53914-68-4

Basic information

• Product Name: diphenylmethyl 4-methoxybenzoate
• CAS NO: 53914-68-4
• Molecular Formula: C₂₁H₁₈O₃
• Molecular Weight: 318.3658
• Mol File: 53914-68-4.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 464.9°C at 760 mmHg
• Flash Point: 199.8°C
• Density: 1.154g/cm³
• Vapor Pressure: 8.02E-09mmHg at 25°C
• Refractive Index: 1.593
• CAS DataBase Reference: diphenylmethyl 4-methoxybenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: diphenylmethyl 4-methoxybenzoate(53914-68-4)
• EPA Substance Registry System: diphenylmethyl 4-methoxybenzoate(53914-68-4)

Safety Data

• Hazardous Substances Data: 53914-68-4(Hazardous Substances Data)

Upstream product

• 100-09-4 4-methoxybenzoic acid 
• 908093-98-1 diazodiphenylmethane 
• 91-01-0 1,1-Diphenylmethanol 
• 100-07-2 4-methoxy-benzoyl chloride 
• 5350-57-2 benzophenone hydrazone 

Relevant articles and documents

Iron(III)-catalyzed direct synthesis of diphenylmethyl esters from 2-diphenylmethoxypyridine

A highly efficient method has been developed for the synthesis of diphenylmethyl (DPM) esters from 2-diphenylmethoxypyridine. Various carboxylic acids readily reacted with 2-diphenylmethoxypyridine in the presence of FeCl3 as a catalyst to provide the desired DPM esters with high yields. The procedure is facile and enables effective synthesis of a variety of esters for the protection of carboxylic acids.

Synthesis of esters by in situ formation and trapping of diazoalkanes

A general method has been developed for the in situ formation and trapping of diazoalkanes by carboxylic acids to form esters. The method is applicable to a large variety of carboxylic acids using diazo compounds that are formed from the hydrazones of benzaldehydes and aryl ketones. In situ reaction monitoring with IR spectroscopy (ReactIR) was used to demonstrate that slow addition of the hydrazone to a mixture of oxidant and carboxylic acid avoids the buildup of the diazo compound. This method enables the safe preparation of esters from simple precursors without isolation of diazo compounds.

The Reaction between Acyl Halides and Alcohols: Alkyl Halide vs. Ester Formation

In the reaction between an acyl halide and an alcohol the thermodynamically favoured products are the free carboxylic acid and the alkyl halide.The initial reaction is, generally, the formation of an ester and HHal.When the alcohol is very prone to yield an alkyl cation upon protonation by HHal, formed H2O exhibited a superior reactivity and competed successfully with the alcohol for the acyl halide making, therefore, ester formation practically confined to a triggering role.But, in those cases where the cation is less easily formed, ester formation was favoured and, consequently, became the necessary elementary step towards alkyl halide formation.Tis final product, on the other hand, might be extremely slow to form in an SN2 reaction between the protonated ester function and the halide ion.In these instances, therefore, as well as in the cases when a basic solvent competes for the proton of HHal, the ester is the final product.A notable exception of the situation above outlined, is given by α-hydroxy-α-phenylbenzeneacetic acid (2y), which appears to undergo direct chlorine-hydroxyl interchange through a quaternary intermediate (E), in the end collapsing to α-chloro-α-phenyl-benzeneacetic acid (4y).Different systems were compared using CH2Cl2 as a solvent under strictly similar conditions.Some 28 different substrates were tested for reaction with AcCl (1a), whereas the action of eight acyl halides (a) against (RS)-α-methylbenzenemethanol (2n) and α-phenylbenzenemethanol (2p), as well as the effect of five different solvents on the reaction between two alcohols (2p and 2-methyl-2-propanol, 2c) with 1a, were observed.