16404-66-3

Basic information

• Product Name: 4-hydroxy-2,4,6-trimethylcyclohexa-2,5-dien-1-one
• CAS NO: 16404-66-3
• Molecular Formula: C₉H₁₂O₂
• Molecular Weight: 152.1904
• Mol File: 16404-66-3.mol
• Article Data: 32

Chemical Properties

• Boiling Point: 273.1°C at 760 mmHg
• Flash Point: 114°C
• Density: 1.08g/cm³
• Vapor Pressure: 0.000751mmHg at 25°C
• Refractive Index: 1.516
• CAS DataBase Reference: 4-hydroxy-2,4,6-trimethylcyclohexa-2,5-dien-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4-hydroxy-2,4,6-trimethylcyclohexa-2,5-dien-1-one(16404-66-3)
• EPA Substance Registry System: 4-hydroxy-2,4,6-trimethylcyclohexa-2,5-dien-1-one(16404-66-3)

Safety Data

• Hazardous Substances Data: 16404-66-3(Hazardous Substances Data)

Upstream product

• 527-61-7 2,6-dimethyl-1,4-benzoquinone 
• 917-54-4 methyllithium 
• 527-60-6 Mesitol 
• 71-36-3 butan-1-ol 
• 111-27-3 hexan-1-ol 
• 108-67-8 1,3,5-trimethyl-benzene 
• 18052-51-2 trimethyl(2,4,6-trimethylphenoxy)silane 
• 4380-68-1 2,4,6-trimethylbenzamide 
• 75-75-2 methanesulfonic acid 
• 603-71-4 nitromesitylene 
• 75-65-0 tert-butyl alcohol 
• 67-63-0 isopropyl alcohol 
• 107-18-6 allyl alcohol 
• 71-41-0 pentan-1-ol 

Downstream Products

• 49583-05-3 3-acetoxy-2,4,6,trimethylphenyl acetate 
• 700-13-0 Trimethylhydroquinone 
• 1349842-30-3 tert-butyl (1,3,5-trimethyl-4-oxocyclohexa-2,5-dien-1-yl) malonate 
• 1217509-73-3 1,3,5-trimethyl-4-oxocyclohexa-2,5-dienyl 6-O-acetyl-2-deoxy-2-iodo-3,4-O-(1-methylethylidene)-β-D-galactopyranoside 
• 2233-18-3 4-hydroxy-3,5-dimethylbenzaldehyde 
• 527-61-7 2,6-dimethyl-1,4-benzoquinone 
• 33919-00-5 4-hydroperoxy-2,4,6-trimethyl-2,5-cyclohexadien-1-one 
• 527-60-6 Mesitol 
• 854726-50-4 4-hydroxy-2,4,6-trimethyl-5-phenyl-cyclohex-2-enone 
• 99647-82-2 2,4,6-trimethyl-3-hydroxybiphenyl 
• 70328-76-6 1-acetoxy-2,3,4,6-tetramethylbenzene 

Relevant articles and documents

Singlet oxygen generation from H2O2/MoO42-: Peroxidation of hydrophobic substrates in pure organic solvents

Seventeen organic solvents are screened as reaction media to conduct the molybdate-catalyzed disproportionation of hydrogen peroxide into singlet molecular oxygen, 1O2 (1Δg). The solvents are investigated by resorting to the detection of the infra-red luminescence of 1O2 at 1270 nm. Preparative peroxidations of representative substrates are carried out in the most efficient ones. The latter are protic and polar and constitute a simpler alternative to the well suited but more intricate microemulsion systems for the peroxidation of hydrophobic substrates with chemically generated 1O2.

PhSeBr mediated hydroxylative oxidative dearomatization of naphthols-an open air facile one-pot synthesis of ketols

A new methodology for oxidative-dearomatization of planar phenols is described. An economic, viable one-pot metal free protocol for direct conversion of naphthols to α-ketols is reported. Naphthols were found to undergo facile unprecedented oxidative dearomatization with regioselective hydroxylation with phenyl selenyl bromide in open air conditions. Quaternary stereocenters were developed along with formation of sterically demanding α- and γ-ketols with high yields. Functional group tolerance like esters is revealed. A thorough study of the stereoelectronic demands of the unusual oxy-selenium reactive intermediate involved in dearomatization of 1- and 2-naphthols is carried out. 4-Hydroxy cyclohexadieneone and cyclohexadieneone aryl ethers were generated from dialkyl-phenols under similar reaction conditions providing direct evidence of the mechanical postulate. The first instance of the phenoxy-selenium interaction leading to facile dearomatization of arenes is highlighted in this manuscript.

Singlet Oxygen Generation from a Water-Soluble Hypervalent Iodine(V) Reagent AIBX and H2O2: An Access to Artemisinin

Herein, we report an efficient method for the chemical generation of 1O2 by treatment of H2O2 with AIBX, a highly water-soluble, bench-stable, recyclable hypervalent iodine(V) reagent developed by our group. The generation of 1O2 was confirmed by the following results: (1) capture of 1O2 with the sodium salt of anthracene-9,10-bis(ethanesulfonate) produced the corresponding endoperoxide and (2) TEMPO (2,2,6,6-tetramethyl-1-piperidinyloxy) produced by the oxidation of 2,2,6,6-tetramethylpiperidine with 1O2 generated using the AIBX/H2O2 system was detected by electron spin resonance spectroscopy. To illustrate the potential utility of this method for organic synthesis, we used the AIBX/H2O2 system to perform typical reactions of 1O2: [2 + 2]/[4 + 2] cycloadditions, Schenck ene reactions, and heteroatom oxidation reactions, which afforded the corresponding products in high yields. Moreover, we used the method to synthesize the antimalarial drug artemisinin. Finally, we demonstrated that AIBX could be regenerated after the reaction by means of a workup involving extraction and removal of water to obtain a precursor of AIBX, which could then be re-oxidized.

Reductive Aromatization of Quinols with B2pin2 as Deoxidizing Agent

We have demonstrated B2pin2 as superior deoxidizing agent for the reductive deoxygenation of quinol derivatives under basic conditions. A wide range of highly functionalized phenols were obtained in good yields including a complex drug molecule, which revealed the high functional group tolerance of this protocol.

Site-selective Oxidative Dearomatization of Phenols and Naphthols into ortho-Quinols or Epoxy ortho-Quinols using Oxone as the Source of Dimethyldioxirane

A novel reactivity of dimethyldioxirane, generated in situ from Oxone and acetone, with substituted phenols and naphthols is reported. This methodology allowed the synthesis of ortho-quinols or epoxy ortho-quinols from a site-selective oxidative dearomatization process, with good yields under very mild conditions. A short total synthesis of natural product lacinilene C methyl ether is also described using this process as the key step. (Figure presented.).