55549-01-4

Basic information

• Product Name: α,α-dimethyl-o-xylene α,α'-diol
• Synonyms: α,α-dimethyl-o-xylene α,α'-diol
• CAS NO: 55549-01-4
• Molecular Weight: 166.22
• Mol File: 55549-01-4.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: α,α-dimethyl-o-xylene α,α'-diol(CAS DataBase Reference)
• NIST Chemistry Reference: α,α-dimethyl-o-xylene α,α'-diol(55549-01-4)
• EPA Substance Registry System: α,α-dimethyl-o-xylene α,α'-diol(55549-01-4)

Safety Data

• Hazardous Substances Data: 55549-01-4(Hazardous Substances Data)

Upstream product

• 87-41-2 2-benzofuran-1(3H)-one 
• 75-16-1 methylmagnesium bromide 
• 18982-54-2 o-bromobenzyl alcohol 
• 67-64-1 acetone 
• 1689-09-4 3,3-Dimethyl-3H-isobenzofuran-1-one 
• 292-64-8 Cyclooctan 
• 13387-56-9 2-(o-tolyl)propyl-2-hydroperoxide 
• 917-64-6 methyl magnesium iodide 
• 7399-49-7 1-methyl-2-(prop-1-en-2-yl)benzene 
• 577-16-2 2-Methylacetophenone 
• 7572-79-4 2-(2-methylphenyl)propan-2-ol 

Downstream Products

• 1689-09-4 3,3-Dimethyl-3H-isobenzofuran-1-one 
• 151153-41-2 1,1-dimethyl-1,3-dihydrobenzothiophene 
• 1521-94-4 1,3,3-Trimethyl-1,3-dihydro-1-isobenzofuranol 
• 21190-34-1 (2-isopropylphenyl)methanol 
• 7572-79-4 2-(2-methylphenyl)propan-2-ol 

Relevant articles and documents

Copper-catalyzed aerobic C-C bond cleavage of lactols with N-hydroxy phthalimide for synthesis of lactones

The transformation of cyclic hemiacetals (lactols) into lactones has been achieved by Cu-catalyzed aerobic C-C bond cleavage in the presence of N-hydroxy phthalimide (NHPI). The present process is composed of a multistep sequence including a) formation of exo-cyclic enol ethers by dehydration; b) addition of phthalimide N-oxyl radical to the enol ethers followed by trapping of the resulting C-radicals with molecular oxygen to form peroxy radicals; c) reductive generation of oxy radicals and subsequent β-radical fragmentation to generate lactones.

Copper-catalyzed aerobic aliphatic C-H oxygenation with hydroperoxides

We report herein Cu-catalyzed aerobic oxygenation of aliphatic C-H bonds with hydroperoxides, which proceeds by 1,5-H radical shift of putative oxygen-centered radicals (O-radicals) derived from hydroperoxides followed by trapping of the resulting carboncentered radicals with molecular oxygen.

Oxygen activation by metal complexes and alkyl hydroperoxides. Applications of mechanistic probes to explore the role of alkoxyl radicals in alkane functionalization

The mechanism of the oxidation of cycloalkanes by tertiary alkyl hydroperoxides catalysed by iron(III) dichlorotris(2-pyridylmethyl)amine IIICl2(TPA)>+ and by the acetate bridged (μ-oxo) di-iron complex III(TPA)2O(OAc)>3+ has been investigated.Product studies do not support oxidation via a high valent iron-oxo intermediate (formally FeV=O), but are consistent with a mechanism involving hydrogen atom abstraction from the alkane by alkoxyl radicals derived from the hydroperoxide.In the presence of a large excess of tert-butyl hydroperoxide, the oxidation of cyclohexane yields cyclohexanone, cyclohexanol and tert-butylcyclohexyl peroxide in more than stoichiometric amounts and, in the case of the mono-iron catalyst, one equivalent of cyclohexyl choride.Replacement of Me3COOH by hydroperoxides, which could yield tert-alkoxyl radicals having much shorter lifetimes than the tert-butoxyl radical prevents oxidation of the cycloalkane.The products obtained with these hydroperoxide mechanistic probes are those derived from the fast unimolecular reactions (generally β-scissions) of the corresponding alkoxyl radicals.The inapplicability of dimethyl sulfide as a mechanistically diagnostic trap for the putative FeV=O intermediate and the value of di-tert-butyl hyponitrite as a non-iron-based source of tert-butoxyl radicals are discussed.