19544-43-5

Basic information

• Product Name: BENZYL BUTANEDIOIC ACID ANHYDRIDE
• Synonyms: BENZYL BUTANEDIOIC ACID ANHYDRIDE;(S)-2-benzylsuccinic anhydride;2,5-Furandione, dihydro-3-(phenylMethyl)-;3-Benzyldihydrofuran-2,5-dione;DL-Benzylsuccinic anhydride;dihydro-3-(phenylmethyl)-2,5-Furandione;3-benzyloxolane-2,5-dione
• CAS NO: 19544-43-5
• Molecular Formula: C₁₁H₁₀O₃
• Molecular Weight: 190.2
• Mol File: 19544-43-5.mol
• Article Data: 13

Chemical Properties

• Melting Point: 95-97℃
• Appearance: /
• Refractive Index: 1.4980 (20℃)
• CAS DataBase Reference: BENZYL BUTANEDIOIC ACID ANHYDRIDE(CAS DataBase Reference)
• NIST Chemistry Reference: BENZYL BUTANEDIOIC ACID ANHYDRIDE(19544-43-5)
• EPA Substance Registry System: BENZYL BUTANEDIOIC ACID ANHYDRIDE(19544-43-5)

Safety Data

• Hazardous Substances Data: 19544-43-5(Hazardous Substances Data)

Usage

General Description

Benzyl butanedioic acid anhydride is a chemical compound with the molecular formula C14H12O3. It is a derivative of butanedioic acid, also known as succinic acid, and is formed by the dehydration of benzyl succinic acid. Benzyl butanedioic acid anhydride is used as a monomer for the synthesis of polymers and as a crosslinking agent in the production of resins and adhesives. It is also used in the manufacture of pharmaceuticals and agricultural chemicals. It is a white solid with a characteristic odor and should be handled with care due to its potential irritant effects.

Upstream product

• 451-40-1 phenyl benzyl ketone 
• 108-31-6 maleic anhydride 
• 23215-60-3 2-benzyl-2-phenylbenzothiazoline 
• 80459-39-8 dimethyl-2-benzylidenesuccinate 
• 100-52-7 benzaldehyde 
• 5653-88-3 2-benzylidenesuccinic acid 
• 28744-77-6 sodium diethyl-2-phenylmalonate 
• 607-81-8 diethyl 2-benzylmalonate 
• 5653-88-3 trans-phenylitaconic acid 
• 100-44-7 benzyl chloride 
• 42361-63-7 3-phenyl-propane-1,2,2-tricarboxylic acid 
• 125470-05-5 3-benzyl-4-(tert-butoxy)-4-oxobutanoic acid 
• 65859-90-7 dimethyl (E)-benzylidenesuccinate 
• 35262-43-2 dimethyl 2-benzylsuccinate 

Downstream Products

• 1613317-11-5 2-benzyl-N-[7-(4-cyclobutylthiazol-2-yl)naphthalen-2-yl]succinamic acid 
• 1216939-54-6 C₂₇H₂₁Cl₂FN₂O₃ 

Relevant articles and documents

Benzothiazolines as radical transfer reagents: Hydroalkylation and hydroacylation of alkenes by radical generation under photoirradiation conditions

Novel radical transfer reagents under photoirradiation conditions were developed by the use of benzothiazoline derivatives. These reagents enabled both hydroalkylation and hydroacylation of alkenes under neutral conditions at ambient temperature without a

Succinic anhydrides from epoxides

Catalysts and methods for the double carbonylation of epoxides are disclosed. Each epoxide molecule reacts with two molecules of carbon monoxide to produce a succinic anhydride. The reaction is facilitated by catalysts combining a Lewis acidic species with a transition metal carbonyl complex. The double carbonylation is achieved in single process by using reaction conditions under which both carbonylation reactions occur without the necessity of isolating or purifying the product of the first carbonylation.

Catalytic double carbonylation of epoxides to succinic anhydrides: Catalyst discovery, reaction scope, and mechanism

The first catalytic method for the efficient conversion of epoxides to succinic anhydrides via one-pot double carbonylation is reported. This reaction occurs in two stages: first, the epoxide is carbonylated to a β-lactone, and then the β-lactone is subsequently carbonylated to a succinic anhydride. This reaction is made possible by the bimetallic catalyst [(CITPP)Al(THF)2]+[Co(CO)4]- (1; CITPP = meso-tetra(4-chlorophenyl)porphyrinato; THF = tetrahydrofuran), which is highly active and selective for both epoxide and lactone carbonylation, and by the identification of a solvent that facilitates both stages. The catalysis is compatible with substituted epoxides having aliphatic, aromatic, alkene, ether, ester, alcohol, nitrile, and amide functional groups. Disubstituted and enantiomerically pure anhydrides are synthesized from epoxides with excellent retention of stereochemical purity. The mechanism of epoxide double carbonylation with 1 was investigated by in situ IR spectroscopy, which reveals that the two carbonylation stages are sequential and non-overlapping, such that epoxide carbonylation goes to completion before any of the intermediate β-lactone is consumed. The rates of both epoxide and lactone carbonylation are independent of carbon monoxide pressure and are first-order in the concentration of 1. The stages differ in that the rate of epoxide carbonylation is independent of substrate concentration and first-order in donor solvent, whereas the rate of lactone carbonylation is first-order in lactone and inversely dependent on the concentration of donor solvent. The opposite solvent effects and substrate order for these two stages are rationalized in terms of different resting states and rate-determining steps for each carbonylation reaction.