Cas no 46413-66-5 (3-(4-bromophenyl)-1H-pyrazole-5-carboxylic acid)

3-(4-Bromophenyl)-1H-pyrazole-5-carboxylic acid is a brominated pyrazole derivative with a carboxylic acid functional group, making it a versatile intermediate in organic synthesis and pharmaceutical research. Its structure features a 4-bromophenyl substituent, which enhances reactivity in cross-coupling reactions, such as Suzuki or Buchwald-Hartwig couplings, facilitating the construction of complex molecules. The carboxylic acid moiety allows for further derivatization, including esterification or amidation, broadening its utility in medicinal chemistry. This compound is particularly valuable in the development of bioactive molecules, serving as a scaffold for kinase inhibitors or other therapeutic agents. Its high purity and well-defined structure ensure reproducibility in research applications.
3-(4-bromophenyl)-1H-pyrazole-5-carboxylic acid structure
46413-66-5 structure
Product Name:3-(4-bromophenyl)-1H-pyrazole-5-carboxylic acid
CAS No:46413-66-5
MF:C10H7BrN2O2
MW:267.078781366348
MDL:MFCD06200702
CID:328408
PubChem ID:24882573
Update Time:2025-05-20

3-(4-bromophenyl)-1H-pyrazole-5-carboxylic acid Chemical and Physical Properties

Names and Identifiers

    • 1H-Pyrazole-3-carboxylicacid, 5-(4-bromophenyl)-
    • 3-(4-BROMOPHENYL)-1H- PYRAZOLE-5-CARBOXYLIC ACID
    • 3-(4-BROMOPHENYL)-1H-PYRAZOLE-5-CARBOXY&amp
    • 5-(4-bromo-phenyl)-1(2)H-pyrazole-3-carboxylic acid
    • 5-(4-Bromphenyl)-pyrazol-3-carboxylsaeure
    • amp
    • 3-(4-bromophenyl)-1H-pyrazole-5-carboxylic acid
    • AKOS001063499
    • BS-4864
    • 46413-66-5
    • MFCD06200702
    • 2-CHLORO-3-CYANOPYRIDIN-4-YLBORONICACID
    • 890591-20-5
    • 5-(4-BROMOPHENYL)-1H-PYRAZOLE-3-CARBOXYLIC ACID
    • SCHEMBL23803931
    • A912639
    • F3250-0623
    • 1H-Pyrazole-3-carboxylicacid,5-(4-bromophenyl)-
    • VU0607297-1
    • 5-(4-Bromo-phenyl)-2H-pyrazole-3-carboxyli c acid
    • Z56795085
    • DTXSID701008638
    • BB 0239270
    • EN300-13028
    • FT-0679248
    • SCHEMBL1413926
    • AKOS025394694
    • AB12674
    • AKOS000266377
    • 3-(4-Bromophenyl)-1H-pyrazole-5-carboxylic acid, 97%
    • ALBB-006693
    • STK501289
    • MDL: MFCD06200702
    • Inchi: 1S/C10H7BrN2O2/c11-7-3-1-6(2-4-7)8-5-9(10(14)15)13-12-8/h1-5H,(H,12,13)(H,14,15)
    • InChI Key: QEOVHDPWTQAMLB-UHFFFAOYSA-N
    • SMILES: BrC1C=CC(=CC=1)C1C=C(C(=O)O)NN=1

Computed Properties

  • Exact Mass: 265.96900
  • Monoisotopic Mass: 265.96909g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 15
  • Rotatable Bond Count: 2
  • Complexity: 242
  • 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
  • Surface Charge: 0
  • Tautomer Count: 4
  • XLogP3: 2.4
  • Topological Polar Surface Area: 66?2

Experimental Properties

  • Color/Form: solid
  • Density: 1.723
  • Melting Point: 258-262?°C (lit.)
  • Boiling Point: 535.9°Cat760mmHg
  • Flash Point: 277.9°C
  • PSA: 65.98000
  • LogP: 2.53740
  • Solubility: Not available

3-(4-bromophenyl)-1H-pyrazole-5-carboxylic acid Security Information

  • Symbol: GHS07
  • Signal Word:Warning
  • Hazard Statement: H302-H319
  • Warning Statement: P305+P351+P338
  • Hazardous Material transportation number:NONH for all modes of transport
  • WGK Germany:3
  • Hazard Category Code: 22
  • Safety Instruction: S36
  • Hazardous Material Identification: Xn
  • Risk Phrases:R22

3-(4-bromophenyl)-1H-pyrazole-5-carboxylic acid Customs Data

  • HS CODE:2933199090
  • Customs Data:

    China Customs Code:

    2933199090

    Overview:

    2933199090. Other structurally non fused pyrazole ring compounds. 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:

    2933199090. other compounds containing an unfused pyrazole ring (whether or not hydrogenated) in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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Additional information on 3-(4-bromophenyl)-1H-pyrazole-5-carboxylic acid

Introduction to 3-(4-bromophenyl)-1H-pyrazole-5-carboxylic acid (CAS No. 46413-66-5)

3-(4-bromophenyl)-1H-pyrazole-5-carboxylic acid, identified by the chemical compound code CAS No. 46413-66-5, is a significant intermediate in the field of pharmaceutical chemistry and medicinal research. This compound belongs to the pyrazole class, which has garnered considerable attention due to its diverse biological activities and structural versatility. The presence of a 4-bromophenyl substituent and a carboxylic acid functional group at the 5-position of the pyrazole ring imparts unique chemical properties that make it a valuable scaffold for drug discovery and development.

The pyrazole core is a six-membered heterocyclic aromatic ring containing two nitrogen atoms at positions 1 and 5. This structural motif is known for its ability to interact with biological targets such as enzymes and receptors, making it a privileged scaffold in medicinal chemistry. The introduction of a 4-bromophenyl group at the 3-position of the pyrazole ring enhances its reactivity and binding affinity, which can be exploited for designing novel therapeutic agents. Additionally, the carboxylic acid moiety at the 5-position provides opportunities for further functionalization, allowing chemists to tailor the compound’s properties for specific applications.

Recent advancements in synthetic chemistry have enabled more efficient and scalable methods for the preparation of 3-(4-bromophenyl)-1H-pyrazole-5-carboxylic acid. These methods often involve multi-step organic transformations, including condensation reactions, bromination, and carboxylation, which are optimized to maximize yield and purity. The compound’s stability under various reaction conditions makes it a preferred choice for researchers aiming to explore new pharmacophores.

In the realm of pharmaceutical research, 3-(4-bromophenyl)-1H-pyrazole-5-carboxylic acid has been investigated for its potential as an anti-inflammatory agent, an antioxidant, and an antimicrobial agent. The bromine atom in the 4-bromophenyl group facilitates further derivatization through cross-coupling reactions such as Suzuki-Miyaura or Buchwald-Hartwig couplings, enabling the introduction of diverse functional groups onto the pyrazole scaffold. This flexibility has led to the synthesis of numerous analogs with enhanced biological activity.

One of the most compelling aspects of 3-(4-bromophenyl)-1H-pyrazole-5-carboxylic acid is its role in developing kinase inhibitors. Kinases are enzymes that play crucial roles in cell signaling pathways, and their dysregulation is associated with various diseases, including cancer. By targeting specific kinases, small-molecule inhibitors can modulate these pathways and restore normal cellular function. The pyrazole core has been shown to bind effectively to ATP pockets in kinase active sites, making it an ideal platform for drug design. The presence of both a 4-bromophenyl group and a carboxylic acid moiety allows for precise tuning of binding interactions, enhancing selectivity and potency.

Recent studies have highlighted the potential of 3-(4-bromophenyl)-1H-pyrazole-5-carboxylic acid in addressing neurological disorders. The compound’s ability to cross the blood-brain barrier has been explored in models of neurodegenerative diseases such as Alzheimer’s and Parkinson’s disease. Researchers have synthesized derivatives of this compound that exhibit neuroprotective effects by modulating neurotransmitter release and reducing oxidative stress. The versatility of the pyrazole scaffold allows for further modifications that can fine-tune its pharmacokinetic properties, making it an attractive candidate for future clinical trials.

The synthesis and application of 3-(4-bromophenyl)-1H-pyrazole-5-carboxylic acid also intersect with materials science, particularly in the development of organic electronic materials. Pyrazole derivatives have been used in organic light-emitting diodes (OLEDs) and photovoltaic cells due to their electron-donating properties and ability to form stable radicals. The bromine substituent enhances reactivity in polymerization reactions, allowing for the creation of conjugated polymers with tunable optoelectronic properties.

In conclusion, 3-(4-bromophenyl)-1H-pyrazole-5-carboxylic acid (CAS No. 46413-66-5) is a multifaceted compound with significant potential in pharmaceuticals, materials science, and beyond. Its unique structural features—combining a pyrazole core with a 4-bromophenyl substituent and a carboxylic acid group—make it a versatile scaffold for drug discovery and material innovation. As research continues to uncover new applications for this compound, its importance in advancing scientific knowledge and technological development is likely to grow.

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