3-Fluorobenzotrifluoride
[CAS# 401-80-9]

Identification

• Classification: Organic raw materials >> Organic fluorine compound >> Fluorotoluene series
• Name: 3-Fluorobenzotrifluoride
• Synonyms: 1-Fluoro-3-(trifluoro-methyl)benzene; alpha,alpha,alpha,3-Tetrafluorotoluene
• Molecular Formula: C₇H₄F₄
• Molecular Weight: 164.10
• CAS Registry Number: 401-80-9
• EC Number: 206-933-1
• SMILES: C1=CC(=CC(=C1)F)C(F)(F)F

Properties

• Density: 1.302 g/mL
• Melting point: -81.5 °C
• Boiling point: 101-102 °C
• Refractive index: 1.3997-1.4017
• Flash point: 7 °C

Safety Data

• Hazard Symbols: GHS02;GHS07 Danger
• Risk Statements: H225-H315-H319-H335
• Safety Statements: P210-P233-P240-P241-P242-P243-P261-P264-P264+P265-P271-P280-P302+P352-P303+P361+P353-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P370+P378-P403+P233-P403+P235-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Flammable liquids	Flam. Liq.	2	H225

• Transport Information: UN 1993

Discovery and Applications

3-Fluorobenzotrifluoride is a fluorinated aromatic compound that has gained attention in various fields of chemical research, including organic synthesis, materials science, and medicinal chemistry. This compound is a member of the benzenesulfonyl fluoride family, characterized by a benzene ring with a fluorine atom and three trifluoromethyl groups attached. The unique properties of 3-fluorobenzotrifluoride arise from the presence of both the fluorine and trifluoromethyl substituents, which significantly influence its reactivity and stability.

The discovery of 3-fluorobenzotrifluoride can be traced back to the exploration of fluorinated compounds in the mid-20th century. As chemists began to recognize the importance of fluorine in enhancing the physicochemical properties of organic molecules, compounds like 3-fluorobenzotrifluoride emerged as valuable intermediates for synthesizing more complex structures. The synthetic routes to produce this compound often involve the fluorination of benzotrifluoride, which can be achieved using various fluorinating agents under controlled conditions to ensure the correct positioning of the fluorine atom.

One of the primary applications of 3-fluorobenzotrifluoride lies in the field of organic synthesis. The presence of multiple electronegative fluorine atoms in its structure enhances its electrophilic character, making it a useful building block for the synthesis of various pharmaceuticals and agrochemicals. The compound can participate in various chemical reactions, such as nucleophilic substitutions and electrophilic aromatic substitutions, enabling the introduction of additional functional groups into the molecular framework. This versatility makes it an essential component in developing more complex chemical entities with specific biological activities.

In medicinal chemistry, 3-fluorobenzotrifluoride has been studied for its potential as a lead compound in drug discovery. The fluorine substituents often enhance the metabolic stability and bioavailability of drug candidates. As a result, derivatives of 3-fluorobenzotrifluoride have been synthesized and evaluated for their biological activities against various targets, including enzymes and receptors involved in disease processes. Research has indicated that these derivatives exhibit promising pharmacological properties, leading to their consideration as potential therapeutic agents.

Furthermore, 3-fluorobenzotrifluoride has applications in materials science, particularly in developing high-performance polymers and coatings. The unique chemical properties imparted by the fluorinated structure contribute to the thermal stability and chemical resistance of the resulting materials. As a result, 3-fluorobenzotrifluoride is utilized in producing specialty chemicals and materials designed for specific industrial applications.

In summary, 3-fluorobenzotrifluoride is a significant fluorinated compound with diverse applications across organic synthesis, medicinal chemistry, and materials science. Its discovery and subsequent investigation have opened new avenues for the development of advanced chemical entities, underscoring the importance of fluorinated compounds in contemporary chemical research.

References

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2019. One-Pot Approach for SNAr Reaction of Fluoroaromatic Compounds with Cyclopropanol. Synlett, 30.
DOI: 10.1055/s-0037-1611768