4-Nitro-2-(trichloroacetyl)-1H-pyrrole is a substituted 1H-pyrrole bearing a nitro group and a trichloroacetyl substituent, classifiable as a halogenated acylated heteroaromatic building block rather than an amino acid. The molecule contains a pyrrolic N-H (1H-pyrrole) and an electron-withdrawing nitro substituent, while the trichloroacetyl group introduces a carbonyl functionality attached to a CCl3 moiety that can participate in acyl transfer chemistry and provides strong inductive effects on the ring. In synthetic chemistry workflows, this heteroaromatic scaffold is used as a precursor for preparing more complex nitrogen-containing compounds, including functionalized pyrrole derivatives for structure-activity studies and for constructing labeled or conjugatable intermediates through the reactivity of the acyl and nitro substituents.
CAT No: CP27186
CAS No:53391-50-7
Synonyms/Alias:53391-50-7;2,2,2-trichloro-1-(4-nitro-1H-pyrrol-2-yl)-1-ethanone;2,2,2-trichloro-1-(4-nitro-1H-pyrrol-2-yl)ethanone;KD-0208;2,2,2-trichloro-1-(4-nitro-1H-pyrrol-2-yl)ethan-1-one;AC1Q1Y8J;trichloronitropyrrolylethanone;C6H3Cl3N2O3;SCHEMBL1160372;CTK4J7854;MolPort-002-469-554;XFHRTOGIBMVNEV-UHFFFAOYSA-N;ZINC2547585;5083AE;SBB101904;AKOS005073117;MCULE-6615429136;NE56566;RP14598;2,2,2-TRICHLORO-1--ETHANONE;HE014912;HE090014;TR-018886;4-NITRO-2-(TRICHLOROACETYL)-PYRROLE;FT-0681322
4-Nitro-2-(trichloroacetyl)-1H-pyrrole is a substituted pyrrole building block bearing a nitro group and an acylated nitrogen (trichloroacetyl), providing strong electron-withdrawing functionality and a reactive carbonyl handle for downstream derivatization. Its heteroaromatic core makes it useful in heterocycle-focused synthesis programs where controlled functional group placement is required, while the trichloroacetyl moiety supports transformation into more advanced intermediates for medicinal chemistry and specialty chemical manufacturing. Researchers typically select this compound when a nitro-functionalized pyrrole scaffold is needed to access further substituted analogs through selective functional group interconversions.
1. Heteroaryl Intermediate Synthesis
4-Nitro-2-(trichloroacetyl)-1H-pyrrole is used as a heteroaryl intermediate for building substituted pyrrole derivatives in small-molecule synthesis workflows. Medicinal chemistry and process chemistry teams often incorporate this scaffold to rapidly generate analog series where the nitro group and the acylated pyrrole nitrogen provide handles for subsequent functional group modification. The compound's defined substitution pattern supports structured SAR (structure-activity relationship) programs and enables access to later-stage intermediates used in the preparation of heteroaryl-containing candidates and research tool scaffolds.
2. Nitro-Functionalization Derivative Access
4-Nitro-2-(trichloroacetyl)-1H-pyrrole supports downstream chemistry that leverages the nitro group as a versatile functional handle for creating reduced, substituted, or further elaborated aromatic/heteroaryl derivatives. Synthetic chemists commonly use nitro-bearing heteroaromatics to access aniline-like or otherwise modified states that serve as entry points to additional coupling, substitution, or derivatization steps in medicinal chemistry and specialty chemical programs. In practice, this compound is selected when a nitro-functionalized pyrrole core is required as a controlled precursor for generating a set of structurally related intermediates.
3. Acyl-Mediated Scaffold Building
4-Nitro-2-(trichloroacetyl)-1H-pyrrole is frequently employed as an acylated pyrrole precursor for constructing protected or activated heteroaryl frameworks that can be carried through multi-step synthesis. The trichloroacetyl group provides a distinct carbonyl functionality that can be used to modulate reactivity and enable preparation of more elaborated pyrrole-based intermediates for downstream coupling or transformation strategies. This makes the compound valuable to teams developing heterocycle libraries, where maintaining the integrity of the pyrrole core while enabling subsequent steps is a key requirement.
4. Medicinal Chemistry Lead Optimization
4-Nitro-2-(trichloroacetyl)-1H-pyrrole is used in medicinal chemistry research as a scaffold precursor for lead optimization efforts targeting heteroaryl-containing structures. Organic synthesis groups value this type of nitro-functionalized pyrrole intermediate because it allows systematic exploration of substitution patterns and functional group conversions that can influence physicochemical properties and binding-site interactions in structure-guided programs. The compound is typically handled in synthetic route development and analog generation, supporting the creation of defined heteroaryl intermediates used to evaluate structure-activity trends during early discovery and preclinical research chemistry.
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