4-Bromophenacyl-trifluoromethanesulfonate is a brominated phenacyl triflate derivative featuring a 4-bromophenacyl moiety linked to a trifluoromethanesulfonate (triflate) leaving group, placing it in the class of activated sulfonate esters rather than free amino acids or peptide intermediates. The molecule contains an aromatic ring bearing a bromine substituent, a carbonyl-containing phenacyl framework, and a sulfonate ester functional group that can undergo substitution reactions under appropriate conditions, with stereochemistry not specified by the provided name. In synthetic and chemical biology workflows, this activated electrophile is commonly employed as a reagent for introducing the phenacyl group or for generating labeled or derivatized products through controlled reactions with nucleophiles, supporting preparation of more complex aromatic or carbonyl-adjacent derivatives for analytical method development and structure-activity studies.
CAT No: CP27591
CAS No:93128-04-2
Synonyms/Alias:4-Bromophenacyltriflate;93128-04-2;2-(4-bromophenyl)-2-oxoethyltrifluoromethanesulfonate;4'-Bromophenacyltriflate;4-Bromophenacyltrifluoromethanesulfonate;Methanesulfonicacid,trifluoro-,2-(4-bromophenyl)-2-oxoethylester;BPTSE;C9H6BrF3O4S;AC1L2NU4;AC1Q1H24;SCHEMBL14351624;41392_FLUKA;CTK8D8782;MolPort-003-932-283;5583AH;AR-1J4084;ZINC71788589;AKOS016845945;4-BROMOPHENACYL-TRIFLUOROMESYLATE;4'-Bromophenacyltrifluoromethanesulfonate;AK135109;EN002847;OR008374;OR377385;KB-222384
4-Bromophenacyl-trifluoromethanesulfonate is a reactive aryl bromide sulfonate ester designed for chemical labeling and derivatization workflows where fast electrophilic capture is advantageous. As a halomethyl/aryl electrophile bearing a trifluoromethanesulfonate leaving group, it is commonly handled as a specialized reagent for introducing a bromophenacyl motif onto nucleophilic targets, enabling downstream detection, purification, or immobilization strategies in chemical biology and analytical chemistry. Researchers typically select this reagent when they need a robust, non-biological intermediate that can be coupled to amine- or thiol-containing substrates under controlled conditions.
1. Chemical Derivatization Reagent
4-Bromophenacyl-trifluoromethanesulfonate is used as a derivatization reagent to functionalize nucleophilic biomolecule components in analytical and research settings, including labeling of amine- and thiol-bearing targets for subsequent separation or readout. Chemical biology groups and analytical chemistry teams often employ it to install a bromophenacyl group that can improve detectability or create a handle for follow-on processing. The triflate leaving group supports efficient electrophilic substitution, making the reagent useful when a strong coupling step is required before LC-MS, electrophoresis, or chromatographic analysis.
2. Bioconjugation Linker Development
4-Bromophenacyl-trifluoromethanesulfonate finds application in bioconjugation development where researchers need a chemically defined way to attach a reactive aryl bromide motif to biomolecular scaffolds. Protein chemistry and chemical biology laboratories use it during method development for preparing labeled proteins, peptide conjugates, or functionalized biomolecular probes that require a specific electrophilic group for downstream transformations. In these workflows, the reagent is valued for its clear chemical identity and reactivity profile, enabling reproducible conjugation chemistry during probe or conjugate synthesis.
3. Analytical LC-MS Labeling
4-Bromophenacyl-trifluoromethanesulfonate is applied in analytical method development to generate derivatized analytes that behave differently in chromatographic systems and mass spectrometric detection. Proteomics-adjacent and metabolomics-focused laboratories may use it to derivatize selected functional groups to improve signal characteristics, facilitate identification, or support targeted quantitation strategies using LC-MS workflows. The bromophenacyl motif and the sulfonate leaving group contribute to consistent derivatization chemistry, which is important when building reliable analytical standards or preparing sample sets for comparative studies.
4. Solid-Phase Immobilization Chemistry
4-Bromophenacyl-trifluoromethanesulfonate is also used in immobilization chemistry to incorporate a reactive aryl bromide functionality onto solid supports or polymeric materials that present nucleophilic binding sites. Materials science and chemical engineering teams employ it when they need stable, covalent attachment of a defined electrophilic group to surfaces for subsequent capture, affinity workflows, or further chemical modification. The reagent's electrophilic character supports coupling steps that can be integrated into surface functionalization protocols for research-grade biomaterials and affinity reagent development.
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