134339-50-7

Basic information

• Product Name: GAMMA-PHENYL-EPSILON-CAPROLACTONE
• Synonyms: γ-Phenyl-ε-caprolactone
• CAS NO: 134339-50-7
• Molecular Formula: C₁₂H₁₄O₂
• Molecular Weight: 190.24
• Product Categories: Building Blocks;Carbonyl Compounds;Chemical Synthesis;Lactones;Organic Building Blocks
• Mol File: 134339-50-7.mol
• Article Data: 21

Chemical Properties

• Boiling Point: 354.485°C at 760 mmHg
• Flash Point: 147.887°C
• Appearance: /
• Density: 1.081g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.524
• Storage Temp.: 2-8°C
• CAS DataBase Reference: GAMMA-PHENYL-EPSILON-CAPROLACTONE(CAS DataBase Reference)
• NIST Chemistry Reference: GAMMA-PHENYL-EPSILON-CAPROLACTONE(134339-50-7)
• EPA Substance Registry System: GAMMA-PHENYL-EPSILON-CAPROLACTONE(134339-50-7)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• Hazardous Substances Data: 134339-50-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C12H14O2/c13-12-7-6-11(8-9-14-12)10-4-2-1-3-5-10/h1-5,11H,6-9H2

Upstream product

• 4894-75-1 1-phenyl-4-cyclohexanone 

Downstream Products

• 5354-04-1 4-phenylhexanoic acid 
• 1391860-11-9 3-phenylhexane-1,6-diol 
• 176101-44-3 methyl 4-phenyl-5-hexenoate 
• 96746-40-6 4-phenyl-5-hexen-1-ol 
• 168208-59-1 methyl (E)-8-<(tert-butyldimethylsilyl)oxy>-6-phenyloct-2-enoate 
• 168208-42-2 (Z)-8-(tert-Butyl-dimethyl-silanyloxy)-6-phenyl-oct-2-enoic acid methyl ester 
• 168208-60-4 tert-Butyl-((E)-8-chloro-3-phenyl-oct-6-enyloxy)-dimethyl-silane 
• 168208-57-9 (Z)-8-chloro-3-phenyl-1-<(tert-butyldimethylsilyl)oxy>oct-6-ene 
• 168208-48-8 (E)-8-<(tert-butyldimethylsilyl)oxy>-6-phenyloct-2-enol 
• 168208-45-5 (Z)-8-<(tert-butyldimethylsilyl)oxy>-6-phenyloct-2-enol 
• 168208-44-4 methyl 1-<(tert-butyldimethylsilyl)oxy>-3-phenyloct-6-yn-8-oate 
• 168208-41-1 tert-Butyl-(7,7-dibromo-3-phenyl-hept-6-enyloxy)-dimethyl-silane 
• 168208-40-0 6-(tert-Butyl-dimethyl-silanyloxy)-4-phenyl-hexanal 
• 553670-95-4 7-benzenesulfinyl-4-phenyl-2,3,4,5-tetrahydrooxepine 

Relevant articles and documents

Baeyer-Villiger oxidation under Payne epoxidation conditions

A novel method for the Baeyer-Villiger oxidation of ketones has been developed and optimized. The transformation involves a transition metal-free activation of hydrogen peroxide under Payne epoxidation conditions. Reaction of a ketone with hydrogen peroxide in the presence of a nitrile under mildly basic reaction conditions leads to the corresponding ester. The transformation has been successfully applied to a range of ketones in moderate to excellent yields (30-91%) and good to excellent regioselectivities (7:1 to 20:1).

A robust chemo-enzymatic lactone synthesis using acyltransferase from Mycobacterium smegmatis

The new application of acyltransferase, isolated from Mycobacterium smegmatis for the chemo-enzymatic Baeyer-Villiger oxidation of cyclic ketones to lactones was demonstrated. Acyltransferase exhibited high activity, and high stability under harsh reaction conditions, like oxidation with 60% aq. H2O2 at 45°C. This paves the way to a novel robust chemo-enzymatic method for lactone synthesis with high yields.

Perdecanoic acid as a safe and stable medium-chain peracid for Baeyer-Villiger oxidation of cyclic ketones to lactones

Stability studies dedicated to high-energy compounds for a series of linear peracids (C6-C12), including sensitivity to mechanical impulse (shock and friction), as well as electrical (spark) and thermal sensitivity (temperature and heat of decomposition), were presented in this work for the first time. Studies revealed that all peracids were insensitive to shock, while in the case of the other sensitivity tests sharp differences between results for C8 and C10 peracids were observed. Taking into account the relatively high initial temperature of decomposition (above 64 °C) perdecanoic acid was selected as a safe alternative to commonly used hazardous short-chain peracids. Next, a new method for the Baeyer-Villiger oxidation was presented. Oxidation of 2-adamantanone was chosen as a model reaction. Peroctanoic, perdecanoic and perdodecanoic acids were tested as oxidants. Peroctanoic acid was the most reactive but taking into account both safety and kinetic issues, perdecanoic acid was selected for the further studies. The influence of reaction conditions on reaction rate was investigated. Optimized reaction conditions were suggested (two-fold molar excess of peracid with respect to the ketone, toluene as a solvent, 35 °C). This exploratory study offers promise with regard to the development of safer alternatives to peracetic acid in industrial oxidation.

Titanium complexes of pyrrolylaldiminate ligands and their exploitation for the ring-opening polymerization of cyclic esters

A series of six-coordinate titanium complexes1-6supported by pyrrolylaldiminate ligands were preparedviathe reaction of 2 equivalents of ligands and Ti(OiPr)4in toluene at 70 °C. The X-ray structure of2revealed that the two ligands w