2-(3,4-Difluoro-2-methoxyphenyl)acetic acid
[CAS# 1558274-26-2]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives
• Name: 2-(3,4-Difluoro-2-methoxyphenyl)acetic acid
• Synonyms: (3,4-Difluoro-2-methoxyphenyl)acetic acid
• Molecular Formula: C₉H₈F₂O₃
• Molecular Weight: 202.15
• CAS Registry Number: 1558274-26-2
• SMILES: COC1=C(C=CC(=C1F)F)CC(=O)O

Properties

• Density: 1.4±0.1 g/cm³ Calc.^*
• Boiling point: 286.5±35.0 ºC 760 mmHg (Calc.)^*
• Flash point: 127.1±25.9 ºC (Calc.)^*
• Index of refraction: 1.502 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Discovory and Applicatios

2-(3,4-Difluoro-2-methoxyphenyl)acetic acid is an aromatic carboxylic acid derivative characterized by a phenylacetic acid core substituted with two fluorine atoms at the 3 and 4 positions and a methoxy group at the 2 position on the aromatic ring. Its molecular formula is C₉H₈F₂O₃, and the structure features both electron-donating and electron-withdrawing substituents that significantly influence its reactivity and physicochemical properties.

This compound can be synthesized by various established routes, including the alkylation of substituted phenols followed by carboxymethylation. One common approach involves starting from 3,4-difluoro-2-methoxybenzene, which undergoes side-chain bromination to introduce a benzylic halide, followed by nucleophilic substitution with a cyanide ion to form a nitrile intermediate. Hydrolysis of the nitrile under acidic or basic conditions then yields the corresponding acetic acid derivative.

The presence of the 3,4-difluoro substitution pattern enhances the electron-withdrawing character of the aromatic ring, increasing the acidity of the carboxylic acid group compared to unsubstituted phenylacetic acid. The methoxy group at the ortho position contributes electron density via resonance, partially offsetting the effects of the fluorine atoms and influencing both the molecule’s conformation and reactivity.

2-(3,4-Difluoro-2-methoxyphenyl)acetic acid has potential utility in the pharmaceutical and agrochemical industries as a building block for the synthesis of more complex biologically active molecules. Substituted phenylacetic acid derivatives are frequently encountered in drug discovery due to their structural resemblance to natural products and their ability to act as enzyme inhibitors or receptor ligands. The difluorinated and methoxylated motif can modulate lipophilicity, metabolic stability, and binding affinity, which are critical parameters in medicinal chemistry.

In addition to pharmaceutical applications, such compounds may also be used in the development of specialty chemicals, dyes, or advanced materials where specific substitution patterns are required for tuning electronic or photophysical properties.

Physically, 2-(3,4-difluoro-2-methoxyphenyl)acetic acid is expected to be a crystalline solid under ambient conditions, with moderate solubility in organic solvents such as ethanol, methanol, and dimethyl sulfoxide. Its melting point and spectral properties (including NMR and IR) are consistent with other difluorinated phenylacetic acid analogues, showing characteristic shifts due to the electron-withdrawing fluorine atoms and electron-donating methoxy group.

Chemically, it is stable under standard storage conditions but may undergo decarboxylation at elevated temperatures or react with nucleophiles under strong basic conditions. The functional groups present make it amenable to further derivatization, such as esterification, amidation, or halogenation, allowing incorporation into a variety of synthetic schemes.

In summary, 2-(3,4-difluoro-2-methoxyphenyl)acetic acid is a structurally distinct aromatic acid with dual electron-withdrawing and donating substituents. Its unique substitution pattern imparts useful chemical and physical properties, making it an important intermediate for the synthesis of advanced organic compounds in pharmaceutical and materials research.