1,1-Dibromo-3,3,3-trifluoroacetone
[CAS# 431-67-4]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Ketones
• Name: 1,1-Dibromo-3,3,3-trifluoroacetone
• Synonyms: 3,3-dibromo-1,1,1-trifluoropropan-2-one
• Molecular Formula: C₃HBr₂F₃O
• Molecular Weight: 269.84
• CAS Registry Number: 431-67-4
• EC Number: 638-897-1
• SMILES: C(C(=O)C(F)(F)F)(Br)Br

Properties

• Density: 1.98 g/mL
• Boiling point: 111-113 °C (10 torr)
• Refractive index: 1.4305

Safety Data

• Hazard Symbols: GHS02;GHS07 Warning
• Risk Statements: H290-H302-H312-H314-H318-H332
• Safety Statements: P234-P260-P261-P264-P264+P265-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-P390-P405-P406-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin corrosion	Skin Corr.	1B	H314
Serious eye damage	Eye Dam.	1	H318
Acute toxicity	Acute Tox.	4	H312
Substances or mixtures corrosive to metals	Met. Corr.	1	H290
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H302

Discovery and Applications

1,1-Dibromo-3,3,3-trifluoroacetone (DBTFA) is a haloketone with the chemical formula C₃HBr₂F₃O and a molecular weight of 255.84 g/mol. It has a trifluoromethyl group and two bromine atoms attached to the same carbon adjacent to the carbonyl group, making it a reactive compound that can be used in a variety of chemical syntheses.

The development of DBTFA can be attributed to the advancement of halogenated organic compounds in the 20th century. It was synthesized as part of an effort to create highly reactive intermediates for organic synthesis, particularly in the fields of pharmaceuticals and agrochemicals. The synthesis typically involves the bromination of trifluoroacetone, yielding a highly electrophilic ketone that can participate in a variety of chemical transformations.

1,1-Dibromo-3,3,3-trifluoroacetone is synthesized by bromination of trifluoroacetone under controlled conditions. The synthesis yields DBTFA, which is highly reactive due to the presence of both bromine and trifluoromethyl groups, making it a valuable intermediate for further chemical modifications.

DBTFA is widely used in organic synthesis as a building block for introducing trifluoromethyl and bromine atoms into target molecules. Its reactivity enables the formation of complex molecules through nucleophilic and electrophilic reactions, facilitating the development of various pharmaceuticals and agrochemicals.

In pharmaceuticals, DBTFA is used as a precursor for the synthesis of compounds with potential therapeutic applications. It is able to introduce trifluoromethyl groups to enhance metabolic stability and bioavailability, making it an important intermediate in drug development.

In agrochemicals, DBTFA is used in the synthesis of pesticides and herbicides. The trifluoromethyl group contributes to the biological activity of these compounds, which can more effectively control pests and enhance crop protection.

DBTFA can be used as a reagent in research laboratories to study reaction mechanisms and develop new synthetic methods. Its unique structure allows chemists to explore various reaction pathways and create novel compounds with a variety of applications.

References

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