622-06-0

Basic information

• Product Name: 2-Butenedioic acid(Z)-bis(phenyl methyl)ester
• Synonyms: 2-Butenedioic acid(Z)-bis(phenyl methyl)ester;Maleic acid dibenzyl ester
• CAS NO: 622-06-0
• Molecular Formula: C₁₈H₁₆O₄
• Molecular Weight: 296.32
• Mol File: 622-06-0.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 420.8±25.0 °C(Predicted)
• Appearance: /
• Density: 1.187±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 2-Butenedioic acid(Z)-bis(phenyl methyl)ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Butenedioic acid(Z)-bis(phenyl methyl)ester(622-06-0)
• EPA Substance Registry System: 2-Butenedioic acid(Z)-bis(phenyl methyl)ester(622-06-0)

Safety Data

• Hazardous Substances Data: 622-06-0(Hazardous Substances Data)

Usage

Uses

Dibenzyl Maleate is an potential degradation product in over-the-counter phenylephrine containing drugs.

Upstream product

• 52267-51-3 benzyl diazoacetate 
• 63254-54-6 cyclohexyl diazoacetate 
• 35059-50-8 t-butyl diazoacetate 
• 623-73-4 diazoacetic acid ethyl ester 
• 13474-68-5 benzyl hydrogen maleate 
• 100-51-6 benzyl alcohol 
• 110-16-7 maleic acid 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 

Downstream Products

• 97678-47-2 2-Phenylsulfanyl-succinic acid dibenzyl ester 
• 538-64-7 dibenzyl fumarate 

Relevant articles and documents

Generation and Reactivity of Electron-Rich Carbenes on the Surface of Catalytic Gold Nanoparticles

The reactive nature of carbenes can be modulated, and ultimately reversed, by receiving additional electron density from a metal. Here, it is shown that Au nanoparticles (NPs) generate an electron-rich carbene on surface after transferring electron density to the carbonyl group of an in situ activated diazoacetate, as assessed by Fourier transformed infrared (FT-IR) spectroscopy, magic angle spinning nuclear magnetic resonance (MAS NMR), and Raman spectroscopy. Density functional theory (DFT) calculations support the observed experimental values and unveil the participation of at least three different Au atoms during carbene stabilization. The surface stabilized carbene shows an extraordinary stability against nucleophiles and reacts with electrophiles to give new products. These findings showcase the ability of catalytic Au NPs to inject electron density in energetically high but symmetrically allowed valence orbitals of sluggish molecules.

Photoorganocatalytic synthesis of lactones: Via a selective C-H activation-alkylation of alcohols

Selective C-H activation is an area of growing importance in modern organic chemistry. Herein, we report our efforts in combining organocatalysis and photocatalysis for the development of a highly efficient and selective visible-light mediated protocol for the C-H activation and addition of various alcohols to a plethora of Michael acceptors, followed by a cyclization reaction leading to lactones, a repeatedly occurring motif in nature. Utilizing phenylglyoxylic acid as the photocatalyst and common household bulbs as the light source, we describe a versatile α-alkylation/lactonization of alcohols with α,β-unsaturated esters leading to products in excellent yields. The reaction mechanism was extensively studied.

A mild Boc deprotection and the importance of a free carboxylate

We report a facile and rapid removal of Boc protecting groups using microwave heating in H2O, with deprotection only requiring a free carboxylic acid group in the starting material. Unlike previous approaches, no additional reagents are required.