Description

4′-Bromo-2,2,2-trifluoroacetophenone (CAS No. 16184-89-7) is a high-purity brominated trifluoroacetophenone derivative with the molecular formula C₈H₄BrF₃O. This compound, also known by its IUPAC name 1-(4-bromophenyl)-2,2,2-trifluoroethanone, is a versatile building block in organic synthesis and pharmaceutical research. Its unique structure, featuring a bromine substituent at the para position and a trifluoromethyl ketone moiety, makes it valuable for nucleophilic aromatic substitution reactions, cross-coupling reactions, and as a precursor for fluorinated intermediates. The compound is supplied as a crystalline solid with ≥98% purity (GC), ensuring consistency for sensitive applications. Proper storage under inert conditions is recommended to maintain stability.

Properties

• CAS Number: 16184-89-7
• Complexity: 194
• IUPAC Name: 1-(4-bromophenyl)-2,2,2-trifluoro-ethanone
• InChI: InChI=1S/C8H4BrF3O/c9-6-3-1-5(2-4-6)7(13)8(10,11)12/h1-4H
• InChI Key: IHGSAQHSAGRWNI-UHFFFAOYSA-N
• Exact Mass: 251.93976
• Molecular Formula: C8H4BrF3O
• Molecular Weight: 253.02
• SMILES: C1=CC(=CC=C1C(=O)C(F)(F)F)Br
• Topological: 17.1
• Monoisotopic Mass: 251.93976
• Synonyms: 4′-Bromo-2,2,2-trifluoroacetophenone, 16184-89-7, DTXSID00345342, DTXCID50296416, 629-304-7, 1-(4-Bromophenyl)-2,2,2-trifluoroethanone, Ethanone, 1-(4-bromophenyl)-2,2,2-trifluoro-, 1-(4-bromophenyl)-2,2,2-trifluoroethan-1-one, 1-(4-Bromo-phenyl)-2,2,2-trifluoro-ethanone, MFCD00191862, 2,2,2-TRIFLUORO-4′-BROMOACETOPHENONE, 4-Trifluoroacetylbromobenzene, SCHEMBL17216, 4 inverted exclamation mark -Bromo-2,2,2-trifluoroacetophenone, BCP27420, CS-M1418, BBL101766, CL8645, SBB101196, STL555563, 4′-Bromo-2,2,2-trifluoracetophenone, AKOS005258375, 4′-bromo-2,2,2-trifluoroaceto-phenone, 4′-Bromo-2,2,2-trifluoroacetophenone, AS-18874, SY023310, DB-120953, ST51038297, EN300-42858, 1-(4-Bromophenyl)-2,2,2-trifluoroethanone #, 4′-Bromo-2,2,2-trifluoroacetophenone, >=98%, 4 inverted exclamation marka-Bromo-2,2,2-trifluoroacetophenone, 4′-Bromo-2,2,2-trifluoroacetophenone, purum, >=98.0% (GC)

Application

4′-Bromo-2,2,2-trifluoroacetophenone is widely used as a key intermediate in the synthesis of pharmaceuticals, agrochemicals, and specialty materials. Its reactivity enables the preparation of trifluoromethylated compounds with enhanced biological activity or metabolic stability. Researchers employ this compound in Suzuki-Miyaura and other palladium-catalyzed cross-coupling reactions to construct complex fluorinated aromatics. It also serves as a precursor for ligands and catalysts in asymmetric synthesis.

Safety and Hazards

GHS Hazard Statements

• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (97.9%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary 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, and P501

Hazard Classes and Categories

• Skin Irrit. 2 (100%)
• Eye Irrit. 2 (100%)
• STOT SE 3 (97.9%)

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