58241-12-6

Basic information

• Product Name: phenyl diphenylacetate
• Synonyms: phenyl diphenylacetate
• CAS NO: 58241-12-6
• Molecular Formula: C₂₀H₁₆O₂
• Molecular Weight: 288.33984
• Mol File: 58241-12-6.mol

Chemical Properties

• Boiling Point: 448.4°Cat760mmHg
• Flash Point: 142.4°C
• Appearance: /
• Density: 1.146g/cm³
• Vapor Pressure: 3.12E-08mmHg at 25°C
• Refractive Index: 1.603
• CAS DataBase Reference: phenyl diphenylacetate(CAS DataBase Reference)
• NIST Chemistry Reference: phenyl diphenylacetate(58241-12-6)
• EPA Substance Registry System: phenyl diphenylacetate(58241-12-6)

Safety Data

• Hazardous Substances Data: 58241-12-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C20H16O2/c21-20(22-18-14-8-3-9-15-18)19(16-10-4-1-5-11-16)17-12-6-2-7-13-17/h1-15,19H

Upstream product

• 3469-17-8 2-diazo-1,2-diphenylethan-1-one 
• 108-95-2 phenol 
• 1871-76-7 diphenylacetic acid chloride 
• 117-34-0 2,2-diphenylacetic acid 
• 32354-35-1 C₆H₅ORh(CO)(P(C₆H₅)3)2 
• 139-02-6 sodium phenoxide 
• 857788-00-2 chloro-diphenyl-acetaldehyde diphenylacetal 
• 860511-43-9 hydroxy-diphenyl-acetaldehyde diphenylacetal 
• 57985-02-1 ethyl diphenyloxyacetate 
• 538-75-0 dicyclohexyl-carbodiimide 
• 68423-83-6 diphenyl-ketene-diphenylacetal 
• 10035-10-6 hydrogen bromide 
• 64-19-7 acetic acid 
• 56-23-5 tetrachloromethane 

Downstream Products

• 574-45-8 N-(diphenylmethylidene)phenylamine 
• 18677-34-4 benzhydryltriethylsilane 
• 4930-03-4 phenyl N-phenylcarbamate 
• 103-71-9 phenyl isocyanate 
• 108-95-2 phenol 

Relevant articles and documents

Iodobenzene Dichloride in the Esterification and Amidation of Carboxylic Acids: In-Situ Synthesis of Ph3PCl2

A novel, in-situ synthesis of dichlorotriphenylphosphorane (Ph3PCl2) is accomplished upon combining PPh3and the easily prepared hypervalent iodine reagent iodobenzene dichloride (PhICl2). The phosphorane is selectively generated in the presence of carboxylic acid or alcohol residues to rapidly produce acyl chlorides and alkyl chlorides in high yields. Addition of EtOH, PhOH, BnOH, Et2NH or CH2N2results in the direct synthesis of esters, amides and diazo ketones from carboxylic acids.

Effective esterification of carboxylic acids using (6-oxo-6H-pyridazin-1-yl)phosphoric acid diethyl ester as novel coupling agents

(6-Oxo-6H-pyridazin-1-yl)phosphoric acid diethyl esters (3) are efficient and selective coupling agents for equimolar esterification of carboxylic acids and alcohols. Esterification of aliphatic and aromatic carboxylic acids with aliphatic and aromatic alcohols using 3 afforded the corresponding esters chemoselectively in good to excellent yield.

Selective esterifications of alcohols and phenols through carbodiimide couplings

Esterification of carboxylic acids capable of forming ketene intermediates upon treatment with carbodiimides permits the selective acylation of alcohols in the presence of phenols lacking strong electron-withdrawing groups. The selectivity of acylations involving highly acidic phenols could be reversed through the addition of catalytic amount of acid. Esterification of other carboxylic acids was found to proceed through the formation of symmetric anhydrides and provide the opposite chemoselectivity. In both cases the relative acylation rates of substituted phenols are consistent with a reaction mechanism involving an attack of phenolate anions on electrophilic intermediates such as ketenes and symmetric anhydrides, with the carbodiimides serving both as an activating reagent and as a basic catalyst.

Mechanism of hydrolysis of coumaran-2-ones

The hydrolysis of coumaran-2-one and 5-substituted 3-phenylcoumaran-2-ones is preceded by a pre-equilibrium involving the formation of an enolate anion at high pH. The pKa of 3-phenylcoumaran-2-one is 8.39 in water at 25°C and the 3-phenyl subs

Carbon-oxygen bond formation on rhodium centers. Synthesis, characterization, crystal structure, and reactions of trans-PhORh(CO)(PPh3)2

The synthesis of a rhodium phenoxide is reported. The complex trans-PhORh(CO)(PPh3)2 crystallizes in the centrosymmetric monoclinic space group P21/c with a = 15.794 (3) ?, b = 11.449 (2) ?, c = 20.025 (3) ?, β = 100.220 (13)°, V = 3562 (1) ?3, and Z = 4. Diffraction data (Mo Kα, 2θ = 4.5-50.0°) were collected with a Syntex P21 diffractometer, and the structure was refined to RF = 2.8% for 5293 reflections. The structure is isomorphous with the iridium analogue. Important dimensions include Rh-P = 2.337 (1)-2.357 (1) ?, Rh-CO = 1.801 (3) ?, Rh-OPh = 2.044 (2) ?, and Rh-O-C(phenoxide) = 125.52 (19)°. This complex reacts with Ph2CHC(O)Cl to give the ester Ph2CHC(O)OPh and with MeI to give anisole, PhOMe. The formation of anisole from the rhodium phenoxide is in contrast to the failure to eliminate ethers from similar iridium complexes and is consistent with the known preference for elimination from second-row (rather than third-row) transition-metal complexes.

The Chemistry of Pentavalent Organobismuth Reagents. Part 8. Phenylation and Oxidation of Alcohols by Tetraphenylbismuth Esters

Tetraphenylbismuth trifluoroacetate under neutral or slightly acidic conditions O-phenylates primary alcohols in reasonable (65-75percent) yield, but gives only moderate yields with secondary alcohols and no O-phenylation with tertiary alcohols.An SN2 type mechanism is proposed with attack of oxygen on aryl carbon.In contrast, the reaction of Bi(V) reagents with alcohols under basic conditions gives, exclusively, oxidation, often with benzene as a leaving group.The presence of a Bi(V) intermediate with a bismuth-oxygen bond has been proved in several different ways using n.m.r. spectroscopy.Thus the reactions of alcohols with Bi(V) reagents parallel the corresponding reactions with phenols.