103-43-5

Basic information

• Product Name: DIBENZYL SUCCINATE
• Synonyms: TIMTEC-BB SBB006245;SUCCINIC ACID DIBENZYL ESTER;SPASMINE;Butanedioic acid, bis(phenylmethyl) ester;BENZYL SUCCINATE;DIBENZYL SUCCINATE;butanedioic acid dibenzyl ester;DIBENZYL ETHANE-1,2-DICARBOXYLATE
• CAS NO: 103-43-5
• Molecular Formula: C₁₈H₁₈O₄
• Molecular Weight: 298.33
• EINECS: 203-110-9
• Product Categories: Pharmaceutical Intermediates
• Mol File: 103-43-5.mol

Chemical Properties

• Melting Point: 42-43°C
• Boiling Point: 245°C/15mm
• Flash Point: 245°C/15mm
• Appearance: /
• Density: 1.256
• Vapor Pressure: 3.82E-07mmHg at 25°C
• Refractive Index: 1.5960
• Water Solubility: Insoluble in water.
• BRN: 1916056
• CAS DataBase Reference: DIBENZYL SUCCINATE(CAS DataBase Reference)
• NIST Chemistry Reference: DIBENZYL SUCCINATE(103-43-5)
• EPA Substance Registry System: DIBENZYL SUCCINATE(103-43-5)

Safety Data

• Safety Statements: S22:Do not inhale dust.; S24/25:Avoid contact with skin and eyes.
• Hazardous Substances Data: 103-43-5(Hazardous Substances Data)

Usage

Uses

Used in Organic Chemical Synthesis:
Dibenzyl succinate is used as an organic chemical synthesis intermediate for the production of a wide range of compounds. Its unique structure allows it to be a valuable building block in the creation of various organic molecules, contributing to the development of new materials and chemicals.
Used in Medicine (Antispasmodic):
In the medical field, dibenzyl succinate is utilized as an antispasmodic agent. It helps to relieve muscle spasms and cramps, providing relief to patients suffering from various conditions that cause involuntary muscle contractions. Its effectiveness in this application is attributed to its ability to interact with the muscles and nerves, thereby reducing the frequency and intensity of spasms.

InChI:InChI=1/C18H18O4/c19-17(21-13-15-7-3-1-4-8-15)11-12-18(20)22-14-16-9-5-2-6-10-16/h1-10H,11-14H2

Upstream product

• 108-30-5 succinic acid anhydride 
• 100-51-6 benzyl alcohol 
• 150-90-3 sodium succinate 
• 100-44-7 benzyl chloride 
• 543-20-4 succinoyl dichloride 
• 110-15-6 succinic acid 
• 103-83-3 N,N'-dimethylbenzylamine 
• 106-65-0 Dimethyl succinate 
• 111-20-6 1,10-decanedioic acid 
• 500-32-3 N-benzyl-N,N-dimethyl-anilinium; dimethylphenylbenzylammonium hydroxide 
• 100-39-0 benzyl bromide 
• 620-05-3 iodomethylbenzene 
• 140-11-4 Benzyl acetate 
• 74-85-1 ethene 

Downstream Products

• 103-40-2 succinic acid monobenzyl ester 
• 6946-88-9 3-(propoxycarbonyl)propanoic acid 
• 925-15-5 dipropyl succinate 
• 1350373-51-1 3-((benzyloxy)carbonyl)-5-methylhex-3-enoic acid 
• 1350373-52-2 3-((benzyloxy)carbonyl)-5-methylhex-3-enoic acid ethyl ester 

Relevant articles and documents

Palladium–Bis(carbene) Catalysts for the Bisalkoxycarbonylation of Olefins to Succinic Diesters

A series of Pd-bis(NHC) (NHC = N-heterocyclic carbene) complexes possessing various anions and substituents were used in the bisalkoxycarbonylation of olefins (α-olefins and ethylene) to afford industrially useful succinic diesters in modest to good yields. The influence of different ligands and counteranions of the Pd complexes on their catalytic activity was assessed, and it was found that dimeric Pd–bis(NHC)Br was the best catalyst for the bisalkoxycarbonylation reactions. The structure of dimeric Pd–bis(NHC)Br was confirmed by X-ray crystallographic analysis.

Esterification of bio-based succinic acid in biphasic systems: Comparison of chemical and biological catalysts

Different chemical and biological catalysts were screened for the biphasic esterification of aqueous solutions of succinic acid with 1-octanol. Among them, DBSA, Nafion NR-50 and Novozym 435 were found to be the most attractive catalysts. The pH, the temperature and the catalyst concentration had high impacts on the reaction rates. The optimization of the reaction conditions with a single-variable approach for the chemical catalysts and a Response Surface Methodology for the enzyme allowed an increase of the rates by a factor 1.5 for DBSA, 2.3 for Nafion NR-50 and 1.3 for Novozym 435. Real fermentation broths produced from recombinant Escherichia coli could be successfully esterified with conversions up to 93% for DBSA and 70% for Nafion NR-50 and Novozym 435 as catalysts. Finally, DBSA was selected as the cheapest and most active option. Besides, the esters were isolated with a purity of 83% from fermentation broth solutions. DBSA also catalyzed the esterification of succinic acid from fermentation broth with many alcohols creating a broad spectrum of interesting esters. The esters might then be used as end-product, hydrolyzed back to pure succinic acid or hydrogenated.

ZWITTERIONIC CATALYSTS FOR (TRANS)ESTERIFICATION: APPLICATION IN FLUOROINDOLE-DERIVATIVES AND BIODIESEL SYNTHESIS

An amide/iminium zwitterion catalyst has a catalyst pocket size that promotes transesterification and dehydrative esterification. The amide/iminium zwitterions are easily prepared by reacting aziridines with aminopyridines. The reaction can be applied a wide variety of esterification processes including the large-scale synthesis of biodiesel. The amide/iminium zwitterions allow the avoidance of strongly basic or acidic condition and avoidance of metal contamination in the products. Reactions are carried out at ambient or only modestly elevated temperatures. The amide/iminium zwitterion catalyst is easily recycled and reactions proceed in high to quantitative yields.

A Mild, General, Metal-Free Method for Desulfurization of Thiols and Disulfides Induced by Visible-Light

A visible-light-induced metal-free desulfurization method for thiols and disulfides has been explored. This radical desulfurization features mild conditions, robustness, and excellent functionality compatibility. It was successfully applied not only to the desulfurization of small molecules, but also to peptides.

Amide/Iminium Zwitterionic Catalysts for (Trans)esterification: Application in Biodiesel Synthesis

A class of zwitterionic organocatalysts based on an amide anion/iminium cation charge pair has been developed. The zwitterions are easily prepared by reacting aziridines with aminopyridines. They are catalytically applicable to transesterifications and dehydrative esterifications. Mechanistic studies reveal that the amide anion and iminium cation work synergistically in activating the reaction partners, with the iminium cationic moiety interacting with the carbonyl substrates through nonclassical hydrogen bonding. The reaction can be applied to large-scale synthesis of biodiesel under mild conditions.

Desulfurization method of organic compounds containing mercapto or disulfide bond

The invention relates to a desulfurization method of organic compounds, in particular, organic compounds containing mercapto or a disulfide bond. The method comprises following steps: dissolving organic compounds containing mercapto or a disulfide bond by a solvent; adding a phosphine reagent and an initiator; and carrying out reactions in the presence of light to convert the substrate into corresponding desulfurization products. The organic compounds containing mercapto or a disulfide bond is R-SH or R-S-S-R; wherein R represents a primary carbon group, a secondary carbon group, a tertiary carbon group, an aryl group, or an acyl group. The reactions do not need any metal, and the reaction conditions are mild. Moreover, the desulfurization method has the advantages of high yield, wide substrate application range, and multiple suitable solvents, and is widely suitable for multiple kinds of mercapto-removing reactions and desulfurization reactions of disulfide.

IMPROVED SYNTHESIS OF OPTICALLY PURE (S) - 3-CYANO-5-METHYL-HEXANOIC ACID ALKYL ESTER, AN INTERMEDIATE OF (S)- PREGABALIN

The present invention is directed towards synthesis of (S) - 3-cyano-5-methyl-hexanoic acid ethyl ester. A cost effective, eco-friendly process for preparation of enantiomerically pure (S)-3-cyano-5-methyl-hexanoic acid alkyl ester, intermediate of γ-amino acids, particularly (S)-pregabalin.

Esterification of dicarboxylic acids with benzyl alcohol under the action of the microwave radiation

Reaction of dicarboxylic acid with benzyl alcohol under the microwave irradiation proceeds faster as compared to the thermal conditions. The main reaction products are alkyl dicarboxylates, and the monoester and dibenzyl ether are formed as the side products. A proposal about the nature of the nonthermal effect in the reactions stimulated by the microwave irradiation is considered.

Oxidative coupling of carbonyl compounds by using pentavalent biphenyl-2,2′-ylenebismuth reagents

p-Tolylbiphenyl-2,2′-ylenebismuth bis(trifluoromethanesulfonate) reacted with lithium enolates derived from ketones, carboxylic esters, and thioesters to afford the corresponding oxidative coupling products in good to high yields. Copyright

SELECTIVE MONOETHERIFICATION AND MONOESTERIFICATION OF DIOLS AND DIACIDS UNDER PHASE-TRANSFER CONDITIONS

Research on the selectivity of etherification reactions of diols and esterification reactions of diacids by alkyl halides under phase-transfer catalysis has shown that under such conditions, selectivity of monoetherification increases in the order prim sec tert diols, though overall yield of monoether decreases from sec to tert diols.Monoesterification of diacids was accomplished with a high degree of selectivity.Optimal extraction of diols and diacids was found to correspond in general to chain lengths of around 5 carbons.This could mean that the complex formed between the catalyst and the anion to react is stabilized for certain carbon lengths by inner solvation in virtue of its spatial conformation.