3-(Trifluoromethyl)benzoyl chloride
[CAS# 2251-65-2]

Identification

• Classification: Chemical reagent >> Organic reagent >> Acid halide
• Name: 3-(Trifluoromethyl)benzoyl chloride
• Molecular Formula: C₈H₄ClF₃O
• Molecular Weight: 208.57
• CAS Registry Number: 2251-65-2
• EC Number: 218-844-5
• SMILES: C1=CC(=CC(=C1)C(F)(F)F)C(=O)Cl

Properties

• Density: 1.383
• Boiling point: 184-186 °C (750 mmHg)
• Refractive index: 1.476-1.478
• Water solubility: decomposes

Safety Data

• Hazard Symbols: GHS05 Danger
• Risk Statements: H314
• Safety Statements: P260-P264-P280-P301+P330+P331-P302+P361+P354-P304+P340-P305+P354+P338-P316-P321-P363-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin corrosion	Skin Corr.	1B	H314
Substances or mixtures corrosive to metals	Met. Corr.	1	H290
Skin corrosion	Skin Corr.	1C	H314
Specific target organ toxicity - single exposure	STOT SE	3	H335
Serious eye damage	Eye Dam.	1	H318
Eye irritation	Eye Irrit.	2	H319

• Transport Information: UN 3265

Discovery and Applications

3-(Trifluoromethyl)benzoyl chloride, a derivative of benzoyl chloride, was first synthesized and characterized through organic chemistry research aimed at developing novel fluorinated compounds. The synthesis typically involves the chlorination of 3-(trifluoromethyl)benzoic acid, resulting in the formation of the desired compound. Its discovery marked a significant advancement in fluorine chemistry, offering chemists a versatile building block for creating fluorinated molecules with unique properties and diverse applications.

3-(Trifluoromethyl)benzoyl chloride serves as a valuable intermediate in the synthesis of pharmaceutical compounds. Its trifluoromethyl group imparts unique physicochemical properties, such as increased lipophilicity and metabolic stability, making it a desirable moiety for drug design. Chemical modifications of the benzoyl chloride group enable the creation of drug candidates with improved pharmacokinetic profiles, target selectivity, and biological activity.

In the agricultural sector, 3-(Trifluoromethyl)benzoyl chloride finds application as a precursor for the synthesis of agrochemicals and pesticides. Fluorinated compounds exhibit enhanced pesticidal properties and metabolic stability. By incorporating 3-(Trifluoromethyl)benzoyl chloride into pesticide active ingredients, researchers aim to develop products that can effectively control pests, weeds, and fungal pathogens while minimizing environmental impact and non-target toxicity.

3-(Trifluoromethyl)benzoyl chloride is utilized in materials science for the synthesis of fluorinated polymers and specialty chemicals. Fluorine-containing compounds exhibit unique physical and chemical properties, such as high thermal stability, chemical resistance, and low surface energy, making them suitable for various industrial applications. 3-(Trifluoromethyl)benzoyl chloride serves as a building block for the production of fluorinated monomers, coatings, adhesives, and surfactants.

3-(Trifluoromethyl)benzoyl chloride is valuable as an intermediate in organic synthesis, facilitating the production of various chemical compounds with diverse applications. Its incorporation into multistep synthesis pathways enables the creation of complex molecules used in pharmaceuticals, agrochemicals, and materials science.

Beyond its established applications, ongoing research explores new uses for 3-(Trifluoromethyl)benzoyl chloride in fields such as medicinal chemistry, catalysis, and drug discovery. Scientists investigate its reactivity, properties, and potential interactions with biological targets to develop innovative therapies for treating diseases and disorders. technology, and industry.

References

2022. Reaction of a 2,3-Dihydrobenzo[b]phosphol-3-one with Electrophiles. *Science of Synthesis*.
URL: SD-110-02185

2019. Synthesis and characterization of novel fluorinated naphthalene-based poly(arylene ether ketone)s with low dielectric constants. *Journal of Materials Science: Materials in Electronics*, 30(17).
DOI: 10.1007/s10854-019-02008-2

2017. Discovery of tetrahydro-ß-carboline derivatives as a new class of phosphodiesterase 4 inhibitors. *Medicinal Chemistry Research*, 26(11).
DOI: 10.1007/s00044-017-2011-x