76529-39-0

Basic information

• Product Name: methyl (phenylseleno)formate
• Synonyms: methyl (phenylseleno)formate
• CAS NO: 76529-39-0
• Molecular Weight: 215.11
• Mol File: 76529-39-0.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: methyl (phenylseleno)formate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (phenylseleno)formate(76529-39-0)
• EPA Substance Registry System: methyl (phenylseleno)formate(76529-39-0)

Safety Data

• Hazardous Substances Data: 76529-39-0(Hazardous Substances Data)

Upstream product

• 6294-89-9 hydrazinecarboxylic acid methyl ester 
• 6996-92-5 benzeneseleninic acid 
• 79-22-1 methyl chloroformate 
• 197724-20-2 phenylselenotris(trimethylsilyl)silane 
• 23974-72-3 sodium phenylselenide 
• 1666-13-3 diphenyl diselenide 
• 22233-91-6 phenylselenocyclohexane 

Downstream Products

• 103-25-3 3-phenylpropanoic acid methyl ester 
• 64516-63-8 3,5-diphenyl-valeric acid methyl ester 
• 6294-89-9 hydrazinecarboxylic acid methyl ester 
• 1666-13-3 diphenyl diselenide 
• 2290-03-1 methyl N'-phenylhydrazinoformate 
• 20343-90-2 bis(phenylseleno)methane 
• 68872-84-4 phenylselanyl-acetic acid methyl ester 
• 79-20-9 acetic acid methyl ester 
• 597-49-9 3-ethylpentan-3-ol 

Relevant articles and documents

An efficient, one-pot synthesis of alkyl arylselenoformates using the zinc-ruthenium chloride system in aqueous media

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Water accelerated Sm/TMSC1 reductive cleavage of the Se-Se bond: Synthesis of selenoesters and selenoformates

The reduction of diselenides by the Sm/TMSC1/H2O system led to selenide anions. These 'living' species reacted smoothly with acid chlorides, acid anhydrides and methyl chloroformate respectively to afford the desired selenoesters and selenoform

(Aryltelluro)formates as precursors of alkyl radicals: Thermolysis and photolysis of primary and secondary alkyl (aryltelluro)formates

Alkyl (aryltelluro)formates are effective precursors of oxyacyl, methyl, and primary and secondary alkyl radicals. At room temperature, irradiation of a benzene solution of methyl (aryltelluro)-formates 10-12, 2-methylpropyl (aryltelluro)formates 14 and 15, octyl (phenyltelluro)formate (17), cyclohexyl (aryltelluro)formates 19 and 20, 3β-cholestanyl (aryltelluro)formates 22 and 23, cholesteryl (phenyltelluro)formate (24) and benzyl (phenyltelluro)formate (27) with a 250-W low-pressure mercury lamp leads to the formation of oxyacyl radicals (34), which can be trapped by diphenyl diselenide to give the corresponding alkyl (phenylseleno)formates 13, 16, 18, 21, 24, 26, and 28 with excellent overall conversions. Thermolysis of these telluroformates at 160 °C in the dark leads to the formation of methyl and primary and secondary alkyl aryl tellurides 36-43 in excellent yields. Presumably, these transformations involve oxyacyl radicals, which undergo subsequent decarboxylation at the elevated temperature to afford alkyl radicals, which become involved in further radical chemistry. When 1-(benzylseleno)-5-hexyl (phenyltelluro)formate (44) was thermolysed under these conditions, 2-methylselenane (45) was observed as the sole selenium-containing product, demonstrating the synthetic utility of (aryltelluro)formates as alkyl radical precursors.