636-48-6

Basic information

• Product Name: 2-ETHYLSUCCINIC ACID
• Synonyms: 2-ETHYLSUCCINIC ACID;2-Ethylbutanedioic acid;ethyl succinic acid;AKOS MSC-0138
• CAS NO: 636-48-6
• Molecular Formula: C₆H₁₀O₄
• Molecular Weight: 146.14
• EINECS: 211-259-6
• Mol File: 636-48-6.mol

Chemical Properties

• Melting Point: 83.5-85 °C
• Boiling Point: 250.7°C at 760 mmHg
• Flash Point: 119.7°C
• Appearance: /
• Density: 1.246g/cm³
• Vapor Pressure: 0.00674mmHg at 25°C
• Refractive Index: 1.473
• PKA: pK1:4.08(0) (25°C)
• CAS DataBase Reference: 2-ETHYLSUCCINIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-ETHYLSUCCINIC ACID(636-48-6)
• EPA Substance Registry System: 2-ETHYLSUCCINIC ACID(636-48-6)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 636-48-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
2-Ethylsuccinic acid is used as a building block in the synthesis of pharmaceuticals, contributing to the development of new drugs and therapeutic agents. Its unique structure allows for the creation of complex molecules with specific biological activities.
Used in Polymer Production:
In the polymer industry, 2-ethylsuccinic acid serves as a key component in the production of polymers, enhancing their properties and expanding their applications in various fields.
Used as a Chiral Resolving Agent:
2-Ethylsuccinic acid is utilized as a chiral resolving agent, playing a crucial role in the separation of enantiomers, which is essential in the production of pure pharmaceutical compounds with desired chiral properties.
Used in the Preparation of Biologically Active Molecules:
This dicarboxylic acid is employed as a starting material for the preparation of biologically active molecules, which can have significant implications in medicine and biotechnology.
Used as a Corrosion Inhibitor:
2-Ethylsuccinic acid has been investigated for its potential use as a corrosion inhibitor, offering protection to materials in various industrial settings where corrosion is a concern.
Used in Biodegradable Polymers:
As a component in biodegradable polymers, 2-ethylsuccinic acid contributes to the development of environmentally friendly materials that can degrade over time, reducing the environmental impact of plastic waste.

InChI:InChI=1/C6H10O4/c1-2-4(6(9)10)3-5(7)8/h4H,2-3H2,1H3,(H,7,8)(H,9,10)

Upstream product

• 51251-11-7 diethyl ethylsuccinate 
• 5671-99-8 2-ethylidenesuccinic acid 
• 923-06-8 bromosuccinic acid 
• 925-90-6 ethylmagnesium bromide 
• 108712-21-6 10-undecenylmagnesium chloride 
• 14035-81-5 ethylsuccinic anhydride 
• 7732-18-5 water 
• 16496-51-8 (±)-4-ethyldihydro-2(3H)-furanone 
• 14668-68-9 3,5-diethyl-dihydro-furan-2-one 
• 5204-64-8 3-pentenoic acid 
• 201230-82-2 carbon monoxide 
• 6117-91-5 (E/Z)-2-buten-1-ol 
• 151-50-8 potassium cyanide 
• 100-39-0 benzyl bromide 

Downstream Products

• 15012-53-0 2-ethylnaphthazarin 
• 4074-24-2 (R)-2-Ethylbutannedioic acid 
• 14035-81-5 (S)-ethylsuccinic anhydride 
• 14035-95-1 (S)-dimethyl 2-ethylsuccinate 
• 14035-81-5 ethylsuccinic anhydride 

Relevant articles and documents

Direct and Selective Synthesis of Adipic and Other Dicarboxylic Acids by Palladium-Catalyzed Carbonylation of Allylic Alcohols

A general and direct synthesis of dicarboxylic acids including industrially important adipic acid by palladium-catalyzed dicarbonylation of allylic alcohol is reported. Specifically, the combination of PdCl2 and a bisphosphine ligand (HeMaRaphos) promotes two different carbonylation reactions with high activity and excellent selectivity.

Ni-Catalyzed Site-Selective Dicarboxylation of 1,3-Dienes with CO2

A site-selective catalytic incorporation of multiple CO2 molecules into 1,3-dienes en route to adipic acids is described. This protocol is characterized by its mild conditions, excellent chemo- and regioselectivity and ease of execution under CO2 (1 atm), including the use of bulk butadiene and/or isoprene feedstocks.

Synthesis of d-labeled and unlabeled ethyl succinic anhydrides and application to quantitative analysis of peptides by isotope differential mass spectrometry

Ethyl succinic anhydride and its d5-labeled version have been synthesized and applied to quantitative analysis of peptides in combination with MALDI or ESI mass spectrometry. These modifiers react with amino groups in the N-termini and lysine side chains in proteins, and therefore the combination of these modifiers was shown to be a useful tool for quantification of peptides and hence for proteomics research.

Palladium Complexes with Bulky Diphosphine Ligands as Highly Selective Catalysts for the Synthesis of (Bio-) Adipic Acid from Pentenoic Acid Mixtures.

A series of sterically bulky diphosphines have been prepared, including P2 = trans-1,2-bis[(di-tert-butylphosphino)methyl]cyclohexane (4), (2-methylenepropane-1,3-diyl)bis(di-tert-butylphosphine) (5), bis[(di-tert-butylphosphino)methyl]dimethylsilane (6), and cis- and trans-11,12-bis[(di-tert-butylphosphino)methyl]-9,10-dihydro-9,10-ethanoanthracene (10 and 11). The corresponding palladium complexes of these ligands, P2Pd(CF3CO2)2, have been synthesized and characterized. The solid-state structures of [Pd(4)(CF3CO2)2], [Pd(5)(CF3CO2)2], [Pd(6)(CF3CO2)2], and [Pd(11)(CF3CO2)2] were obtained by single-crystal X-ray diffraction and confirm the bidentate binding mode of the ligand and a square-planar coordination geometry with a minor distortion from the ideal. The diphosphines in combination with Pd(OAc)2 have been applied in the hydroxycarbonylation of a mixture of pentenoic acid isomers to produce adipic acid with high selectivity (in several cases >95%). The (regio)selectivity of the hydroxycarbonylation reaction is highly dependent on the P2 diphosphine ligand structure, particularly the steric bulk of the substituents on the diphosphine donor and the P-Pd-P bite angle in the complexes, with respectively tertiary alkyl phosphine substituents (tert-butyl, adamantyl) and a C4 backbone P-Pd-P bite angle >100° being the common features of highly adipic acid selective systems. It is suggested that the regioselectivity of hydroxycarbonylation becomes largely driven by the chelation of the carboxylic acid functionality of pentenoic acid substrates, when smaller size P substituents and/or when P2 ligands with smaller bite angles (100°) are applied.

Pentenoic acid hydroxycarbonylation method

The invention discloses pentenoic acid hydroxycarbonylation into adipic acid. More particularly, it concerns one pentenoic acid hydroxycarbonylation method involving reaction water and carbon monoxide, in the presence of a catalyst comprising at least rho

Synthesis of monosubstituted succinic acids from tert-butylsuccinate

We report the preparation and alkylation of the dianion of t-butylsuccinate. This alkylation reaction has proven to be a useful method for the preparation of monosubstituted succinic acids and anhydrides.

2-Benzyl-2-methylsuccinic acid as inhibitor for carboxypeptidase A. synthesis and evaluation

Recently, Asante-Appiah et al. (Asante-Appiah, E.; Seetharaman, J.; Sicheri, F.; Yang, D. S.-C.; Chan, W. W.-C. Biochemistry 1997, 36, 8710-8715) reported that 2-ethyl-2-methylsuccinic acid is a highly potent inhibitor for carboxypeptidase A (CPA), a prototypic zinc protease. The X-ray crystal structure of the complex of the enzyme formed with 2-ethyl-2-methylsuccinic acid revealed that at the active site of CPA there is present a small cavity which accommodates the methyl group of the inhibitor. These investigators postulated that incorporation of a methyl group at the α-position to the carboxylate of existing inhibitors of CPA would improve the inhibitory potency. We have synthesized racemic and optically active 2-benzyl-2-methylsuccinic acids and evaluated their inhibitory activities for CPA to find the K(i) values to be 0.28, 0.15, and 17μM for racemic form, (R)-, and (S)-enantiomer, respectively. Contrary to the expectation, the effect on the binding affinity by the incorporation of the methyl group is minimal. The validity of the proposition that the small cavity may be utilized for the improvement of the inhibitory potency appears questionable. Copyright (C) 1999 Elsevier Science Ltd.

"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 ω-Unsaturated Acids

A short, high-yield method for the synthesis of ω-unsaturated acids have been developed that precludes any double-bond migration or hydrogenation.Key is the coupling reaction between Grignards of ω-unsaturated alkyl halides and the bromomagnesium salt of ω-bromo fatty acids.The reaction has been successfully extended to ω-bromo nitriles.The use of ω-chloro acids or α-bromo acids gives lower yields of heterocoupling products and substantial homocoupling.A catalyst study shows Li2CuCl4 to yield the most heterocoupling of several catalysts tried for the chloro acids, and Ni(II) or Cu(I) are best for the α-bromo acids.

Microbiological transformation of terpenes. XIX. Pathway of degradation of 3 p menthene in a soil pseudomonad (PL strain)

The acidic metabolites such as 1 hydroxy 3 p menthen 7 oic acid and 1 hydroxy 3 p menthen 9 oic acid which accumulated during the fermentation of 3 p menthene are found to be incapable of supporting the growth or respiration of bacteria. On the other hand, α ethylsuccinic acid, an acidic metabolite, and 3 p menthen 1 ol, a neutral metabolite, are freely metabolized by 3 p menthene grown cells. From these data an attempt was made to establish an energy yielding pathway for 3 p menthene.