93011-75-7

Basic information

• Product Name: Benzoic acid, 2-(2-propenyloxy)-, phenyl ester
• CAS NO: 93011-75-7
• Molecular Formula: C16H14O3
• Molecular Weight: 254.285
• Mol File: 93011-75-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Benzoic acid, 2-(2-propenyloxy)-, phenyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoic acid, 2-(2-propenyloxy)-, phenyl ester(93011-75-7)
• EPA Substance Registry System: Benzoic acid, 2-(2-propenyloxy)-, phenyl ester(93011-75-7)

Safety Data

• Hazardous Substances Data: 93011-75-7(Hazardous Substances Data)

Upstream product

• 118-55-8 phenyl Salicylate 
• 106-95-6 allyl bromide 

Downstream Products

• 132-64-9 dibenzofuran 
• 108-95-2 phenol 

Relevant articles and documents

Formation of dibenzofurans by flash vacuum pyrolysis of aryl 2-(allyloxy)benzoates and related reactions

Flash vacuum pyrolysis (FVP) of aryl 2-(allyloxy)benzoates 5 and of the corresponding aryl 2-(allylthio)benzoates 6 at 650°C, gives dibenzofurans 19 and dibenzothiophenes 20, respectively. The mechanism involves generation of phenoxyl (or thiophenoxyl) radicals by homolysis of the O-allyl (or S-allyl) bond, followed by ipso attack at the ester group, loss of CO2 and cyclisation of the resulting aryl radical. Synthetically, the procedure works well for p-substituted substrates, which lead to 2-substituted dibenzofurans 19b-f (73-90%) and dibenzothiophenes 20b-c (90-94%). Little selectivity is shown in the cyclisation of m-substituted substrates and competing interactions of the radical with the substituent - and ipso-attack - complicate the pyrolyses of o-substituted substrates. FVP of related radical precursors including 2-(allyloxy)phenyl benzoates 43 gave no dibenzofurans, whereas 2-(allyloxy-5-methyl)azobenzene 44 gave a much reduced yield. No carbazoles were obtained by FVP of 4-methylphenyl 2-(allylamino)benzoate 42.