5442-35-3

Basic information

• Product Name: Phenol, 2,6-bis(1,1-dimethylethyl)-4-ethoxy-
• Synonyms: Phenol, 2,6-bis(1,1-dimethylethyl)-4-ethoxy-
• CAS NO: 5442-35-3
• Molecular Formula: C₁₆H₂₆O₂
• Molecular Weight: 250.38
• Mol File: 5442-35-3.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 314.6°C at 760 mmHg
• Flash Point: 84.6°C
• Appearance: /
• Density: 0.956g/cm³
• Vapor Pressure: 0.00025mmHg at 25°C
• Refractive Index: 1.494
• CAS DataBase Reference: Phenol, 2,6-bis(1,1-dimethylethyl)-4-ethoxy-(CAS DataBase Reference)
• NIST Chemistry Reference: Phenol, 2,6-bis(1,1-dimethylethyl)-4-ethoxy-(5442-35-3)
• EPA Substance Registry System: Phenol, 2,6-bis(1,1-dimethylethyl)-4-ethoxy-(5442-35-3)

Safety Data

• Hazardous Substances Data: 5442-35-3(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 78, p. 2002, 1956 DOI: 10.1021/ja01590a067

InChI:InChI=1/C16H26O2/c1-8-18-11-9-12(15(2,3)4)14(17)13(10-11)16(5,6)7/h9-10,17H,8H2,1-7H3

Upstream product

• 64-67-5 diethyl sulfate 
• 2444-28-2 2,6-di-tert-butyl-4-hydroxyphenol 
• 622-62-8 4-Ethoxyphenol 
• 115-11-7 isobutene 
• 80-40-0 ethyl ester of p-toluenesulfonic acid 
• 64-17-5 ethanol 
• 950-57-2 4-bromo-2,6-di-tert-butylcyclohexa-2,5-dienone 
• 719-22-2 2,6-Di-tert-butyl-1,4-benzoquinone 

Downstream Products

• 33768-38-6 4-ethoxy-2,6-di-tert-butyl-phenoxyl 
• 57435-51-5 C₃₈H₅₄N₂O₆ 
• 719-22-2 2,6-Di-tert-butyl-1,4-benzoquinone 
• 7722-84-1 dihydrogen peroxide 

Relevant articles and documents

Mechanistic insights into the oxidation of substituted phenols via hydrogen atom abstraction by a cupric-superoxo complex

To obtain mechanistic insights into the inherent reactivity patterns for copper(I)-O2 adducts, a new cupric-superoxo complex [(DMM-tmpa)CuII(O2?-)]+ (2) [DMM-tmpa = tris((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)amine] has been synthesized and studied in phenol oxidation-oxygenation reactions. Compound 2 is characterized by UV-vis, resonance Raman, and EPR spectroscopies. Its reactions with a series of para-substituted 2,6-di-tert-butylphenols (p-X-DTBPs) afford 2,6-di-tert-butyl-1,4-benzoquinone (DTBQ) in up to 50% yields. Significant deuterium kinetic isotope effects and a positive correlation of second-order rate constants (k2) compared to rate constants for p-X-DTBPs plus cumylperoxyl radical reactions indicate a mechanism that involves rate-limiting hydrogen atom transfer (HAT). A weak correlation of (kBT/e) ln k 2 versus Eox of p-X-DTBP indicates that the HAT reactions proceed via a partial transfer of charge rather than a complete transfer of charge in the electron transfer/proton transfer pathway. Product analyses, 18O-labeling experiments, and separate reactivity employing the 2,4,6-tri-tert-butylphenoxyl radical provide further mechanistic insights. After initial HAT, a second molar equiv of 2 couples to the phenoxyl radical initially formed, giving a CuII-OO-(ArO') intermediate, which proceeds in the case of p-OR-DTBP substrates via a two-electron oxidation reaction involving hydrolysis steps which liberate H2O2 and the corresponding alcohol. By contrast, four-electron oxygenation (O-O cleavage) mainly occurs for p-R-DTBP which gives 18O-labeled DTBQ and elimination of the R group.

SYNTHESIS OF 4-ALKOXY- AND 4-ACYLOXY-2,6-DI-tert-BUTYLPHENOLS AND QUINOL ETHERS BASED ON THEM

4-Alkoxy- and 4-acyloxy-2,6-di-tert-butylphenols were obtained by the alkylation and acylation of 2,6-di-tert-butyl-p-dihydroxybenzene.With quinone dioximes under oxidizing conditions the products form quinol ethers.