Cas no 7407-59-2 (2-methylbut-2-enedioic acid)

2-Methylbut-2-enedioic acid is an unsaturated dicarboxylic acid with the molecular formula C5H6O4. It exists as a white crystalline solid and is structurally related to maleic and fumaric acids. This compound is notable for its conjugated double bond and carboxyl groups, which make it a versatile intermediate in organic synthesis, particularly in the production of polymers, resins, and specialty chemicals. Its reactivity allows for applications in cross-linking reactions and as a precursor for fine chemicals. The compound's stability under controlled conditions and its bifunctional nature contribute to its utility in industrial and research settings. Proper handling and storage are recommended due to its potential irritant properties.
2-methylbut-2-enedioic acid structure
2-methylbut-2-enedioic acid structure
Product Name:2-methylbut-2-enedioic acid
CAS No:7407-59-2
MF:C5H6O4
MW:130.098742008209
MDL:MFCD00002653
CID:862406
PubChem ID:638129
Update Time:2025-06-15

2-methylbut-2-enedioic acid Chemical and Physical Properties

Names and Identifiers

    • citraconic acid
    • 2-methyl-2-butenedioic acid
    • 2-methylbut-2-enedioic acid
    • Kyselina mesakonovaMethylfumaric acid
    • FT-0628231
    • 7407-59-2
    • NS00082008
    • Citronic acid; Methylfumaric acid
    • AKOS033199661
    • SY051520
    • DTXSID20862046
    • MFCD00002653
    • FT-0623952
    • MDL: MFCD00002653
    • Inchi: 1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h2H,1H3,(H,6,7)(H,8,9)
    • InChI Key: HNEGQIOMVPPMNR-UHFFFAOYSA-N
    • SMILES: OC(C(=CC(=O)O)C)=O

Computed Properties

  • Exact Mass: 130.02658
  • Monoisotopic Mass: 130.027
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 9
  • Rotatable Bond Count: 2
  • Complexity: 168
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 1
  • Topological Polar Surface Area: 74.6A^2
  • XLogP3: -0.1

Experimental Properties

  • Density: 1.387
  • Boiling Point: 336.6°Cat760mmHg
  • Flash Point: 171.5°C
  • PSA: 74.6

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2-methylbut-2-enedioic acid Production Method

Production Method 1

Reaction Conditions
1.1 Reagents: Water
Reference
Synthesis and pH-dependent hydrolysis profiles of mono- and dialkyl substituted maleamic acids
Su, Shan; et al, Organic & Biomolecular Chemistry, 2017, 15(39), 8384-8392

Production Method 2

Reaction Conditions
1.1 Solvents: Dichloromethane ;  24 h, 30 °C
1.2 Reagents: Sodium bicarbonate Solvents: Water
2.1 Reagents: Water
Reference
Synthesis and pH-dependent hydrolysis profiles of mono- and dialkyl substituted maleamic acids
Su, Shan; et al, Organic & Biomolecular Chemistry, 2017, 15(39), 8384-8392

2-methylbut-2-enedioic acid Raw materials

2-methylbut-2-enedioic acid Preparation Products

Additional information on 2-methylbut-2-enedioic acid

Introduction to 2-methylbut-2-enedioic acid (CAS No. 7407-59-2)

2-methylbut-2-enedioic acid, also known as dimethyl fumaric acid, is a significant compound in the field of organic chemistry and pharmaceutical research. With the CAS number 7407-59-2, this dicarboxylic acid derivative has garnered attention due to its unique structural properties and potential applications in various scientific domains. The compound features a conjugated system with two carboxyl groups, making it a versatile intermediate in synthetic chemistry and a candidate for further functionalization.

The molecular structure of 2-methylbut-2-enedioic acid consists of a methyl-substituted butadiene backbone with carboxylate groups at both ends. This configuration imparts interesting reactivity, enabling its use in the synthesis of more complex molecules. The presence of double bonds and carboxyl functional groups allows for diverse chemical transformations, including esterification, amidation, and polymerization reactions. These characteristics make it a valuable building block in the development of novel materials and bioactive compounds.

In recent years, 2-methylbut-2-enedioic acid has been explored for its pharmacological potential. Research has indicated that derivatives of this compound may exhibit anti-inflammatory, antioxidant, and even anticancer properties. The conjugated diene system is known to interact with biological targets in unique ways, potentially leading to therapeutic effects. For instance, studies have suggested that certain fumaric acid derivatives can modulate enzyme activity and signal transduction pathways, which are critical in disease mechanisms.

The pharmaceutical industry has shown interest in 2-methylbut-2-enedioic acid due to its structural similarity to naturally occurring fumaric acid, which is already used in the treatment of psoriasis. While dimethyl fumaric acid itself is not yet approved for medical use, its derivatives are being investigated for various conditions. The ability to modify the molecule while retaining its core structure provides researchers with a flexible platform to develop targeted therapies. This adaptability is particularly valuable in drug discovery pipelines where structural optimization is key.

From a synthetic chemistry perspective, CAS No. 7407-59-2 represents an important intermediate for producing more complex organic molecules. Its reactivity allows chemists to introduce additional functional groups or alter the conjugation pattern, leading to novel compounds with tailored properties. This flexibility is crucial in industrial applications where specific chemical behaviors are required for material science or fine chemical production.

Recent advancements in green chemistry have also highlighted the importance of sustainable synthesis methods for compounds like 2-methylbut-2-enedioic acid. Researchers are exploring biocatalytic routes and renewable feedstocks to produce this compound more efficiently while minimizing environmental impact. Such efforts align with global trends toward sustainable manufacturing practices in the chemical industry.

The analytical characterization of dimethyl fumaric acid is another area where significant progress has been made. Modern spectroscopic techniques such as NMR spectroscopy, mass spectrometry, and X-ray crystallography provide detailed insights into its molecular structure and purity. These tools are essential for ensuring high-quality compounds for research and industrial applications, where even minor impurities can affect performance.

In conclusion, CAS No. 7407-59-2 corresponds to a compound with broad utility across multiple scientific disciplines. Its structural features enable diverse applications in pharmaceuticals, materials science, and synthetic chemistry. As research continues to uncover new possibilities for this molecule and its derivatives, its significance is likely to grow further. The ongoing exploration of its pharmacological properties and synthetic potential underscores its importance as a chemical entity worthy of continued study and development.

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