Bromodifluoroacetic acid
[CAS# 354-08-5]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Carboxylic acid
• Name: Bromodifluoroacetic acid
• Synonyms: Difluorobromoacetic acid
• Molecular Formula: C₂HBrF₂O₂
• Molecular Weight: 174.93
• CAS Registry Number: 354-08-5
• EC Number: 674-544-8
• SMILES: C(=O)(C(F)(F)Br)O

Properties

• Melting point: 52-56 °C
• Boiling point: 134 °C

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Risk Statements: H302-H312-H314-H332
• Safety Statements: P260-P261-P264-P270-P271-P280-P301+P317-P301+P330+P331-P302+P352-P302+P361+P354-P304+P340-P305+P354+P338-P316-P317-P321-P330-P362+P364-P363-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Skin corrosion	Skin Corr.	1B	H314
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H312
Skin corrosion	Skin Corr.	1	H314

Discovery and Applications

Bromodifluoroacetic acid is a halogenated organic compound with significant applications in organic synthesis, environmental chemistry, and analytical research. The compound is characterized by a bromine atom attached to a carbon atom, which is also bonded to two fluorine atoms and a carboxyl group. This structure makes it a versatile reagent in chemical reactions and a subject of interest for environmental studies due to its potential role as a disinfection byproduct in water treatment processes.

The discovery of bromodifluoroacetic acid is tied to research in the development of halogenated acetic acids for their reactivity and ability to act as intermediates in organic synthesis. Its unique combination of bromine and fluorine atoms contributes to its chemical reactivity, making it useful in reactions that require halogenated acids as catalysts or reactants. Bromodifluoroacetic acid is employed in the preparation of various fluorinated compounds, which are important in pharmaceutical and agrochemical research. Fluorine-containing compounds often exhibit enhanced biological activity, and bromodifluoroacetic acid serves as a valuable building block in this context.

In environmental chemistry, bromodifluoroacetic acid has gained attention as a byproduct of water disinfection processes, particularly those involving brominated and fluorinated compounds. During the chlorination of water supplies, bromide ions can react with chlorine and organic matter to form brominated acetic acids, including bromodifluoroacetic acid. Its presence in drinking water raises concerns about its potential health effects, leading to studies on its occurrence, behavior, and removal from water supplies.

Bromodifluoroacetic acid also finds applications in analytical chemistry. Due to its distinct halogenated structure, it can be used as a reference standard or reagent in chromatographic and spectrometric analyses. Its chemical properties make it suitable for the calibration of instruments that detect and quantify halogenated organic compounds.

The applications of bromodifluoroacetic acid in both synthetic and environmental contexts highlight its importance. While it serves as a useful reagent in the laboratory, ongoing research continues to explore its impact as a byproduct of water disinfection, emphasizing the need for effective monitoring and control in public health contexts.

References

2018. Fluorinated Carboxylic Acids in Synthesis. Journal of Fluorine Chemistry, 211.
DOI: 10.1016/j.jfluchem.2018.04.003