[3-(Trifluoromethyl)phenyl]malonic acid
[CAS# 144758-28-1]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Carboxylic acid
• Name: [3-(Trifluoromethyl)phenyl]malonic acid
• Molecular Formula: C₁₀H₇F₃O₄
• Molecular Weight: 248.16
• CAS Registry Number: 144758-28-1
• SMILES: C1=CC(=CC(=C1)C(F)(F)F)C(C(=O)O)C(=O)O

Properties

• Density: 1.5±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.510, Calc.^*
• Boiling Point: 339.9±42.0 ºC (760 mmHg), Calc.^*
• Flash Point: 159.4±27.9 ºC, Calc.^*

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

Discovory and Applicatios

[3-(Trifluoromethyl)phenyl]malonic acid, with the chemical formula C₁₀H₇F₃O₄, is a unique compound characterized by a trifluoromethylphenyl group attached to the malonic acid backbone. This chemical structure gives it unique properties that can be applied in various fields of chemistry and industry.

The synthesis and discovery of [3-(trifluoromethyl)phenyl]malonic acid originated from the desire to incorporate fluorinated aromatic groups into organic molecules. Researchers have tried to use the unique electronic and steric effects of the trifluoromethyl group to enhance the reactivity and functionality of the compound. The synthesis of this compound usually involves the reaction of malonic acid derivatives with trifluoromethylphenyl-containing precursors under controlled conditions to achieve the desired substitution pattern, which can be synthesized through a multi-step synthetic route. A common method is the reaction of malonic acid with an aldehyde or ketone containing a trifluoromethylphenyl group to form an intermediate. Heating or acidic conditions then promote the decarboxylation of the intermediate to obtain [3-(trifluoromethyl)phenyl]malonic acid.

[3-(Trifluoromethyl)phenyl]malonic acid is an important building block in organic synthesis. Its trifluoromethylphenyl group enhances the reactivity of the compound and modifies its chemical properties, making it suitable for the synthesis of complex molecules, including pharmaceuticals, agrochemicals, and specialty chemicals.

In medicinal chemistry, [3-(trifluoromethyl)phenyl]malonic acid derivatives are used as intermediates in the synthesis of bioactive compounds and drug candidates. The trifluoromethyl group can modulate the biological activity, pharmacokinetics, and metabolic stability of the compound, thereby improving the efficacy and selectivity of the drug.

Similar to pharmaceuticals, derivatives of [3-(trifluoromethyl)phenyl]malonic acid are also used in agrochemicals for the development of herbicides, fungicides, and insecticides. These compounds have insecticidal activity and can be tailored to target specific pests while minimizing environmental impact.

The unique properties of [3-(trifluoromethyl)phenyl]malonic acid and its derivatives make them valuable in materials science applications. They are used in the synthesis of functional materials such as liquid crystals, polymers, and dyes, where their electronic and structural contributions are advantageous.

Proper handling and safety precautions should be followed during the synthesis, handling, and application of [3-(trifluoromethyl)phenyl]malonic acid and its derivatives. Regulatory guidelines ensure their safe production, use, and disposal, minimizing risks to human health and the environment.