2-Bromo-3,3,3-trifluoropropene
[CAS# 1514-82-5]

Identification

• Classification: Chemical reagent >> Organic reagent >> Halogenated aliphatic hydrocarbon
• Name: 2-Bromo-3,3,3-trifluoropropene
• Synonyms: 2-Bromo-3,3,3-trifluoro-1-propene
• Molecular Formula: C₃H₂BrF₃
• Molecular Weight: 174.95
• CAS Registry Number: 1514-82-5
• EC Number: 627-872-0
• SMILES: C=C(C(F)(F)F)Br

Properties

• Density: 1.7±0.1 g/cm³, Calc.^*, 1.686 g/mL (Expl.)
• Index of Refraction: 1.379, Calc.^*, 1.35 (Expl.)
• Boiling Point: 77.9±35.0 °C (760 mmHg), Calc.^*, 33-33.5 °C (Expl.)
• Flash Point: -15.3±21.8 °C, Calc.^*, -10 °C (Expl.)

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

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
Flammable liquids	Flam. Liq.	1	H224
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H302
Specific target organ toxicity - single exposure	STOT SE	3	H335
Reproductive toxicity	Repr.	2	H361
Germ cell mutagenicity	Muta.	2	H341
Specific target organ toxicity - single exposure	STOT SE	3	H336
Self-reactive substances or mixtures	Self-react.	F	H242
Skin irritation	Skin Irrit.	2	H315
Flammable liquids	Flam. Liq.	2	H225
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

2-Bromo-3,3,3-trifluoropropene (C₃H₂BrF₃) is a halogenated olefin that has been studied for its applications in organic synthesis and industrial chemistry. This compound belongs to the class of trifluoropropenes, which are characterized by the presence of both a bromine and trifluoromethyl (-CF₃) group attached to a carbon-carbon double bond. The presence of these electronegative substituents significantly influences its reactivity and physical properties.

The synthesis of 2-bromo-3,3,3-trifluoropropene has been documented in the literature, typically involving the halogenation of fluorinated precursors. One common route includes the reaction of trifluoropropene derivatives with brominating agents such as N-bromosuccinimide (NBS) or molecular bromine (Br₂) under controlled conditions. The introduction of the bromine atom at the 2-position provides a reactive site for further transformations, making this compound useful as a synthetic intermediate.

In industrial applications, 2-bromo-3,3,3-trifluoropropene is used as a building block for the synthesis of fluorinated materials. Its structure allows for facile functionalization through nucleophilic substitution, metal-catalyzed coupling reactions, and polymerization processes. Fluorinated compounds derived from this molecule are important in the production of refrigerants, agrochemicals, and pharmaceuticals, where the trifluoromethyl group imparts desirable properties such as increased stability, lipophilicity, and bioavailability.

In organic synthesis, 2-bromo-3,3,3-trifluoropropene serves as a precursor for the introduction of trifluoromethyl and brominated functionalities into complex molecules. The bromine atom enables cross-coupling reactions such as the Suzuki-Miyaura and Heck reactions, facilitating the formation of carbon-carbon bonds with a variety of nucleophiles and organometallic reagents. The trifluoromethyl-substituted alkene moiety can also participate in hydrofunctionalization and cycloaddition reactions, expanding its versatility in synthetic applications.

The handling and storage of 2-bromo-3,3,3-trifluoropropene require caution due to its potential reactivity and volatility. It should be stored in a tightly sealed container under an inert atmosphere to prevent unwanted reactions with moisture or oxygen. Like other halogenated alkenes, it may exhibit toxicity upon prolonged exposure, necessitating appropriate safety measures, including the use of personal protective equipment and adequate ventilation in laboratory and industrial settings.

The continued interest in fluorinated compounds for advanced materials and pharmaceutical applications ensures that 2-bromo-3,3,3-trifluoropropene remains relevant in research and industry. Its well-documented role as a synthetic intermediate highlights its importance in the development of functionalized fluorinated molecules.

References

2021. Continuous flow synthesis of Celecoxib from 2-bromo-3,3,3-trifluoropropene. Journal of Flow Chemistry, 11(3).
DOI: 10.1007/s41981-021-00205-x

1989. Synthesis of vicinal bromoalkylamines containing a trifluoromethyl group. Bulletin of the Academy of Sciences of the USSR, Division of chemical science, 38(2).
DOI: 10.1007/bf00953647