102242-28-4

Basic information

• Product Name: 1(3H)-Isobenzofuranone, 3-phenyl-3-(phenylmethyl)-
• CAS NO: 102242-28-4
• Molecular Formula: C21H16O2
• Molecular Weight: 300.357
• Mol File: 102242-28-4.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 1(3H)-Isobenzofuranone, 3-phenyl-3-(phenylmethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1(3H)-Isobenzofuranone, 3-phenyl-3-(phenylmethyl)-(102242-28-4)
• EPA Substance Registry System: 1(3H)-Isobenzofuranone, 3-phenyl-3-(phenylmethyl)-(102242-28-4)

Safety Data

• Hazardous Substances Data: 102242-28-4(Hazardous Substances Data)

Upstream product

• 3532-71-6 3-hydroxy-3-phenyl-2-(p-tolyl)-2,3-dihydro-1H-inden-1-one 
• 1589-82-8 phenylmagnesium bromide 
• 85-52-9 2-Benzoylbenzoic acid 
• 85-44-9 phthalic anhydride 
• 108-88-3 toluene 
• 6621-97-2 3-hydroxy-2,3-diphenyl-1-isoindolinone 

Relevant articles and documents

Metal-Free Arylation-Lactonization Sequence of γ-Alkenoic Acids Using Anilines as Aryl Radical Precursors

The presence of salicylic acid (10 mol-%) and H2O (10 equiv.) significantly improves the arylation-lactonization sequence of γ-alkenoic acids with in situ formed diazonium salts (from bench stable anilines). The reaction is finished in less than 5 h without thermal or photochemical activation, giving access to a variety of γ,γ-disubstituted butyrolactones. The protocol is user-friendly and can be used at gram-scale or adapted to transform alkenols into phthalanes. Control experiments revealed that aryl radicals participate in the reaction and a plausible mechanism is proposed to include this and other mechanistic investigations, for the catalyzed and the background reaction.

Photoenolization as a means to release alcohols

We have designed molecules which release alcohols upon exposure to UV light independent of the reaction media, making it possible to liberate alcohols in a controlled manner in applications. Photolysis of 2-(2-isopropylbenzoyl)benzoate ester derivatives 4 in various solvents and in thin films results in the liberation of the alcohol moiety from the ester. The reaction mechanism for the release of the alcohol has been elucidated by time-resolved laser flash photolysis. Upon irradiation the triplet excited state of ketone, 4 is formed, and its lifetime can be estimated to be between 0.08 and 0.8 ns. The triplet excited state decays by efficient intramolecular H-atom abstraction to form a 1,4-biradical, 8, that has a lifetime of less than 17 ns and is trapped by molecular oxygen. In the absence of oxygen, biradical 8 intersystem crosses to form photoenols (Z)-9 and (E)-10 in a ratio of 5:2, respectively. Photoenol (Z)-9 has a lifetime of ～3000 ns in protic solvents and returns to the starting material through 1,5 intramolecular hydrogen transfer. The other isomer, (E)-10, is much longer lived (>1 ms) and releases the alcohol moiety through an intramolecular lactonization.