766-39-2

Usage

Uses

Used in Chemical Synthesis:
2,3-Dimethylmaleic anhydride is used as a key intermediate in the synthesis of maleimides, which are important compounds in various chemical reactions and applications.
Used as Amino Group Protecting Agent:
In the field of biochemistry, 2,3-Dimethylmaleic anhydride serves as an amino group protecting agent for superoxide dismutase, an enzyme that plays a crucial role in protecting cells from oxidative damage.
Used in Pharmaceutical Industry:
2,3-Dimethylmaleic anhydride is used in the preparation of dimethylmaleic acid dimethyl ester, which has potential applications in the pharmaceutical industry for the development of new drugs.
Used in Protein Research:
It also serves as a reactant in the dissociation of ribosomal proteins, which is an essential process in understanding protein structure and function.
Used in Insect Control:
The isolated molecule 2,3-Dimethylmaleic anhydride has shown potent insecticidal activity in fumigation bioassay against several insect species, such as houseflies, cockroaches, and stored-product insects. This makes it a potential candidate for use in the agricultural and pest control industries.
Used in Nanoparticle Development:
2,3-Dimethylmaleic anhydride has been used as a linker to a cell-penetrating peptide-based nanoparticle, which can enhance the delivery of therapeutic agents in the field of nanotechnology and drug delivery systems.

Safety Profile

Questionable carcinogen with experimental tumorigenic data. When heated to decomposition it emits acrid smoke and irritating fumes. See also ANHYDRIDES.

Purification Methods

Distil the anhydride from *benzene/ligroin and sublime in a vacuum. [Beilstein 17/11 V 69.]

InChI:InChI=1/C6H6O3/c1-3-4(2)6(8)9-5(3)7/h1-2H3

Upstream product

• 123-91-1 1,4-dioxane 
• 488-21-1 2,3-dimethylmaleic acid 
• 71-43-2 benzene 
• 89533-85-7 α-methyl-γ-butyrolactone-β-carboxylic acid 
• 60-29-7 diethyl ether 
• 64-17-5 ethanol 
• 35612-17-0 dimethyl (E)-2,3-dimethyl-2-butenedioate 
• 75-99-0 2,2-Dichloropropionic acid 
• 64711-98-4 dimethylmaleic acid ; disilver (I)-compound 
• 110-15-6 succinic acid 
• 108-24-7 acetic anhydride 
• 127-17-3 2-oxo-propionic acid 
• 150-90-3 sodium succinate 
• 21788-49-8 (E)-2,3-dimethyl-2-butenedioic acid 

Downstream Products

• 63944-99-0 1-(4-amino-phenyl)-3,4-dimethyl-pyrrole-2,5-dione 
• 78271-86-0 4-oxo-2.3-dimethyl-4-phenyl-cis-crotonic acid 
• 63751-07-5 1-amino-3,4-dimethyl-pyrrole-2,5-dione 
• 5754-17-6 4,5-dimethyl-1,2-dihydro-pyridazine-3,6-dione 
• 608-40-2 rac-2,3-dimethylsuccinic acid 
• 91392-45-9 3,4-dimethyl-1-(phenylamino)-1H-pyrrole-2,5-dione 
• 54845-45-3 2,3-dichloro-2,3-dimethyl-succinic acid-anhydride 
• 71190-96-0 5-Hydroxy-3,4-dimethyl-5-undecyl-5H-furan-2-one 
• 6066-51-9 5-Aethyl-5-hydroxy-3,4-dimethyl-5H-furan-2-on 
• 6066-55-3 5-Heptyl-5-hydroxy-3,4-dimethyl-5H-furan-2-on 
• 124097-54-7 hydroxydihydrobovolide 
• 6066-54-2 5-Hexyl-5-hydroxy-3,4-dimethyl-5H-furan-2-on 
• 6066-56-4 5-Octyl-5-hydroxy-3,4-dimethyl-5H-furan-2-on 
• 71190-95-9 5-Decyl-5-hydroxy-3,4-dimethyl-5H-furan-2-one 

Relevant academic research and scientific papers

A regioselective tsuji-trost pentadienylation of 3-allyltetronic acid

A regioselective Tsuji-Trost reaction of sodium 3-allyltetronate with methyl 5-trimethylsilylpenta-2,4-dienyl carbonate was developed. Carbon-carbon bond formation at the more highly substituted terminus of the pentadienyl residue was possible by introduc

Synthesis and pH-dependent hydrolysis profiles of mono- and dialkyl substituted maleamic acids

Maleamic acid derivatives as weakly acid-sensitive linkers or caging groups have been used widely in smart delivery systems. Here we report on the controlled synthetic methods to mono- and dialkyl substituted maleamic acids and their pH-dependent hydrolysis behaviors. Firstly, we studied the reaction between n-butylamine and citraconic anhydride, and found that the ratio of the two n-butyl citraconamic acid isomers (α and β) could be finely tuned by controlling the reaction temperature and time. Secondly, we investigated the effects of solvent, basic catalyst, and temperature on the reaction of n-butylamine with 2,3-dimethylmaleic anhydride, and optimized the reaction conditions to efficiently synthesize the dimethylmaleamic acids. Finally, we compared the pH-dependent hydrolysis profiles of four OEG-NH2 derived water-soluble maleamic acid derivatives. The results reveal that the number, structure, and position of the substituents on the cis-double bond exhibit a significant effect on the pH-related hydrolysis kinetics and selectivity of the maleamic acid derivatives. Interestingly, for the mono-substituted citraconamic acids (α-/β-isomer), we found that their hydrolyses are accompanied by the isomerization between the two isomers.

Preparation method of 2-methyl-3-ethyl maleic amide

The invention relates to a preparation method of 2-methyl-3-ethyl maleic amide. The method comprises the following steps: preparing dimethyl maleic anhydride; preparing 2-methyl-3-ethyl maleic anhydride; and preparing 2-methyl-3-ethyl maleic amide. A process route develops a synthetic method of a series of maleimide and maleic anhydride, and meanwhile, a flavoring application experiment is performed on the series of precursor-aroma compounds, thereby providing an important support for developing novel perfume materials.

Preparation of the maleic anhydride nucleus from dichloro γ-lactams: Focus on the role of the N-substituent in the functional rearrangement and in the hydrolytic steps

The preparation of the 3,4-dialkyl-substituted maleic anhydride nucleus, through the functional rearrangement of dichloro γ-lactams, allowed the comparison of various N-substituents in the functional rearrangement step. The 2-pyridyl group proved to be the most appropriate N-substituent for the hydrolysis of the 5-methoxy-1,5-dihydro-2H-pyrrol-2-one intermediate into the 5-hydroxy adduct, and for the hydrolysis of the maleimide nucleus into the maleic anhydride. The oxidation of the 5-hydroxy-1,5-dihydro-2H-pyrrol-2-one into the corresponding maleimide was achieved with manganese(IV) oxide. Georg Thieme Verlag Stuttgart.

A short approach to chaetomellic anhydride A from 2,2-dichloropalmitic acid: Elucidation of the mechanism governing the functional rearrangement of the chlorinated pyrrolidin-2-one intermediate

Chaetomellic anhydride A was efficiently attained in three steps, starting from 2,2-dichloropalmitic acid and 2-(3-chloro-2-propenylamino)pyridine. Atom transfer radical cyclisation selectively formed the cis-stereoisomer of the trichloropyrrolidin-2-one, which underwent a stereospecific functional rearrangement to form a substituted maleimide. The choice of 2-pyridyl, as 'cyclisation auxiliary' in the atom transfer radical cyclisation step, proved beneficial for hydrolysis of the maleimide to form the desired anhydride.

An efficient synthesis of dimethylmaleic anhydride

A facile three-step synthesis of dimethylmaleic anhydride (8) with 74% overall yield has been described starting from maleimide 1, via methylmaleimide 4, using two Wittig reactions followed by an alkaline hydrolysis.

Vapor-phase oxidation and oxidative ammonolysis of some methyl derivatives of biphenyl

Main pathways arc established of catalytic oxidative transformations of 3,4-di- and 3,3',4,4'-tetramethylbiphenyls in vapor phase. The possibility is analyzed of obtaining the corresponding anhydrides, imides, and nitriles of biphenylcarboxylic acids in yields of up to 59-69%.

Dicarboxylic Acids Link Proton Transfer Across a Liquid Membrane to the Synthesis of Acyl Phosphates. A Model for P-Type H(+)-ATPases

H(+)-ATPases are ion pumps that link proton transfer across cell membranes to the synthesis or hydrolysis of ATP.A current research goal is to understand the molecular-level mechanism of this linking.We present a chemical model that mimics some features of H(+)-ATPases by linking proton transfer across a liquid membrane to the synthesis of acyl phosphates using carboxylic acid anhydride intermediates.Citraconic acid (cis-2-methyl-2-butenedioic acid) accelerated the transfer of protons from a pH 0.3 solution across a chloroform liquid membrane to a pH 10 solution.The mechanism involved spontaneous formation of a small amount of citraconic anhydride (0.6percent) in the pH 0.3 layer.This anhydride partitioned into the chloroform layer and diffused to the pH 10 layer, where it hydrolyzed, generating two protons.When the pH 10 layer contained phosphate (1.0 M), some of the citraconic anhydride reacted with phosphate to form citraconyl phosphate, 5.0percent yield.In separate experiments, we confirmed that citraconyl phosphate had high phosphoryl donor potential by reacting it with morpholine to form a phosphoramidate (11.5percent yield) or with fluoride to form fluorophosphonate (32percent yield).To demonstrate the link between an acyl phosphate and a proton gradient in the reverse direction, we used succinyl phosphate, whose hydrolysis occurs in two steps: formation of succinic anhydride, which consumes protons, followed by hydrolysis of succinic anhydride, which releases protons.We generated a pH gradient by carrying out these two steps in separate solutions.Hydrolysis of succinyl phosphate (3.9 mmol) at pH 6.00 started with a increase in pH to 6.16 (0.59 mmol of H(+) consumed) caused by the formation of succinic anhydride.We extracted this anhydride with dichloromethane and transferred it to a separate solution at pH 6.05.Hydrolysis of the anhydride released protons (0.36 mmol), decreasing the pH to 5.23.Our model suggests that H(+)-ATPases could use acyl phosphates and carboxylic acid anhydride intermediates to link proton transfer to ATP synthesis or hydrolysis.

Process for the preparation of dimethylmaleic anhydride

The reaction of maleic acid, fumaric acid and/or maleic anhydride at elevated temperature and in the presence of catalytic amounts of a heterocyclic amidine or a salt thereof with protonic acids affords dimethylmaleic anhydride in good yield.

Process for the preparation of dimethylmaleic anhydride

The reaction of maleic acid, fumaric acid and/or maleic anhydride in the presence of N-acylated heterocyclic amidines and at elevated temperature affords dimethylmaleic anhydride in good yield. Catalytic amounts of the amidine employed are sufficient for said reaction.