the present study encompasses the first C-H oxygenation strategy by weak O-coordination.

Organoytterbium ate complexes extend the value of cyclobutenediones as isoprene equivalents

Changing course: While organolithium and Grignard reagents favor addition to C1 of A (R=Me), the corresponding organoytterbium reagents add to C2 (R=tBu). Computational studies provide insights into the nature of organoytterbium species and their reactivity, and a total synthesis of (-)-mansonone B illustrates the utility of the method in terpenoid synthesis. Tf=trifluoromethanesulfonyl.