87742-47-0

Basic information

• Product Name: methoxymethylhydroxymethylperoxide
• Synonyms: methoxymethylhydroxymethylperoxide
• CAS NO: 87742-47-0
• Molecular Weight: 108.094
• Mol File: 87742-47-0.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: methoxymethylhydroxymethylperoxide(CAS DataBase Reference)
• NIST Chemistry Reference: methoxymethylhydroxymethylperoxide(87742-47-0)
• EPA Substance Registry System: methoxymethylhydroxymethylperoxide(87742-47-0)

Safety Data

• Hazardous Substances Data: 87742-47-0(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 78-85-3 2-methylpropenal 
• 769-60-8 2-methyl-1-phenylprop-2-en-1-one 
• 18476-73-8 (3-methylbuta-1,3-dien-2-yl)benzene 
• 98909-21-8 (1-Methoxy-2-methyl-2-propenyl)hydroperoxid 
• 98909-24-1 (1-Methoxy-1-methyl-2-phenyl-2-propenyl)hydroperoxid 
• 98909-25-2 (1-Methoxy-2-methyl-1-phenyl-2-propenyl)hydroperoxid 
• 10027-72-2 methoxymethyl hydroperoxide 
• 72572-79-3 1-methoxy-1-methyl-allyl hydroperoxide 
• 78-94-4 methyl vinyl ketone 
• 513-81-5 2,3-dimethyl-buta-1,3-diene 
• 126-99-8 chloroprene 
• 78-79-5 isoprene 

Relevant articles and documents

Products and Reaction Routes in the Diozonolysis of 2,3-Dimethyl-1,3-butadiene in Methanol

Treatment of 2,3-dimethyl-1,3-butadiene (1) with 2 molar equiv of ozone in methanol afforded the abnormal products acetic acid (12) and methyl acetate (13), which resulted from cleavage of both the double bonds and the single bond of the conjugated diene system.In model experiments it was shown that the reaction proceeds stepwise by formation of an α,β-unsaturated methoxy hydroperoxide (3) in the first and a α-keto methoxy hydroperoxide (8) in the second ozonolysis step.The latter undergoes spontaneous decomposition at ambient temperatures to give rise to the abnormal cleavage products 12 and 13.This cleavage is accompanied by emission signals in the 1H NMR spectrum which are indicative of the occurrence of acetyl radicals and hence suggest at least a partial radical-type cleavage of the α-keto methoxy hydroperoxide 8.

Diozonolyses of Acyclic Conjugated Dienes in Methanol

In the diozonolyses of isoprene (1a), 2-methyl-3-phenyl-1,3-butadiene (1b), 2,3-diphenyl-1,3-butadiene (26), and 2,3,4,5-tetramethyl-2,4-hexadiene (30) in methanol subsequent reactions of the primary cleavage products afforded abnormal products, which arose from cleavage of both the double bonds and the single bonds of the diene systems.In addition, the diozonolyses of 26 and 30 gave products, in which one of the double bonds of the respective diene system has been epoxidized.The mode of formation of the abnormal cleavage products has been elucidated by the ozonolysis of the intermediate products, viz. of α,β-unsaturated methoxyhydroperoxides and of α,β-unsaturated carbonyl compounds.

Ozonolysis of vinyl chloride in methanol: a convenient entry to methoxymethylhydroperoxide and its chemistry

Ozonolysis of vinyl chloride (7) in methanol at -78 deg C afforded methoxymethylhydroperoxide (10) in high yield along with only trace amounts of methyl formate (14).The former (10) was converted into a mixture of methyl formate (14) as the major and dimethylformal (18) as the minor product by HCl-catalysis in methanol.Reduction of 10 with dimethylsulfide and subsequent treatment with HCl-methanol gave dimethylformal (18).Partial reduction of 10 with a deficient amount of triphenylphosphine gave formaldehyde hemiacetal (19) and methoxymethylhydroxymethylperoxide (20).