3,5-Bis(trifluoromethyl)bromobenzene
[CAS# 328-70-1]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound >> Pyridine derivative
• Name: 3,5-Bis(trifluoromethyl)bromobenzene
• Synonyms: 3,5-Bis(trifluoromethyl)-1-bromobenzene; 1-Bromo-3,5-bis-(trifluoromethyl)benzene
• Molecular Formula: C₈H₃BrF₆
• Molecular Weight: 293.01
• CAS Registry Number: 328-70-1
• EC Number: 206-334-5
• SMILES: C1=C(C=C(C=C1C(F)(F)F)Br)C(F)(F)F

Properties

• Density: 1.71
• Melting point: -16 °C
• Boiling point: 154 °C
• Refractive index: 1.426-1.428
• Flash point: 112 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413

Discovery and Applications

3,5-Bis(trifluoromethyl)bromobenzene is an organic compound that was first synthesized in the mid-20th century during the exploration of halogenated aromatic compounds. Its discovery was part of broader research efforts aimed at developing new materials and chemicals with unique properties for industrial and pharmaceutical applications. The introduction of trifluoromethyl groups into the benzene ring, combined with a bromine atom, provided this compound with distinctive chemical properties that made it valuable for various synthetic processes. Over the years, its utility in chemical synthesis has been extensively studied and applied in various fields.

One of the primary applications of 3,5-Bis(trifluoromethyl)bromobenzene is in the pharmaceutical industry. It serves as a valuable building block in the synthesis of various pharmaceutical compounds. The presence of trifluoromethyl groups enhances the lipophilicity and metabolic stability of drug molecules, often leading to improved pharmacokinetic properties. This compound is utilized in the development of drugs targeting various conditions, including cardiovascular diseases, neurological disorders, and cancers. Its ability to facilitate the formation of complex molecules makes it an indispensable tool in medicinal chemistry.

In the field of agrochemicals, 3,5-Bis(trifluoromethyl)bromobenzene is used in the synthesis of herbicides, fungicides, and insecticides. The trifluoromethyl group imparts unique physicochemical properties that enhance the effectiveness and durability of agrochemical products. These properties include increased resistance to metabolic degradation and improved ability to penetrate plant tissues. As a result, compounds derived from 3,5-Bis(trifluoromethyl)bromobenzene are more effective in protecting crops from pests and diseases, thereby contributing to higher agricultural productivity.

Material science is another domain where 3,5-Bis(trifluoromethyl)bromobenzene finds significant application. Its incorporation into polymers and other materials imparts desirable properties such as enhanced thermal stability, chemical resistance, and hydrophobicity. These characteristics are particularly valuable in the development of high-performance materials for use in harsh environments. For example, it is used in the production of specialty coatings, electronic materials, and advanced composites, which require robust performance under extreme conditions.

In chemical research, 3,5-Bis(trifluoromethyl)bromobenzene is employed as a reagent and intermediate in various organic synthesis reactions. Its unique structure allows for the introduction of trifluoromethyl groups into target molecules, which can significantly alter their chemical behavior and properties. This compound is used in cross-coupling reactions, such as Suzuki and Stille couplings, to form carbon-carbon bonds, facilitating the creation of complex organic molecules. Researchers utilize it to explore new synthetic pathways and develop novel compounds with potential applications in various industries.

Environmental and industrial chemistry also benefit from the use of 3,5-Bis(trifluoromethyl)bromobenzene. Its stability and resistance to chemical degradation make it useful in creating environmentally durable materials. For instance, it is used in the synthesis of fluoropolymers and other materials that need to withstand corrosive environments and high temperatures. These materials are employed in a range of industrial applications, including chemical processing equipment, gaskets, and seals.

References

2013. Organotrifluoroborate Coupling. Organotrifluoroborate Preparation, Coupling and Hydrolysis, Not applicable.
DOI: 10.1007/978-3-319-01134-9_3

2010. Aryl Bromides in Suzuki Cross-Coupling Reactions. Science of Synthesis, Not applicable.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-045-00519

2012. Palladium-Catalyzed Coupling Reactions. Science of Synthesis, Not applicable.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-208-00098