13154-57-9

Basic information

• Product Name: 2,6-DI-TERT-BUTYL-4-METHYL-4-TERT-BUTYLPEROXY-2,5-CYCLOHEXADIENONE
• Synonyms: 2,6-DI-TERT-BUTYL-4-METHYL-4-TERT-BUTYLPEROXY-2,5-CYCLOHEXADIENONE
• CAS NO: 13154-57-9
• Molecular Formula: C₁₉H₃₂O₃
• Molecular Weight: 308.46
• Mol File: 13154-57-9.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 362.8°C at 760 mmHg
• Flash Point: 152.2°C
• Appearance: /
• Density: 0.96g/cm³
• Vapor Pressure: 1.88E-05mmHg at 25°C
• Refractive Index: 1.48
• CAS DataBase Reference: 2,6-DI-TERT-BUTYL-4-METHYL-4-TERT-BUTYLPEROXY-2,5-CYCLOHEXADIENONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-DI-TERT-BUTYL-4-METHYL-4-TERT-BUTYLPEROXY-2,5-CYCLOHEXADIENONE(13154-57-9)
• EPA Substance Registry System: 2,6-DI-TERT-BUTYL-4-METHYL-4-TERT-BUTYLPEROXY-2,5-CYCLOHEXADIENONE(13154-57-9)

Safety Data

• Hazardous Substances Data: 13154-57-9(Hazardous Substances Data)

Usage

General Description

2,6-DI-TERT-BUTYL-4-METHYL-4-TERT-BUTYLPEROXY-2,5-CYCLOHEXADIENONE is a chemical compound in the peroxyketone family, commonly used as a radical initiator in polymerization reactions. It is a highly reactive and unstable compound, commonly stored and transported in a diluted form to prevent accidental detonation. The compound is known for its strong oxidizing properties and ability to rapidly decompose when heated or exposed to light, making it suitable for initiating radical polymerization reactions. However, it is also highly hazardous and requires careful handling and storage to prevent accidents and ensure safety in industrial and laboratory settings.

InChI:InChI=1/C19H32O3/c1-16(2,3)13-11-19(10,22-21-18(7,8)9)12-14(15(13)20)17(4,5)6/h11-12H,1-10H3

Upstream product

• 75-91-2 tert.-butylhydroperoxide 
• 128-37-0 2,6-di-tert-butyl-4-methyl-phenol 
• 10396-80-2 2,6-di-tert-butyl-4-hydroxy-4-methylcyclohexa-2,5-dienone 
• 100-42-5 styrene 
• 623-73-4 diazoacetic acid ethyl ester 
• 67-63-0 isopropyl alcohol 
• 1034767-23-1 4-benzyl-3,4-dihydro-2H-benzo[b][1,4]oxazin-2-one 
• 15018-52-7 5-benzyl-1,3-dimethyl-pyrimidine-2,4,6-trione 
• 142260-70-6 1-(tert-butylperoxy)-1,2-benziodoxol-3(1H)-one 
• 3236-56-4 dipercarbonate de O,O-t-butyle 
• 6485-57-0 2,6-di-tert-butyl-4-hydroperoxy-4-methyl-2,5-cyclohexadienone 
• 75-65-0 tert-butyl alcohol 
• 3395-62-8 tert-butylperoxyl 
• 732-26-3 2,4,6-tri-tert-butylphenoxol 

Relevant articles and documents

Kharasch reaction: Cu-catalyzed and non-Kharasch metal-free peroxidation of barbituric acids

It was discovered that the Kharasch peroxidation of barbituric acids proceeds both with a Cu-catalyst and without a metal catalyst. Despite the presence of possible thermal-initiated side oxidation pathways, α-tert-butylperoxybarbiturates were selectively prepared from substituted barbituric acids and tert-butyl hydroperoxide.

Generation of Diazomethyl Radicals by Hydrogen Atom Abstraction and Their Cycloaddition with Alkenes

A general catalytic methodology for the synthesis of pyrazolines from α-diazo compounds and conjugated alkenes is reported. The direct hydrogen atom transfer (HAT) process of α-diazo compounds promoted by the tert-butylperoxy radical generates electrophilic diazomethyl radicals, thereby reversing the reactivity of the carbon atom attached with the diazo group. The regiocontrolled addition of diazomethyl radicals to carbon-carbon double bonds followed by intramolecular ring closure on the terminal diazo nitrogen and tautomerization affords a diverse set of pyrazolines in good yields with excellent regioselectivity. This strategy overcomes the limitations of electron-deficient alkenes in traditional dipolar [3+2]-cycloaddition of α-diazo compounds with alkenes. Furthermore, the straightforward formation of the diazomethyl radicals provides umpolung reactivity, thus opening new opportunities for the versatile transformations of diazo compounds.

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Peroxidation of 3,4-dihydro-1,4-benzoxazin-2-ones

The sp3-C-H peroxidation of 3,4-dihydro-1,4-benzoxazin-2-ones was achieved under mild and simple catalyst-free reaction conditions. A range of biologically important alkylated benzoxazinone peroxides are synthesized in high yield with a good functional group tolerance. The C(sp3)-OO bond was constructed efficiently and could be further converted into C(sp3)-C(sp3), C(sp3)-C(sp2), C(sp3)-C(sp), C-P and CO bonds by late-stage functional group transformations.