3-Bromo-1,1,1-trifluoroacetone
[CAS# 431-35-6]

Identification

• Classification: Chemical reagent >> Organic reagent >> Fatty ketone (including enol)
• Name: 3-Bromo-1,1,1-trifluoroacetone
• Synonyms: 1-Bromo-3,3,3-trifluoroacetone
• Molecular Formula: C₃H₂BrF₃O
• Molecular Weight: 190.95
• CAS Registry Number: 431-35-6
• EC Number: 207-071-9
• SMILES: C(C(=O)C(F)(F)F)Br

Properties

• Density: 1.8±0.1 g/cm³, Calc.^*, 1.839 g/mL (Expl.)
• Index of Refraction: 1.378, Calc.^*, 1.376 (Expl.)
• Boiling Point: 87.7 ºC (760 mmHg), Calc.^*, 87.8 ºC (Expl.)
• Flash Point: 5.0 ºC, Calc.^*, 5 ºC (Expl.)

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

Safety Data

• Hazard Symbols: GHS02;GHS06 Danger
• Hazard Statements: H225-H314
• Precautionary Statements: P210-P233-P240-P241-P242-P243-P260-P264-P280-P301+P330+P331-P302+P361+P354-P303+P361+P353-P304+P340-P305+P354+P338-P316-P321-P363-P370+P378-P403+P235-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Flammable liquids	Flam. Liq.	2	H225
Skin corrosion	Skin Corr.	1B	H314
Serious eye damage	Eye Dam.	1	H318
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Oxidising liquids	Ox. Liq.	2	H272
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410

• Transport Information: UN 2924

Discovory and Applicatios

3-Bromo-1,1,1-trifluoroacetone (C₃BrF₃O) is a halogenated organic compound that contains both a bromine atom and a trifluoromethyl group. It is known for its unique chemical structure, which consists of a trifluoroacetone backbone with a bromine atom attached at the 3-position of the carbon chain. This compound is a colorless or pale yellow liquid with a pungent odor and is typically used in chemical synthesis.

The synthesis of 3-bromo-1,1,1-trifluoroacetone generally involves the reaction of 1,1,1-trifluoroacetone with a brominating agent such as N-bromosuccinimide (NBS) or other bromine sources in the presence of a suitable solvent. The process results in the halogenation of the molecule, substituting a hydrogen atom for a bromine atom at the 3-position of the trifluoroacetone structure. This reaction is typically carried out under controlled conditions to ensure that the desired bromination occurs without causing excessive degradation of the product.

One of the main applications of 3-bromo-1,1,1-trifluoroacetone is in the field of organic synthesis, where it serves as an intermediate in the preparation of more complex molecules. The trifluoromethyl and bromine substituents make it a useful reagent for introducing both fluorine and bromine functionalities into organic compounds. This is particularly valuable in the synthesis of specialty chemicals, pharmaceuticals, and agrochemicals, where halogenation can influence the reactivity, stability, and biological activity of the final products.

In the pharmaceutical industry, 3-bromo-1,1,1-trifluoroacetone is utilized as a key building block for the synthesis of compounds with potential therapeutic applications. Its ability to selectively introduce both fluorine and bromine atoms into molecular structures makes it an important reagent for the modification of drug candidates. The incorporation of these halogens can affect the pharmacological properties of the molecules, such as their lipophilicity, metabolic stability, and binding affinity to biological targets.

In addition to its use in pharmaceutical synthesis, 3-bromo-1,1,1-trifluoroacetone is also employed in the production of agrochemicals. The compound can be used in the synthesis of plant protection agents, herbicides, and insecticides, where the incorporation of fluorine and bromine atoms can enhance the potency and selectivity of the active ingredients. The trifluoromethyl group, in particular, is known to improve the stability and persistence of agrochemicals in the environment, making them more effective in agricultural applications.

Furthermore, 3-bromo-1,1,1-trifluoroacetone finds use in the development of advanced materials, particularly those involving fluorine chemistry. The compound's unique structure allows it to serve as a precursor to materials with enhanced chemical resistance, electrical conductivity, and thermal stability. It can be used in the preparation of specialty polymers, coatings, and other materials that require the distinct properties imparted by fluorine and bromine substitution.

The safety and handling of 3-bromo-1,1,1-trifluoroacetone require caution, as the compound is reactive due to the presence of both bromine and fluorine atoms. Proper protective measures should be taken to prevent inhalation, skin contact, or ingestion of the chemical. It is also important to handle the compound in well-ventilated areas and to follow appropriate disposal procedures to minimize environmental impact.

In summary, 3-bromo-1,1,1-trifluoroacetone is a versatile halogenated compound with significant applications in organic synthesis, pharmaceuticals, agrochemicals, and materials science. Its unique combination of bromine and trifluoromethyl groups makes it an important reagent for the synthesis of halogenated organic molecules with desirable chemical and biological properties. Through its role as an intermediate in the preparation of complex compounds, 3-bromo-1,1,1-trifluoroacetone continues to be a valuable tool in the development of new and innovative chemical products.

References

2020. A suite of 19F based relaxation dispersion experiments to assess biomolecular motions. Journal of Biomolecular NMR, 74(12).
DOI: 10.1007/s10858-020-00348-4

2019. Feasibility of trifluoromethyl TROSY NMR at high magnetic fields. Journal of Biomolecular NMR, 73(6-7).
DOI: 10.1007/s10858-019-00266-0

2017. Solvent-accessibility of discrete residue positions in the polypeptide hormone glucagon by 19F-NMR observation of 4-fluorophenylalanine. Journal of Biomolecular NMR, 68(2).
DOI: 10.1007/s10858-017-0107-8