Cas no 5408-07-1 (Ethyl 4-bromo-3,5-dimethyl-1H-pyrrole-2-carboxylate)

Ethyl 4-bromo-3,5-dimethyl-1H-pyrrole-2-carboxylate is a brominated pyrrole derivative with a molecular formula of C9H12BrNO2. This compound serves as a versatile intermediate in organic synthesis, particularly in the preparation of pharmaceuticals, agrochemicals, and functional materials. The presence of both bromine and ester functional groups enhances its reactivity, enabling selective cross-coupling reactions and further derivatization. Its stable crystalline form ensures ease of handling and storage. The 3,5-dimethyl substitution pattern contributes to steric control in reactions, improving regioselectivity. This compound is valued for its role in constructing complex heterocyclic frameworks, making it a useful building block in medicinal chemistry and material science research.
Ethyl 4-bromo-3,5-dimethyl-1H-pyrrole-2-carboxylate structure
5408-07-1 structure
Product Name:Ethyl 4-bromo-3,5-dimethyl-1H-pyrrole-2-carboxylate
CAS No:5408-07-1
MF:C9H12BrNO2
MW:246.101081848145
MDL:MFCD02647051
CID:1003952
PubChem ID:138486
Update Time:2025-06-08

Ethyl 4-bromo-3,5-dimethyl-1H-pyrrole-2-carboxylate Chemical and Physical Properties

Names and Identifiers

    • ETHYL 4-BROMO-3,5-DIMETHYL-1H-PYRROLE-2-CARBOXYLATE
    • Pyrrole-2-carboxylic acid, 4-bromo-3,5-dimethyl-, ethyl ester
    • 1H-Pyrrole-2-carboxylic acid,4-bromo-3,5-dimethyl-,ethyl ester
    • 2,4-dimethyl-3-bromo-5-carbethoxy pyrrole
    • 4-Brom-3,5-dimethyl-pyrrol-2-carbonsaeure-aethylester
    • 4-bromo-2-ethoxycarbonyl-3,5-dimethylpyrrole
    • 4-bromo-3,5-dimethyl-1H-pyrrole-2-carboxylic acid ethyl ester
    • 4-bromo-3,5-dimethyl-pyrrole-2-carboxylic acid ethyl ester
    • ethyl 4-bromo-3,5-dimethylpyrrole-2-carboxylate
    • 1H-Pyrrole-2-carboxylic acid, 4-bromo-3,5-dimethyl-, ethyl ester
    • NSC10761
    • POLBZQUAKJYNIF-UHFFFAOYSA-N
    • SBB053895
    • RP06010
    • NE40147
    • Y9398
    • ST50949734
    • MFCD02647051
    • SR-01000530519
    • CS-B1574
    • C13504
    • SY143684
    • DB-010894
    • Ethyl 4-bromo-3,5-dimethyl-1H-pyrrole-2-carboxylate, AldrichCPR
    • EN300-119447
    • W-204292
    • DTXSID20202408
    • J-520975
    • TS-03392
    • Z1269130196
    • AKOS015899109
    • NSC 10761
    • SB62088
    • SCHEMBL2026881
    • NSC-10761
    • 5408-07-1
    • SR-01000530519-1
    • 1H-Pyrrole-2-carboxylic acid, 4-bromo-3,5-dimethyl,ethyl ester
    • AG-205/13360146
    • Ethyl 4-bromo-3,5-dimethyl-1H-pyrrole-2-carboxylate
    • MDL: MFCD02647051
    • Inchi: 1S/C9H12BrNO2/c1-4-13-9(12)8-5(2)7(10)6(3)11-8/h11H,4H2,1-3H3
    • InChI Key: POLBZQUAKJYNIF-UHFFFAOYSA-N
    • SMILES: BrC1=C(C)NC(C(=O)OCC)=C1C

Computed Properties

  • Exact Mass: 245.00500
  • Monoisotopic Mass: 245.00514g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 3
  • Complexity: 198
  • 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
  • Topological Polar Surface Area: 42.1
  • XLogP3: 2.7

Experimental Properties

  • PSA: 42.09000
  • LogP: 2.57070

Ethyl 4-bromo-3,5-dimethyl-1H-pyrrole-2-carboxylate Customs Data

  • HS CODE:2933990090
  • Customs Data:

    China Customs Code:

    2933990090

    Overview:

    2933990090. Other heterocyclic compounds containing only nitrogen heteroatoms. VAT:17.0%. Tax refund rate:13.0%. Regulatory conditions:nothing. MFN tariff:6.5%. general tariff:20.0%

    Declaration elements:

    Product Name, component content, use to, Please indicate the appearance of Urotropine, 6- caprolactam please indicate the appearance, Signing date

    Summary:

    2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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Additional information on Ethyl 4-bromo-3,5-dimethyl-1H-pyrrole-2-carboxylate

Recent Advances in the Application of Ethyl 4-bromo-3,5-dimethyl-1H-pyrrole-2-carboxylate (CAS: 5408-07-1) in Chemical Biology and Pharmaceutical Research

Ethyl 4-bromo-3,5-dimethyl-1H-pyrrole-2-carboxylate (CAS: 5408-07-1) is a brominated pyrrole derivative that has garnered significant attention in recent years due to its versatile applications in chemical biology and pharmaceutical research. This compound serves as a key intermediate in the synthesis of various biologically active molecules, including potential drug candidates. Recent studies have explored its utility in medicinal chemistry, particularly in the development of novel therapeutic agents targeting infectious diseases, cancer, and inflammatory disorders.

One of the most notable advancements involving Ethyl 4-bromo-3,5-dimethyl-1H-pyrrole-2-carboxylate is its role in the synthesis of pyrrole-based scaffolds for drug discovery. Researchers have utilized this compound to develop inhibitors of specific enzymes and receptors, such as kinase inhibitors and G-protein-coupled receptor (GPCR) modulators. For instance, a 2023 study published in the Journal of Medicinal Chemistry demonstrated the compound's efficacy in the synthesis of selective kinase inhibitors with potential applications in oncology. The study highlighted the compound's ability to introduce bromine at the 4-position, which is critical for enhancing binding affinity and selectivity.

In addition to its role in drug discovery, Ethyl 4-bromo-3,5-dimethyl-1H-pyrrole-2-carboxylate has been investigated for its antimicrobial properties. A recent study in Bioorganic & Medicinal Chemistry Letters (2024) reported that derivatives of this compound exhibited potent activity against multidrug-resistant bacterial strains, including methicillin-resistant Staphylococcus aureus (MRSA). The researchers attributed this activity to the bromine substituent, which enhances the compound's interaction with bacterial cell membranes and intracellular targets.

Another emerging application of Ethyl 4-bromo-3,5-dimethyl-1H-pyrrole-2-carboxylate is in the field of chemical biology, where it is used as a building block for the development of fluorescent probes and imaging agents. A 2024 study in Chemical Communications described the synthesis of a pyrrole-based fluorescent probe derived from this compound, which was used to visualize reactive oxygen species (ROS) in live cells. This innovation opens new avenues for studying oxidative stress-related diseases, such as neurodegenerative disorders and cancer.

Despite its promising applications, challenges remain in the large-scale synthesis and optimization of Ethyl 4-bromo-3,5-dimethyl-1H-pyrrole-2-carboxylate derivatives. Recent efforts have focused on improving synthetic methodologies to enhance yield and purity. For example, a 2023 publication in Organic Process Research & Development outlined a scalable and environmentally friendly synthesis route for this compound, utilizing catalytic bromination and esterification techniques.

In conclusion, Ethyl 4-bromo-3,5-dimethyl-1H-pyrrole-2-carboxylate (CAS: 5408-07-1) continues to be a valuable tool in chemical biology and pharmaceutical research. Its versatility as a synthetic intermediate, combined with its biological activity, makes it a compound of significant interest for future studies. Ongoing research is expected to further elucidate its potential in drug development and diagnostic applications, paving the way for innovative therapeutic solutions.

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