5-Br-IAA is a halogenated indole-3-acetic acid (IAA) derivative in which a bromine substituent is present on the indole ring, retaining the carboxylic acid side chain characteristic of this amino-acid-like scaffold. The molecule contains a free carboxyl group and an indole nitrogen within the aromatic system, and its substitution pattern provides a defined site for chemical reactivity and spectroscopic differentiation relative to unsubstituted IAA. 5-Br-IAA is used in chemical biology and analytical method development as a labeled or structurally modified auxin-like probe for studying structure-property relationships, supporting synthesis of further indole-based derivatives, and enabling bromine-dependent detection or conjugation strategies.
CAT No: CP25836
CAS No:40432-84-6
Synonyms/Alias:5-Bromoindole-3-aceticacid;40432-84-6;2-(5-bromo-1H-indol-3-yl)aceticacid;(5-Bromo-1H-indol-3-yl)-aceticacid;(5-bromo-1H-indol-3-yl)aceticacid;CHEMBL82440;1h-indole-3-aceticacid,5-bromo-;MFCD00005637;SBB066626;5-BROMO-1H-INDOLE-3-ACETICACID;2-(5-bromoindol-3-yl)aceticacid;4ojq;NSC88145;PubChem15852;ACMC-1AO2Y;5-BR-IAA;5-Bromoindole-3aceticacid;AC1L3X3R;AC1Q1H9S;5-Bromo-3-indoleaceticacid;B68720_ALDRICH;5-bromo-3-indolylaceticacid;KSC237Q3N;SCHEMBL1519655;CTK1D7836
5-Br-IAA is a halogenated indole-3-acetic acid (IAA) derivative bearing a bromine substituent, retaining the indole acetic acid scaffold while modifying the aromatic ring electronics and mass. Researchers use this compound as a stable, structurally defined auxin analog for probing auxin-responsive chemistry and for building labeled or derivatized indoleacetic acid reagents where a brominated handle improves analytical detectability and downstream functionalization options. In chemical biology and plant hormone research workflows, the 5-bromo substitution supports comparative studies against IAA and enables preparation of brominated intermediates for further synthetic and conjugation steps.
1. Auxin Analog Studies
5-Br-IAA is used in chemical biology and plant hormone research to create controlled comparisons with indole-3-acetic acid analogs when evaluating auxin-responsive pathways and auxin-dependent chemical reactivity in vitro. Laboratories performing structure-activity relationship experiments rely on this defined halogenated scaffold to assess how aromatic substitution influences auxin-like behavior in binding, uptake-mimicking assays, and downstream reporter readouts. Because the compound is a discrete small-molecule auxin analog rather than a complex extract, it supports reproducible experimental design for mechanistic probing and reagent standardization across experiments.
2. Indoleacetic Acid Derivatization
5-Br-IAA serves as a practical starting material for preparing brominated indoleacetic acid derivatives used in medicinal chemistry and specialized probe development. Synthetic teams incorporate the brominated aromatic position to access further functionalization strategies that generate analog libraries for SAR work, including electrophile-compatible downstream transformations and derivatization routes that preserve the indole acetic acid motif. This makes the compound valuable in workflows where a halogenated auxin scaffold is required to tune physicochemical properties, introduce new substituents, or generate intermediates for subsequent conjugation to larger reporter systems.
3. Analytical Reference And LC-MS Workflows
5-Br-IAA is frequently employed as an analytical reference compound for method development and calibration in LC-MS-based quantification of indoleacetic acid analogs and related auxin chemistry. Bromination provides a distinct mass signature and improved differentiation from non-halogenated IAA in complex matrices, which supports more reliable identification during chromatographic screening and confirmatory analysis. Analytical chemistry groups use the compound to support internal method robustness when monitoring auxin analog stability, degradation products, or derivatized forms generated during sample preparation.
4. Probe And Tag Intermediate Development
5-Br-IAA is leveraged as a structurally defined intermediate for constructing auxin-inspired chemical probes and tagged reagents used to study auxin-associated processes at the molecular level. Chemical biology groups select this brominated scaffold when they need a consistent indoleacetic acid core while adding a functional handle for downstream attachment to detection moieties, affinity tags, or imaging-compatible fragments. In these workflows, the brominated aromatic ring helps maintain the auxin-like backbone while enabling controlled probe synthesis, supporting reproducible reagent generation for binding studies, pull-down experiments, or traceable analog tracking in experimental systems.
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