2-Bromobenzotrifluoride
[CAS# 392-83-6]

Identification

• Classification: Organic raw materials >> Organic fluorine compound >> Fluorotoluene series
• Name: 2-Bromobenzotrifluoride
• Synonyms: 1-Bromo-2-(trifluoromethyl)benzene; o-Bromobenzotrifluoride
• Molecular Formula: C₇H₄BrF₃
• Molecular Weight: 225.01
• CAS Registry Number: 392-83-6
• EC Number: 206-879-9
• SMILES: C1=CC=C(C(=C1)C(F)(F)F)Br

Properties

• Density: 1.652
• Boiling point: 167-168 °C
• Refractive index: 1.481-1.483
• Flash point: 51 °C

Safety Data

• Hazard Symbols: GHS02;GHS07 Warning
• Risk Statements: H226-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
Flammable liquids	Flam. Liq.	3	H226
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2A	H319

• Transport Information: UN 1993

Discovery and Applications

2-Bromotrifluoroanisole (2-BBT), with the chemical formula C7H4BrF3, is an aromatic compound characterized by a bromine atom and a trifluoromethyl group attached to a benzene ring. The compound, also known as α-bromo-α,α,α-trifluorotoluene, is a colorless to pale yellow liquid at room temperature and is known for its unique combination of bromine and trifluoromethyl substituents.

The synthesis of 2-bromotrifluoroanisole can be traced back to the development of organofluorine chemistry in the mid-20th century. The introduction of the trifluoromethyl group into aromatic compounds was a major breakthrough, primarily due to the need for new materials with desirable chemical and physical properties such as enhanced stability and hydrophobicity. The compound is typically synthesized via the bromination of trifluorotoluene, with trifluorotoluene as the starting material, and the bromine is introduced via electrophilic aromatic substitution.

2-Bromotrifluorotoluene is a valuable intermediate in drug synthesis. Its bromine atom can be substituted with various functional groups, resulting in a wide range of molecules with potential therapeutic effects. The trifluoromethyl group also imparts metabolic stability and lipophilicity, which is beneficial in drug design.

In the agrochemical industry, 2-BBT is used to produce herbicides, fungicides, and insecticides. The trifluoromethyl group enhances the biological activity of these compounds, making them more effective at lower doses.

The chemical is used to develop advanced materials. Its stability and reactivity make it suitable for making polymers and resins with special properties. These materials can be used in coatings, adhesives, and electronic components.

2-Bromotrifluoroanisole is a versatile organic synthetic building block. It participates in cross-coupling reactions such as the Suzuki-Miyaura reaction and the Heck reaction to form carbon-carbon bonds. These reactions are the basis for building complex organic molecules for various applications, including pharmaceuticals and fine chemicals.

The compound is also used in academic and industrial research to explore new chemical reactions and mechanisms. Its unique structure serves as a model for studying the effects of bromine and trifluoromethyl groups on aromatic systems.

While 2-Bromotrifluoroanisole is a valuable chemical, it needs to be handled with care. It can cause skin and eye irritation and should be used in well-ventilated areas with appropriate personal protective equipment. Proper storage conditions are also essential to prevent degradation and ensure safety.

References

2024. Efficient “One-Column” grignard generation and reaction in continuous flow. Journal of Flow Chemistry, 14(4).
DOI: 10.1007/s41981-024-00332-1

2013. Scope of the Desulfinylative Palladium-Catalyzed Cross-Coupling of Aryl Sulfinates with Aryl Bromides. Synthesis, 45(6).
DOI: 10.1055/s-0032-1318151

2003. Bromine as the Ortho-Directing Group in the Aromatic Metalation/Silylation of Substituted Bromobenzenes. The Journal of Organic Chemistry, 68(22).
DOI: 10.1021/jo034790h