1131-15-3

Usage

Uses

Used in Pharmaceutical Industry:
Phenylsuccinic anhydride is used as a synthetic intermediate for the production of various pharmaceuticals. Its ability to react with different functional groups makes it a versatile building block in the development of new drugs with potential therapeutic applications.
Used in Polymer Industry:
In the polymer industry, phenylsuccinic anhydride is used as a monomer in the synthesis of hydroxypropyl methylcellulose (HPMC) esters. HPMC is a widely used excipient in the pharmaceutical industry, particularly in the formulation of controlled-release drug delivery systems. The anhydride reacts with HPMC to form esters that can improve the film-forming properties, mechanical strength, and drug release characteristics of HPMC-based formulations.
Used in Chemical Synthesis:
Phenylsuccinic anhydride is also used as a reagent in various chemical synthesis processes. Its anhydride functionality allows it to participate in a range of reactions, such as esterification, amidation, and acylation, which can lead to the formation of diverse chemical products with different applications in various industries.

InChI:InChI=1/C10H8O3/c11-9-6-8(10(12)13-9)7-4-2-1-3-5-7/h1-5,8H,6H2

Upstream product

• 635-51-8 2-phenylsuccinic acid 
• 108-31-6 maleic anhydride 
• 71-43-2 benzene 
• 4544-23-4 1-(2'-methylpropenylidene)-2-phenylcyclopropane 
• 151-50-8 potassium cyanide 
• 100-52-7 benzaldehyde 
• 105-56-6 ethyl 2-cyanoacetate 
• 96-09-3 styrene oxide 
• 201230-82-2 carbon monoxide 
• 14387-18-9 3-cyano-3-phenyl propionic acid 
• 14025-83-3 3-cyano-3-phenylpropanoic acid ethyl ester 
• 5292-53-5 diethyl benzalmalonate 
• 858197-94-1 (5-oxo-4-phenyl-5H-[2]furylidene)-phenyl-acetic acid 
• 6273-79-6 Pulvinic acid lacton 

Downstream Products

• 31591-74-9 1-(p-tolyl)-3-phenylpyrrolidine-2,5-dione 
• 22286-86-8 3,5,5-triphenyltetrahydrofuran-2(3H)-one 
• 66186-09-2 1-ethyl-3-phenyl-pyrrolidine-2,5-dione 
• 92963-62-7 2,N-diphenyl-succinamic acid 
• 109155-37-5 4-(4-methoxy-phenyl)-4-oxo-2-phenyl-butyric acid 
• 109156-67-4 4-(2-methoxy-phenyl)-4-oxo-2-phenyl-butyric acid 
• 54433-51-1 1-allyl-3-phenyl-pyrrolidine-2,5-dione 
• 86-34-0 phensuximide 
• 6307-19-3 3,4-diphenyl-4-oxobutanoic acid 
• 4370-96-1 4-oxo-2,4-diphenylbutanoic acid 
• 36122-35-7 2-phenylmaleic anhydride 
• 712-56-1 3-phenyl-succinamic acid 
• 712-57-2 (+/-)-2-phenyl-succinamic acid 
• 111030-32-1 5,5-bis-(2-chloro-phenyl)-3-phenyl-dihydro-furan-2-one 

Relevant academic research and scientific papers

Heterogeneous catalysts for the cyclization of dicarboxylic acids to cyclic anhydrides as monomers for bioplastic production

Cyclic anhydrides, key intermediates of carbon-neutral and biodegradable polyesters, are currently produced from biomass-derived dicarboxylic acids by a high-cost multistep process. We present a new high-yielding process for the direct intramolecular dehydration of dicarboxylic acids using a reusable heterogeneous Lewis acid catalyst, Nb2O5·nH2O. Various dicarboxylic acids, which can be produced by a biorefinery process, are transformed into the corresponding cyclic anhydrides as monomers for polyester production. This method is suitable for the production of renewable polyesters in a biorefinery process.

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, enantio- and diastereoselective synthesis of γ-butyrolactones incorporating quaternary stereocentres

A new, highly enantio- and diastereoselective catalytic asymmetric formal cycloaddition of aryl succinic anhydrides and aldehydes which generates paraconic acid (γ-butyrolactone) derivatives is reported.

Electrocarboxylation of alkynes with carbon dioxide in the presence of metal salt catalysts

With some common metal salts (CuI, FeCl3) as catalysts, alkynes can be effectively electrocarboxylated with CO2 (4 MPa) in an undivided cell with Ni cathode and Al sacrificial anode containing n-Bu4NBr-DMF as supporting el

Synthesis, nicotinic acetylcholine receptor binding, antinociceptive and seizure properties of methyllycaconitine analogs

A series of methyllycaconitine (1a, MLA) analogs was synthesized where the (S)-2-methylsuccinimidobenzoyl group in MLA was replaced with a (R)-2-methyl, 2,2-dimethyl-, 2,3-dimethyl, 2-phenyl-, and 2-cyclohexylsuccinimidobenzoyl (1b-f) group. The analogs 1b-f were evaluated for their inhibition of [125I]iodo-MLA binding at rat brain α7 nicotinic acetylcholine receptors (nAChR). In order to determine selectivity, MLA and the analogs 1b-f were evaluated for inhibition of binding to rat brain α,β nAChR using [3H]epibatidine. At the α7 nAChR, MLA showed a Ki value of 0.87 nM, analogs 1b-e possessed Ki values of 1.67-2.16 nM, and 1f showed a Ki value of 26.8 nM. Surprisingly, the analog 1e containing the large phenyl substituent (Ki = 1.67 nM) possessed the highest affinity. None of the compounds possessed appreciable affinity for α,β nAChRs. MLA antagonized nicotine-induced seizures with an AD50 = 2 mg/kg. None of the MLA analogs were as potent as MLA in this assay. MLA and all of the MLA analogs, with the exception of 1b, antagonized nicotine's antinociceptive effects in the tail-flick assay. Compound 1c (Ki = 1.78 nM at α7 nAChR) with an AD50 value of 1.8 mg/kg was 6.7 times more potent than MLA (AD50 = 12 mg/kg) in antagonizing nicotine's antinociceptive effects but was 5-fold less potent than MLA in blocking nicotine-induced seizures. Since MLA has been reported to show neuroprotection against β-amyloid1-42, these new analogs which have high α7 nAChR affinity and good selectivity relative to α,β nAChRs will be useful biological tools for studying the effects of α7 nAChR antagonist and neuroprotection.

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.

"ONE-POT" SYNTHESIS OF DISYMMETRICALLY α,α'-DISUBSTITUTED SUCCINIC ANHYDRIDES PRECURSORS

A "one-pot" synthesis for disymmetrically α,α'-disubstituted succinic anhydrides precursors isreported in the present paper.Substituents are aryl, primary or secondary alkyl groups.This reaction represents a simple and quick method with fair yields.

Synthesis of Small-Medium Ring Thioanhydrides

Reaction of five-membered ring anhydrides with sodium sulfide has previously been employed for synthesis of the corresponding thioanhydrides in low yields.Re-examination of the stoichiometry reveals reaction of cyclic anhydride with sodium sulfide (2:1 respectively), affords the thioanhydride accompanied by the corresponding dicarboxylate in a 1:1 molar ratio.The mechanistic pathway for this reaction has also been elucidated.Optimization of reaction conditions has resulted in the synthesis of a variety of four to seven-membered ring thioanhydride in yields approaching theoretical.

TETRAHYDROISOQUINOLINES AS ALPHA-2 ANTAGONISTS AND BIOGENIC AMINE UPTAKE INHIBITORS

The present invention provides a tetrahydroisoquinoline compound of the formula STR1 or a pharmaceutically acceptable salt thereof which is an antagonist for alpha-2 adrenoreceptors and/or which inhibits biogenic amine uptake.

The Ozonolysis of Alkenylidenecyclopropanes

The ozonolysis of alkenylidenecyclopropanes has been shown to generate cyclobutane-1,2-diones by a novel ring-expansion process which occurs at some point during oxidative cleavage of the allene unit.