2-Bromo-4'-(trifluoromethyl)acetophenone: Properties & Uses

2-Bromo-4'-(trifluoromethyl)acetophenone is a versatile α-haloketone building block bearing an electron-withdrawing trifluoromethyl group, widely employed in pharmaceutical and agrochemical synthesis for the construction of heterocyclic scaffolds and fluorinated bioactive compounds.

Chemical Name

2-Bromo-4'-(trifluoromethyl)acetophenone

CAS Number

383-53-9

Molecular Formula

C9H6BrF3O

Molecular Weight

267.04 g/mol

Key Functional Groups

α-bromoketone, trifluoromethyl arene

Primary Application

Heterocycle synthesis; pharmaceutical intermediate

SKU

B152258 (Aladdin Scientific)

Chemical Identity and Physical Properties

2-Bromo-4'-(trifluoromethyl)acetophenone (CAS 383-53-9) is an α-bromoacetophenone derivative characterized by a reactive bromomethylene unit adjacent to the carbonyl and a para-trifluoromethyl substituent on the aryl ring. Its molecular formula is C₉H₆BrF₃O, with a molecular weight of approximately 267.04 g/mol.

The trifluoromethyl group (–CF₃) is strongly electron-withdrawing by both induction and hyperconjugation, significantly increasing the electrophilicity of the carbonyl carbon and the α-carbon bearing bromine. This dual activation makes the compound a highly reactive electrophilic synthon. The compound typically presents as a white to off-white solid or low-melting crystalline material. Specific melting point, boiling point, and solubility data should be confirmed against the certificate of analysis supplied with each lot.

Synthesis Applications and Reactivity

The α-bromoketone functionality renders 2-Bromo-4'-(trifluoromethyl)acetophenone an exceptionally useful building block in organic synthesis. Its primary synthetic utility arises from two electrophilic sites: the α-carbon bearing bromine (susceptible to S_N2 displacement by nucleophiles) and the activated carbonyl (amenable to condensation reactions).

Heterocycle Synthesis: This compound is a classical precursor for the construction of five-membered nitrogen- and oxygen-containing heterocycles. Reactions with thioamides or thioureas yield thiazole derivatives; condensation with amidines affords oxazoles; and treatment with hydrazines or semicarbazides provides access to pyrazole and related scaffolds. The trifluoromethyl group is retained throughout these transformations, delivering fluorinated heterocycles with enhanced metabolic stability and membrane permeability — properties highly valued in drug discovery.

Alkylation Reactions: The activated C–Br bond undergoes efficient alkylation of malonate esters, β-ketoesters, and other stabilized carbanions, enabling rapid assembly of complex carbon frameworks.

Pharmaceutical Intermediates: Fluorinated aryl ketones of this class serve as key intermediates in the preparation of kinase inhibitors, antimicrobial agents, and other bioactive small molecules where the –CF₃ group improves pharmacokinetic profiles.

Safety, Handling, and Storage

Hazard Profile: As an α-haloketone, 2-Bromo-4'-(trifluoromethyl)acetophenone is a lachrymatory and potentially irritating compound. It should be treated as a skin, eye, and respiratory irritant. Consult the Safety Data Sheet (SDS) for full GHS hazard classifications before use. Work in a well-ventilated fume hood at all times.

Personal Protective Equipment (PPE): Chemical-resistant gloves (nitrile or neoprene), laboratory coat, and safety goggles are the minimum requirements. A half-face respirator with organic vapour cartridges is recommended when handling larger quantities or when ventilation is limited.

Storage: Store in a cool, dry location away from light, moisture, and incompatible reagents such as strong bases and reducing agents. The compound is moisture-sensitive; keep the container tightly sealed under an inert atmosphere (nitrogen or argon) when not in use. Recommended storage temperature is 2–8 °C or as specified on the product label. Check the certificate of analysis for lot-specific stability data.

Disposal: Dispose of waste material in accordance with local and national regulations governing halogenated organic compounds.

Quality and Specifications

Aladdin Scientific offers 2-Bromo-4'-(trifluoromethyl)acetophenone (SKU: B152258) to support demanding research applications. Each lot is characterized by standard analytical techniques including:

• Purity: Assessed by GC or HPLC; specific purity grade is stated on the product page and certificate of analysis.
• Identity Confirmation: ¹H NMR and/or ¹⁹F NMR spectroscopy, confirming the α-bromo carbonyl and –CF₃ resonances.
• Appearance: Visual inspection for colour and physical form consistent with specification.

Researchers requiring custom quantities, higher purity grades, or isotopically labelled analogues are encouraged to contact Aladdin Scientific's technical sales team. A certificate of analysis is available for every lot upon request.

Frequently asked questions

What is 2-Bromo-4'-(trifluoromethyl)acetophenone used for in synthesis?

It is primarily used as an electrophilic building block for the synthesis of fluorinated heterocycles, including thiazoles, oxazoles, and pyrazoles, via condensation with appropriate dinucleophiles. It also serves as a pharmaceutical intermediate, enabling installation of the metabolically stable –CF3 group into bioactive scaffolds.

How should 2-Bromo-4'-(trifluoromethyl)acetophenone be stored to ensure stability?

The compound is moisture-sensitive and should be stored in a tightly sealed container under an inert atmosphere (nitrogen or argon) in a cool, dark, and dry environment, ideally at 2–8 °C. Avoid contact with strong bases, reducing agents, and water.

What safety precautions are required when handling this compound?

Because it is an α-haloketone with potential lachrymatory and irritant properties, all handling should be performed in a fume hood with nitrile or neoprene gloves, a lab coat, and safety goggles. Consult the full SDS before use and dispose of waste according to local regulations for halogenated organics.

What nucleophiles react with 2-Bromo-4'-(trifluoromethyl)acetophenone to form thiazoles?

Thioamides and thiourea derivatives are classic dinucleophiles that react with α-bromoketones via Hantzsch-type cyclization to give 2-aminothiazole or 2-substituted thiazole products bearing the 4-(trifluoromethyl)phenyl group at the 4-position of the ring.

Is 2-Bromo-4'-(trifluoromethyl)acetophenone available in multiple purity grades?

Aladdin Scientific lists this compound under SKU B152258. For information on available purity grades or custom specifications, researchers should consult the current product page or contact the technical sales team directly.

References

1. Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry, 2nd ed.; Oxford University Press: Oxford, 2012. (General reference for α-haloketone reactivity and heterocycle synthesis.)
2. Manske, R. H. F.; Kulka, M. The Hantzsch Thiazole Synthesis. Organic Reactions 1953, 7, 59–98. (Classical method for thiazole formation from α-haloketones.)
3. Muller, K.; Faeh, C.; Diederich, F. Fluorine in Pharmaceuticals: Looking Beyond Intuition. Science 2007, 317, 1881–1886. doi:10.1126/science.1131943

Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.