Ac-p-bromo-DL-Phe-OH is an N-acetylated, para-bromo-substituted phenylalanine derivative (DL indicates a racemic mixture) bearing a benzyl side chain with a p-bromine substituent and the aromatic ring characteristic of phenylalanine. The molecule contains an acetylated amino terminus (Ac-NH-), a free carboxylic acid (-COOH), and a para-brominated aromatic ring that provides a halogen-functional handle for further derivatization while maintaining the overall amino acid scaffold. As an amino acid derivative rather than a free amino acid, it is used in peptide-related intermediate preparation, structure-activity and labeling studies, and synthetic routes that require a protected/blocked amino group alongside a reactive carboxyl group for controlled coupling chemistry.
CAT No: CP26932
CAS No:273730-59-9
Synonyms/Alias:AC-P-BROMO-DL-PHE-OH;Acetyl-4-bromo-DL-phenylalanine;273730-59-9;N-Acetyl-4-bromo-L-phenylalanine;(S)-N-acetyl-4-bromophenylalanine;AC1NQASZ;SCHEMBL502447;CHEMBL1221785;CTK8E5615;LDCUXIARELPUCD-UHFFFAOYSA-N;MolPort-008-701-072;AKOS009157806;OR251461;RT-011178;2-acetamido-3-(4-bromophenyl)propanoicacid;K-6968;alpha-(Acetylamino)-4-bromobenzenepropanoicacid
Ac-p-bromo-DL-Phe-OH is an N-acetylated, para-brominated phenylalanine derivative supplied as a DL mixture, combining an aromatic side chain bearing a para-bromo substituent with a free carboxylic acid for downstream functionalization. The N-acetyl (Ac-) group reduces backbone nucleophilicity, making the compound a practical electrophile-bearing amino acid building block for assembling brominated aromatic motifs and for preparing peptide-related intermediates where controlled aromatic substitution is required. Researchers commonly select this specific substitution pattern to enable further coupling or derivatization at the aryl bromide while retaining a handle for standard amino acid intermediate workflows.
1. Aromatic Bromide Derivatization
Ac-p-bromo-DL-Phe-OH is used as a brominated amino acid building block for introducing a para-bromo phenyl motif into larger organic frameworks via aryl-bromide functionalization strategies. Medicinal chemistry and chemical biology groups often incorporate such aryl halide functionality as a synthetic handle to access substituted analogs in SAR studies, where the bromo substituent provides a convenient entry point to diversify aromatic substitution patterns while preserving the amino acid-derived backbone element for later coupling.
2. Peptide Intermediate Building Block
Ac-p-bromo-DL-Phe-OH supports the preparation of brominated peptide fragments and peptide-related intermediates in custom peptide synthesis workflows. Peptide chemistry teams use N-acetylated amino acid derivatives like this one to control reactivity during fragment assembly and to maintain an amino acid-derived structural element that can be carried into subsequent coupling steps, particularly when the para-brominated aromatic ring is needed as a later derivatization site or as part of a defined aromatic environment in the target peptide scaffold.
3. Pharmaceutical SAR Intermediate Synthesis
Ac-p-bromo-DL-Phe-OH is frequently selected for pharmaceutical intermediate development where an aryl-bromide-containing amino acid scaffold is required to generate libraries of substituted derivatives. Process and R&D chemists value the combination of a free carboxylic acid and a para-brominated aromatic ring because it enables a straightforward transition from amino acid-derived intermediates to diversified aromatic analogs, supporting iterative structure-activity relationship workflows that rely on consistent substitution patterns across analog series.
4. Analytical Reference Material Preparation
Ac-p-bromo-DL-Phe-OH can be used to prepare defined brominated amino acid standards and reference materials for method development and characterization in analytical chemistry. LC-MS and related workflows benefit from having a structurally defined, halogenated amino acid derivative with a known substitution pattern, enabling researchers to validate chromatographic behavior, confirm identity through mass-based detection, and support impurity profiling for brominated amino acid intermediates and peptide-derived analytes.
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