1-Acetyl-5-bromo-7-nitro-2,3-dihydro-1H-indole is a substituted indole derivative bearing a fused bicyclic heteroaromatic core with partial saturation at the 2,3-positions, along with an N-acetyl substituent. The molecule contains a bromo substituent and a nitro group on the indole ring, and the N-acetyl functionality provides an amide-type nitrogen that alters hydrogen-bonding and chemoselectivity relative to the corresponding free indole. In synthesis and chemical biology research, this halogenated and nitro-functionalized indole scaffold is used as a precursor for further functionalization through electrophilic substitution or cross-coupling at the bromo position, and as a labeled or intermediate building block for constructing more complex heteroaryl derivatives.
CAT No: CP27285
CAS No:62368-07-4
Synonyms/Alias:6234-01-1;H-Glu(OtBu)-OMe.HCl;L-Glutamicacid5-tert-butyl1-methylesterhydrochloride;(S)-5-tert-Butyl1-methyl2-aminopentanedioatehydrochloride;5-tert-Butyl1-methylL-glutamatehydrochloride;H-Glu(OtBu)-OMeinvertedexclamationmarkcurrencyHCl;H-Glu(OtBu)-OMeHCl;Glu(OtBu)-OMe.HCl;H-Glu(OtBu)-OMeCl;PubChem19039;KSC491O2T;91043_ALDRICH;H-Glu(OtBu)-OMehydrochloride;SCHEMBL1143881;Jsp000039;91043_FLUKA;CTK3J1729;MolPort-003-939-678;YIFPACFSZQWAQF-FJXQXJEOSA-N;EINECS228-348-0;ANW-14024;CH-173;AKOS016842891;RTR-037310;VA50469
1-Acetyl-5-bromo-7-nitro-2,3-dihydro-1H-indole is a halogenated, nitro-substituted indole derivative bearing an acetyl-protected nitrogen, providing a chemically stable scaffold for downstream functionalization. Its combination of an aryl bromide and a nitro group makes it a practical intermediate for medicinal chemistry and heteroaromatic building-block workflows where controlled substitution patterns are required. The partially saturated indole framework supports use as a versatile precursor in the synthesis of substituted indole-containing small molecules.
1. Pharmaceutical Scaffold Building
1-Acetyl-5-bromo-7-nitro-2,3-dihydro-1H-indole is used by medicinal chemistry teams as an intermediate for assembling substituted indole-based scaffolds, where the bromine handle enables late-stage diversification and the nitro substituent supports further derivatization to access a range of electronic and hydrogen-bonding motifs. In small-molecule discovery and lead-optimization programs, this type of functionalized indole precursor is valued for providing a defined substitution pattern early in the synthesis route, allowing rapid exploration of analog series. The acetylated indole nitrogen helps maintain a consistent reactivity profile during multi-step transformations commonly used in library synthesis.
2. Cross-Coupling Diversification
1-Acetyl-5-bromo-7-nitro-2,3-dihydro-1H-indole is routinely selected for halogen-directed coupling strategies in research and specialty chemical manufacturing, leveraging the aryl bromide as a key reactive site for carbon-carbon bond formation. This enables the introduction of diverse aryl or heteroaryl fragments onto the indole core to generate analogs for structure-activity relationship studies and scaffold expansion. The presence of the nitro group supports building-block flexibility, as it can be retained or transformed depending on the target substitution pattern required downstream.
3. Nitro-Group Functional Derivatization
1-Acetyl-5-bromo-7-nitro-2,3-dihydro-1H-indole supports synthetic routes where the nitro substituent is used as a functional handle for converting the indole derivative into alternative nitrogen- and oxygen-containing substitution patterns. In pharmaceutical intermediate development, nitro-bearing heteroaromatics are often employed to access reduced or otherwise modified derivatives that change polarity, hydrogen-bonding behavior, and overall physicochemical properties of the final compounds. The defined indole substitution pattern provided by this precursor helps streamline downstream purification and analog synthesis when multiple derivatives are prepared in parallel.
4. Specialty Heteroaromatic Intermediate
1-Acetyl-5-bromo-7-nitro-2,3-dihydro-1H-indole is applied in industrial and contract synthesis settings as a specialty heteroaromatic intermediate for custom small-molecule manufacturing. Process development groups use this scaffold to prepare defined indole-containing intermediates that can be further elaborated into final candidates, agrochemical-like heteroaromatic motifs, or other substituted aromatic frameworks used in research programs. The combination of a stable acetyl-protected nitrogen with orthogonal functional groups (bromide and nitro) supports practical downstream branching, making it a useful starting point for controlled, substitution-specific chemistry.
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