110450-40-3

Basic information

• Product Name: 2-Propynoic acid, 4-methylphenyl ester
• CAS NO: 110450-40-3
• Molecular Formula: C10H8O2
• Molecular Weight: 160.172
• Mol File: 110450-40-3.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2-Propynoic acid, 4-methylphenyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Propynoic acid, 4-methylphenyl ester(110450-40-3)
• EPA Substance Registry System: 2-Propynoic acid, 4-methylphenyl ester(110450-40-3)

Safety Data

• Hazardous Substances Data: 110450-40-3(Hazardous Substances Data)

Upstream product

• 106-44-5 p-cresol 
• 471-25-0 Propiolic acid 

Downstream Products

• 1315362-81-2 (E)-p-tolyl 3-(2-amino-3-oxo-2,3-dihydrobenzofuran-2-yl)acrylate 
• 92-48-8 6-methylcoumarin 
• 110450-47-0 1-(2-hydroxy-5-methylphenyl)propynone 

Relevant articles and documents

How much does the hybridization of a carbon atom affect the transmission of the substituent effect on the chemical shift?

1H and 13C NMR spectra of aryl esters of propionic acid, acrylic acid, and propiolic acid were systematically examined to find out the substituent effect on the chemical shift. The values of the chemical shift of the carbonyl carbon showed an inverse correlation with the Hammett ?3 values, and the magnitude of the slope was the largest with the propiolates. The ?± carbons of acrylates and propiolates also showed an inverse correlation with much smaller values of the slopes than those of the carbonyl carbons; but those of the propionates showed absolutely no correlation. However, the ?2 carbons of acrylates and propiolates showed normal correlation with larger values of the slopes. The signs and the magnitudes of the slopes may be understood by the transmission of the substituent electronic effect through bonds as well as through space. The propiolyloxy group also showed a significantly large effect on the 13C chemical shift values of the benzene ring.

New photochemical approaches to the synthesis of chromones

Irradiation of the p-methoxyphenyl and p-methylphenyl esters of 2-butynoic, propynoic, 3-(ethylenedioxy)butanoic, 3,3-dimethoxypropanoic and 3-oxobutanoic acids (1-3) affords the corresponding photo-Fries products 4-6. Compound 5a is converted in part into the acetophenone 7a, by way of a Norrish type II photo-reaction, while compound 6a is reluctant to undergo this process, in spite of the fact that it also possess γ-carbonyl hydrogen atoms. From the preparative point of view, the photorearrangement of the esters 1a-d and 2a,c-d is exploitable, while that of 3a proceeds with a lower yield. The differences found in the photochemical behaviour of 2a and 3a show the sharp influence of the acetal group on the course of the reaction. Compounds 4-6 are representative model compounds valuable as direct chromone precursors; in fact, they can be readily cyclized to the chromones 10 under basic or acidic conditions.