This article was accepted into the corpus but its outbound wikilinks were never NER-processed — typical at the deepest BFS hop or when the run's entity cap was reached. No expansion funnel to show.
| Malonic acid | |
|---|---|
| Name | Malonic acid |
| IUPAC name | Propane-1,3-dioic acid |
| Other names | Malonic acid; 1,3-propanedioic acid |
| Formula | C3H4O4 |
| Molar mass | 104.06 g·mol−1 |
| Density | 1.59 g·cm−3 (solid) |
| Melting point | 135–137 °C |
| Boiling point | Decomposes |
| Solubility | Soluble in water, ethanol |
Malonic acid is a simple dicarboxylic acid used extensively in organic synthesis, industrial chemistry, and biochemical studies. It is a crystalline solid with two carboxyl groups that confer acidity and reactivity useful in condensation, alkylation, and decarboxylation reactions. Prominent in classical named reactions and modern synthetic routes, malonic acid connects to a wide range of compounds, reagents, catalytic methods, and industrial processes.
Malonic acid has the formula C3H4O4 and exists as a diprotic acid with pKa1 ≈ 2.83 and pKa2 ≈ 5.69, reflecting sequential deprotonation similar to other dicarboxylic acids such as Oxalic acid, Succinic acid, Glutaric acid, Adipic acid, Terephthalic acid, Phthalic acid, Maleic acid, and Fumaric acid. Its central methylene group is activated by the adjacent carbonyls, enabling enolization and resonance-stabilized carbanions analogous to stabilization in Acetoacetic ester and Malonate ester systems. Crystal structure analyses, including work referenced by laboratories at Harvard University, Massachusetts Institute of Technology, University of Cambridge, University of Oxford, and Stanford University, show hydrogen-bonded networks comparable to those seen in Benzoic acid polymorph studies. Physical properties such as melting point and solubility are tabulated in compilations produced by organizations like National Institute of Standards and Technology and referenced in handbooks from American Chemical Society publications.
Historically, malonic acid was prepared by hydrolysis of malononitrile or by oxidation of glycerol derivatives in methods developed during the industrialization periods associated with companies such as DuPont and BASF. Contemporary production routes include hydrolysis of diesters produced by esterification processes described in patent literature from firms including Dow Chemical Company and Shell plc, as well as catalytic oxidation methods pursued at research centers like Max Planck Society institutes and industrial chemistry groups at Imperial College London. Academic syntheses reported by groups at University of California, Berkeley, ETH Zurich, University of Tokyo, Seoul National University, and Peking University explore green chemistry approaches using catalysts developed by teams led by awardees of Nobel Prize in Chemistry-related work such as methodologies inspired by principles from Paul Sabatier, Ernest Rutherford-era catalysis histories, and modern flow chemistry systems championed by laboratories at MIT and University of Groningen.
Malonic acid and its esters participate in the malonic ester synthesis, a cornerstone reaction that yields substituted acetic acids via alkylation and decarboxylation, closely related to classic transformations like the Claisen condensation, Knoevenagel condensation, and Perkin reaction. Alkylation of malonate anions uses bases and alkyl halides as studied in the context of nucleophilic substitution mechanisms investigated at institutions including Caltech and Columbia University. Decarboxylation pathways connect to cleavage reactions examined by researchers at University of Chicago and Yale University; derivatives such as malonates are precursors to pharmaceuticals developed by companies like Pfizer, Roche, GlaxoSmithKline, AstraZeneca, and Novartis. Malonic acid also forms active methylene compounds used in syntheses of heterocycles found in natural products isolated by teams at Smithsonian Institution and Scripps Research. Named reactions and reagents related to malonic acid include the Diethyl malonate alkylation, applications in Suzuki reaction-type cross-couplings after functionalization, and use in protocols optimized at Lawrence Berkeley National Laboratory.
While malonic acid is not a standard intermediate of central metabolism like compounds cataloged in Krebs cycle descriptions at Max Planck Institute for Biochemistry or referenced in textbooks from Cold Spring Harbor Laboratory, malonate (the anion) is a competitive inhibitor of succinate dehydrogenase—a component of respiratory chain complexes studied by researchers at NIH and Howard Hughes Medical Institute. This inhibition links malonate to experimental models of mitochondrial dysfunction employed by groups at Johns Hopkins University and Mayo Clinic. In microbial metabolism, pathways for degradation and assimilation of dicarboxylic acids are researched in laboratories at Wageningen University and University of Wisconsin–Madison, where malonate-related enzymes and transporters are characterized. Studies in plant physiology at INRAE and University of Wageningen examine exudation and soil interactions of small dicarboxylates, and clinical investigations by teams at Cleveland Clinic and Karolinska Institutet explore metabolic effects and potential toxicities.
Malonic acid and malonates serve as building blocks in the manufacture of agrochemicals, pharmaceuticals, fragrances, and polymers; companies such as Bayer, Syngenta, BASF, Dow Chemical Company, and Monsanto have used malonate chemistry in product pipelines. It is a key intermediate in the synthesis of barbiturates historically linked to research at Rochester Institute of Technology and drug discovery programs at Eli Lilly and Company. Malonic derivatives are employed in medicinal chemistry campaigns at Merck & Co., Johnson & Johnson, and Boehringer Ingelheim and in ligand design for asymmetric catalysis developed by groups awarded the Nobel Prize in Chemistry for organocatalysis and asymmetric hydrogenation work. In materials science, malonates are precursors to chelating agents and coordination complexes explored by teams at Argonne National Laboratory and Los Alamos National Laboratory for applications in catalysis and energy storage. Analytical standards for chromatography and spectroscopy are supplied by firms like Sigma-Aldrich.
Material safety data and regulatory guidance from agencies such as Occupational Safety and Health Administration, European Chemicals Agency, Environmental Protection Agency, and World Health Organization classify malonic acid with considerations for skin and eye irritation and environmental release. Standard industrial controls recommended by groups like American National Standards Institute and Institute of Chemical Engineers include ventilation, personal protective equipment, and waste management consistent with protocols at industrial sites such as Shell plc refineries and research laboratories at Lawrence Livermore National Laboratory. Toxicological studies reported in journals associated with American Association for the Advancement of Science and clinical reports from Centers for Disease Control and Prevention inform exposure limits and first-aid measures.
Category:Carboxylic acids