2-(3-Methoxyphenyl)succinic Acid: Properties & Applications
2-(3-Methoxyphenyl)succinic Acid: Properties & Applications
2-(3-Methoxyphenyl)succinic acid is an aryl-substituted dicarboxylic acid derivative bearing a meta-methoxy substituent on the phenyl ring, making it a structurally versatile building block relevant to organic synthesis and the preparation of pharmaceutical intermediates.
- Chemical Name
- 2-(3-Methoxyphenyl)succinic acid
- SKU
- S771025
- Molecular Formula
- C₁₁H₁₂O₅
- Molecular Weight
- 224.21 g/mol
- Functional Groups
- Two carboxylic acid groups (diacid) and one methoxy group
- Chiral Center
- One stereocenter at C-2 (alpha carbon bearing the aryl group)
- Supplier Reference
- Also listed as McLean M764710
Chemical Structure and Physical Properties
2-(3-Methoxyphenyl)succinic acid (molecular formula C₁₁H₁₂O₅, MW 224.21 g/mol) is a substituted succinic acid in which a 3-methoxyphenyl (meta-anisyl) group is attached to the alpha carbon of the succinic acid backbone. The compound contains two free carboxylic acid moieties, rendering it a bifunctional diacid with pKa values expected to be in the range typical of aryl-substituted succinic acids. The presence of an electron-donating methoxy group at the meta position of the aromatic ring influences the electronic distribution of the molecule without introducing significant steric bulk adjacent to the reaction centers.
The compound possesses one stereocenter at C-2, meaning it can exist as (R)- and (S)-enantiomers as well as a racemic mixture. Researchers should verify the stereochemical specification of the supplied material (racemic or enantiopure) for applications sensitive to chirality. The solid is expected to be a white to off-white crystalline powder at room temperature, though specific melting point and solubility data should be confirmed from the certificate of analysis (CoA) provided with each lot.
Synthesis and Preparation Routes
Aryl-substituted succinic acids such as 2-(3-Methoxyphenyl)succinic acid are commonly prepared via several established synthetic strategies. One classical approach involves the malonic ester synthesis, in which a 3-methoxybenzyl halide or equivalent electrophile is alkylated onto a malonate ester, followed by hydrolysis and decarboxylation to yield the monoaryl succinic acid. Alternatively, Michael addition of a suitable nucleophile to methylene-maleic or fumaric acid derivatives followed by appropriate functional group manipulation can provide access to the target diacid.
Enzymatic or asymmetric catalytic methods have been reported for related aryl succinic acid frameworks to provide enantiomerically enriched products, which is particularly relevant for pharmaceutical applications where stereochemistry is critical. The specific synthesis route and resultant enantiomeric excess of the Aladdin Scientific material (S771025) should be confirmed with the technical data sheet or by contacting our technical support team.
Research and Industrial Applications
2-(3-Methoxyphenyl)succinic acid serves primarily as a synthetic building block and intermediate in medicinal chemistry and fine chemical synthesis. Diaryl- and aryl-succinic acid motifs are well-represented in bioactive molecules and pharmaceutical candidates, with succinic acid scaffolds appearing in enzyme inhibitors, receptor ligands, and other pharmacophores. The meta-methoxy substitution pattern is of particular interest in drug discovery as it modulates lipophilicity, membrane permeability, and target binding relative to unsubstituted or ortho/para-substituted analogs.
Beyond pharmaceutical applications, aryl succinic acid derivatives may find use in the synthesis of specialty polymers, surfactants, and chiral auxiliaries. As a bifunctional diacid, it can participate in condensation polymerization reactions or be converted to anhydrides, esters, amides, and other activated derivatives for further functionalization. Researchers in total synthesis may also employ it as a chiral or prochiral precursor toward more complex natural product analogs.
Handling, Storage, and Safety Considerations
As with most carboxylic acid-containing compounds, 2-(3-Methoxyphenyl)succinic acid should be handled with standard laboratory precautions. Personnel should wear appropriate personal protective equipment (PPE) including nitrile gloves, safety glasses, and a laboratory coat when handling the material. Avoid inhalation of dust or aerosols generated during weighing operations; use a fume hood or appropriate dust control measures when processing powdered material.
The compound should be stored in a tightly sealed container in a cool, dry location, away from strong bases, oxidizing agents, and reactive amines. Standard storage at room temperature under dry conditions is generally appropriate for solid aryl carboxylic acids, but researchers should consult the product-specific CoA and SDS (Safety Data Sheet) provided by Aladdin Scientific for authoritative storage temperature recommendations and hazard classifications. Disposal should comply with applicable local and institutional regulations for organic chemical waste.
Frequently asked questions
What is the molecular weight of 2-(3-Methoxyphenyl)succinic acid?
The molecular weight of 2-(3-Methoxyphenyl)succinic acid is 224.21 g/mol, corresponding to the molecular formula C₁₁H₁₂O₅. This should be confirmed against the certificate of analysis supplied with each specific lot.
Is 2-(3-Methoxyphenyl)succinic acid available as an enantiopure compound?
The compound contains one stereocenter and can exist as (R)-, (S)-, or racemic forms. Customers interested in a specific enantiomer should contact Aladdin Scientific technical support or consult the product listing for available stereochemical specifications of SKU S771025.
What solvents are suitable for dissolving 2-(3-Methoxyphenyl)succinic acid?
Aryl succinic acid derivatives are generally soluble in polar organic solvents such as methanol, ethanol, ethyl acetate, and dimethyl sulfoxide (DMSO), and may show limited solubility in water and non-polar solvents. Specific solubility data for this compound should be verified experimentally or confirmed via the product SDS and CoA from Aladdin Scientific.
What are the main applications of 2-(3-Methoxyphenyl)succinic acid in research?
This compound is primarily used as a building block in medicinal chemistry and organic synthesis, including the preparation of pharmaceutical intermediates, chiral precursors, specialty esters and amides, and potentially as a monomer in condensation polymer research. Its aryl succinic acid scaffold is relevant to the synthesis of bioactive molecules and enzyme inhibitor frameworks.
How should 2-(3-Methoxyphenyl)succinic acid be stored?
Store the compound in a tightly sealed container in a cool, dry place, away from strong bases and oxidizing agents. Consult the Aladdin Scientific SDS and CoA for lot-specific storage temperature recommendations and full hazard information.
References
- Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry, 2nd ed.; Oxford University Press: Oxford, 2012. (General reference for carboxylic acid chemistry and malonic ester synthesis)
- March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 4th ed.; Wiley-Interscience: New York, 1992. (Reference for aryl substituted succinic acid synthesis strategies)
- Aladdin Scientific product page for 2-(3-Methoxyphenyl)succinic acid, SKU S771025. Certificate of Analysis and Safety Data Sheet available upon request.
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
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