2-((2,6-Difluorophenyl)amino)-2-oxoacetic acid
[CAS# 1018295-42-5]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Carboxylic acid
• Name: 2-((2,6-Difluorophenyl)amino)-2-oxoacetic acid
• Molecular Formula: C₈H₅F₂NO₃
• Molecular Weight: 201.13
• CAS Registry Number: 1018295-42-5
• EC Number: 826-296-9
• SMILES: C1=CC(=C(C(=C1)F)NC(=O)C(=O)O)F

Properties

• Density: 1.6±0.0 g/cm³, Calc.^*
• Index of Refraction: 1.585, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07;GHS08;GHS09 Danger
• Risk Statements: H302-H319-H372-H410
• Safety Statements: P260-P264-P273-P301+P312-P305+P351+P338-P314

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2A	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335

• Transport Information: UN 3077

Discovery and Applications

2-((2,6-Difluorophenyl)amino)-2-oxoacetic acid is a synthetic compound characterized by its difluorophenyl group, amino functionality, and ketoacetic acid moiety. This combination of functional groups imparts unique physicochemical and biological properties, making it a valuable molecule in pharmaceutical research and organic synthesis. The discovery of this compound stems from efforts to develop versatile intermediates for advanced chemical transformations and bioactive molecules.

The synthesis of 2-((2,6-difluorophenyl)amino)-2-oxoacetic acid typically involves the reaction of 2,6-difluoroaniline with an appropriate acylation reagent, such as oxalyl chloride or a similar keto compound. The reaction is often catalyzed by a base and performed under controlled conditions to ensure selective formation of the desired product. This method yields a highly reactive compound suitable for further chemical modifications.

In pharmaceutical research, 2-((2,6-difluorophenyl)amino)-2-oxoacetic acid has been investigated as a structural scaffold for designing enzyme inhibitors and receptor modulators. The presence of the difluorophenyl group enhances lipophilicity and bioavailability, while the amino and ketoacetic acid functionalities enable interactions with biological targets through hydrogen bonding and chelation. These features make it a promising candidate for developing drugs aimed at treating inflammatory diseases, cancer, and metabolic disorders.

Additionally, the compound serves as a precursor in organic synthesis, particularly for constructing heterocyclic frameworks. The ketoacetic acid moiety is reactive in cyclization reactions, facilitating the formation of various nitrogen-containing heterocycles. This utility has expanded its applications in material science, where such heterocycles are used in optoelectronic devices and other advanced materials.

Future research continues to explore the optimization of synthetic routes for 2-((2,6-difluorophenyl)amino)-2-oxoacetic acid and its derivatives, aiming to improve yield and sustainability. Furthermore, ongoing studies on its biological properties seek to unlock its full potential as a building block for next-generation therapeutics and functional materials.

References

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