Methyl 2,3,4-trifluorobenzoate
[CAS# 773873-68-0]

Identification

• Classification: Chemical reagent >> Organic reagent >> Ester >> Acid ester compound
• Name: Methyl 2,3,4-trifluorobenzoate
• Molecular Formula: C₈H₅F₃O₂
• Molecular Weight: 190.12
• CAS Registry Number: 773873-68-0
• EC Number: 830-815-4
• SMILES: COC(=O)C1=C(C(=C(C=C1)F)F)F

Properties

• Density: 1.4±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.455, Calc.^*
• Boiling Point: 214.3±40.0 ºC (760 mmHg), Calc.^*
• Flash Point: 86.4±19.6 ºC, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H227-H302-H315-H319-H335
• Precautionary Statements: P210-P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P319-P321-P330-P332+P317-P337+P317-P362+P364-P370+P378-P403-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2A	H319
Acute toxicity	Acute Tox.	4	H302
Flammable liquids	Flam. Liq.	4	H227
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovory and Applicatios

Methyl 2,3,4-trifluorobenzoate is an organic compound that belongs to the class of benzoate esters, characterized by the presence of three fluorine atoms at the 2, 3, and 4 positions of the benzene ring, along with a methyl ester group at the carboxyl position. This structure imparts unique chemical properties to the compound, making it an important intermediate in various synthetic and industrial applications.

The discovery of Methyl 2,3,4-trifluorobenzoate can be traced back to the broader interest in fluorinated aromatic compounds. Fluorination, the process of introducing fluorine atoms into organic molecules, has been extensively studied due to the unique properties that fluorine imparts, such as increased stability, solubility, and lipophilicity. Aromatic fluorinated compounds, such as Methyl 2,3,4-trifluorobenzoate, are of particular interest because the presence of fluorine atoms can significantly alter the electronic properties of the molecule, enhancing its reactivity and making it useful in a variety of chemical reactions.

One of the key applications of Methyl 2,3,4-trifluorobenzoate lies in its role as an intermediate in the synthesis of pharmaceuticals and agrochemicals. The trifluoromethyl group (–CF3) is known for its ability to modulate the bioactivity of organic compounds, and its presence in Methyl 2,3,4-trifluorobenzoate makes this compound a valuable building block for drug design. Trifluoromethylated aromatic compounds are frequently incorporated into drug molecules to enhance metabolic stability and optimize the pharmacokinetics of the compound. Methyl 2,3,4-trifluorobenzoate can thus be used as a precursor in the synthesis of more complex molecules that exhibit improved efficacy and selectivity in the treatment of diseases such as cancer, bacterial infections, and neurological disorders.

Another important application of Methyl 2,3,4-trifluorobenzoate is in the field of materials science. The fluorine atoms in the molecule can impart specific electronic and physical properties to the compounds in which Methyl 2,3,4-trifluorobenzoate is used. This includes enhanced solubility in organic solvents and improved resistance to environmental degradation. These properties make the compound a useful intermediate in the preparation of advanced materials, such as polymers, liquid crystals, and electronic devices, where the stability and performance of the material are critical.

The compound's role in organic synthesis is also notable, as it can participate in various electrophilic aromatic substitution reactions, allowing it to be easily functionalized into a wide range of derivatives. The trifluoromethyl group is particularly reactive, enabling the creation of a broad spectrum of novel compounds with tailored properties. This has made Methyl 2,3,4-trifluorobenzoate a versatile reagent in the development of new chemical entities with specific applications in fine chemicals, agricultural chemicals, and other specialized industries.

In the context of agrochemicals, Methyl 2,3,4-trifluorobenzoate can be used as a starting material for the synthesis of herbicides and pesticides. The introduction of fluorine atoms into agrochemical molecules is a well-known strategy to enhance their potency and persistence, making fluorinated compounds particularly useful in crop protection. Methyl 2,3,4-trifluorobenzoate, with its trifluoromethylated benzene ring, is a valuable intermediate for the development of such chemicals, contributing to their improved activity against pests and plant diseases.

In addition to its pharmaceutical and industrial applications, Methyl 2,3,4-trifluorobenzoate may have potential uses in analytical chemistry. Its unique structure and fluorine content can be exploited in the design of sensors or diagnostic assays. For instance, fluorinated compounds can be used as markers in spectroscopic or chromatographic techniques, aiding in the detection and quantification of other substances in complex mixtures.

In conclusion, Methyl 2,3,4-trifluorobenzoate is a versatile and valuable compound with a wide range of applications across pharmaceuticals, materials science, agrochemicals, and analytical chemistry. The presence of the trifluoromethyl group and the methyl ester group provides unique chemical properties that make this compound an important intermediate in the synthesis of more complex molecules with enhanced stability, reactivity, and performance. As research into the chemistry of fluorinated compounds continues, Methyl 2,3,4-trifluorobenzoate is likely to play an increasingly significant role in the development of new technologies and products.