Cas no 32116-25-9 (2-Acetyl-5-nitropyrrole)

2-Acetyl-5-nitropyrrole is a nitrated pyrrole derivative characterized by the presence of an acetyl group at the 2-position and a nitro group at the 5-position. This compound serves as a versatile intermediate in organic synthesis, particularly in the preparation of heterocyclic compounds and pharmaceutical building blocks. Its electron-withdrawing nitro group enhances reactivity in nucleophilic substitution and reduction reactions, while the acetyl moiety offers functionalization opportunities. The compound’s well-defined structure and stability under controlled conditions make it suitable for applications in medicinal chemistry and materials science. It is typically handled under inert conditions due to its sensitivity to light and moisture.
2-Acetyl-5-nitropyrrole structure
2-Acetyl-5-nitropyrrole structure
Product Name:2-Acetyl-5-nitropyrrole
CAS No:32116-25-9
MF:C6H6N2O3
MW:154.12344121933
CID:310741
PubChem ID:36066
Update Time:2025-06-08

2-Acetyl-5-nitropyrrole Chemical and Physical Properties

Names and Identifiers

    • Ethanone,1-(5-nitro-1H-pyrrol-2-yl)-
    • 2-Acetyl-5-nitropyrrole
    • 1-(5-nitro-1H-pyrrol-2-yl)ethanone
    • Ketone, methyl 5-nitropyrrol-2-yl
    • KETONE, METHYL (5-NITRO-2-PYRROLYL)
    • U66Y4C4WEY
    • NSC-87231
    • 1-(5-nitro-1H-pyrrol-2-yl)ethan-1-one
    • Ethanone, 1-(5-nitro-1H-pyrrol-2-yl)-
    • Pyrrole, 2-acetyl-5-nitro-
    • UNII-U66Y4C4WEY
    • NSC87231
    • DTXSID80185905
    • NSC 87231
    • FT-0708291
    • ACETYL-5-NITROPYRROLE, 2-
    • 32116-25-9
    • BRN 0130864
    • 2-Nitro-5-acetyl-1H-pyrrole
    • 5-nitro-2-acetylpyrrole
    • Inchi: 1S/C6H6N2O3/c1-4(9)5-2-3-6(7-5)8(10)11/h2-3,7H,1H3
    • InChI Key: LIJJWPMRFYFJFR-UHFFFAOYSA-N
    • SMILES: O=C(C)C1=CC=C([N+](=O)[O-])N1

Computed Properties

  • Exact Mass: 154.03788
  • Monoisotopic Mass: 154.03784206g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 1
  • Complexity: 187
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 0.9
  • Topological Polar Surface Area: 78.7?2

Experimental Properties

  • Density: 1.4564 (rough estimate)
  • Boiling Point: 277.46°C (rough estimate)
  • Refractive Index: 1.5100 (estimate)
  • PSA: 76

2-Acetyl-5-nitropyrrole Pricemore >>

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Additional information on 2-Acetyl-5-nitropyrrole

Introduction to 2-Acetyl-5-nitropyrrole (CAS No. 32116-25-9)

2-Acetyl-5-nitropyrrole, with the chemical formula C?H?N?O?, is a heterocyclic compound that has garnered significant attention in the field of pharmaceutical chemistry and materials science due to its versatile structural framework and potential biological activities. This compound belongs to the pyrrole derivatives family, which is well-known for its role in various synthetic pathways and medicinal applications. The presence of both acetyl and nitro functional groups in its molecular structure imparts unique reactivity, making it a valuable intermediate in the synthesis of more complex molecules.

The CAS number 32116-25-9 uniquely identifies this compound in scientific literature and industrial applications, ensuring precise referencing and consistency across different research groups and manufacturing processes. The nitro group, specifically located at the 5-position of the pyrrole ring, is a key feature that influences the electronic properties of the molecule. This substitution pattern enhances its utility as a building block in organic synthesis, particularly in the development of pharmaceuticals and agrochemicals.

In recent years, 2-Acetyl-5-nitropyrrole has been explored for its potential applications in medicinal chemistry. The acetyl group at the 2-position can be readily modified through various chemical reactions, such as condensation, alkylation, or acylation, which opens up numerous possibilities for designing novel bioactive compounds. Researchers have been particularly interested in its role as a precursor for antimalarial and anticancer agents. For instance, modifications of the nitro group to amine or hydroxyl derivatives have shown promise in inhibiting certain enzymes involved in pathogenic processes.

One of the most compelling aspects of 2-Acetyl-5-nitropyrrole is its ability to serve as a scaffold for drug discovery. The pyrrole core is a common motif in many biologically active molecules, including heme-binding agents and antiviral drugs. By leveraging the reactivity of both functional groups, chemists can design molecules with tailored properties for specific therapeutic targets. For example, recent studies have demonstrated that derivatives of this compound exhibit inhibitory effects on certain bacterial enzymes by disrupting their active sites.

The synthesis of 2-Acetyl-5-nitropyrrole typically involves multi-step organic reactions starting from commercially available pyrrole derivatives. The introduction of the nitro group is often achieved through electrophilic aromatic substitution, while the acetyl group is introduced via acylation reactions. These synthetic routes have been optimized to ensure high yields and purity, making the compound accessible for further functionalization and application development.

From a materials science perspective, 2-Acetyl-5-nitropyrrole has also shown potential in the development of advanced materials. Its aromatic structure and electron-withdrawing nature make it suitable for use in organic electronics, such as light-emitting diodes (OLEDs) and conductive polymers. Researchers are investigating its incorporation into π-conjugated systems to enhance charge transport properties, which could lead to more efficient electronic devices.

The growing interest in 2-Acetyl-5-nitropyrrole has spurred further research into its derivatives and analogs. Computational studies have been employed to predict the biological activity of various modifications, guiding experimental efforts towards more effective candidates. Additionally, green chemistry principles are being applied to develop more sustainable synthetic routes, reducing waste and energy consumption without compromising yield or quality.

In conclusion, 2-Acetyl-5-nitropyrrole (CAS No. 32116-25-9) is a multifaceted compound with significant potential in pharmaceuticals and materials science. Its unique structural features enable diverse applications, from drug development to advanced materials engineering. As research continues to uncover new possibilities for this molecule and its derivatives, it is likely to remain a cornerstone in synthetic chemistry for years to come.

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