Cas no 17057-04-4 (4-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)benzoic acid)

4-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)benzoic acid is a heterobifunctional crosslinking agent featuring both a maleimide and a carboxyl group. The maleimide moiety selectively reacts with thiol groups under mild conditions, while the carboxylic acid allows further conjugation via amine coupling using carbodiimide chemistry. This compound is particularly useful in bioconjugation applications, enabling the stable attachment of biomolecules such as peptides, proteins, or antibodies. Its aromatic structure enhances stability, and the spacer between functional groups minimizes steric hindrance. The product is suitable for applications in drug delivery, diagnostics, and surface functionalization, offering high specificity and efficiency in crosslinking reactions.
4-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)benzoic acid structure
17057-04-4 structure
Product Name:4-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)benzoic acid
CAS No:17057-04-4
MF:C11H7NO4
MW:217.177582979202
MDL:MFCD00458571
CID:50636
PubChem ID:86925
Update Time:2025-06-08

4-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)benzoic acid Chemical and Physical Properties

Names and Identifiers

    • 4-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)benzoic acid
    • 4-(2,5-dihydro-2,5-dioxo-1Hpyrrol-1yl)-benzoic acid
    • 4-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)-benzoic acid
    • 4-Maleimidobenzoic acid
    • 4-(N-Maleimido)benzoic acid
    • INCA-12
    • AKOS B006486
    • AKOS MSC-0031
    • ART-CHEM-BB B006486
    • N-(4-Benzoic acid)maleimide
    • N-(4-CARBOXYPHENYL)MALEIMIDE
    • 4-(2,5-Dioxo-1-pyrrolyl)benzoic acid
    • 4-(2,5-Dioxo-1H-pyrrole-1-yl)benzoic acid
    • 4-(2,5-dioxopyrrol-1-yl)benzoic acid
    • 4-(2,5-dioxo-2,5-dihydropyrrol-1-yl)benzoic acid
    • p-Maleimidobenzoic acid
    • Benzoic acid, 4-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)-
    • N-(p-Carboxyphenyl)maleimide
    • 4-(2,5-Dioxo-2,5-dihydro-pyrrol-1-yl)-benzoic acid
    • N-(4-Carboxy)Phenylmaleimide
    • 4-(2,5-DIOXO-2,5-DIHYDRO-PYRROL-1-YL)-BENZOICACID
    • LKUO
    • N- p-carboxyl phenylmaleimide
    • CBDivE_005991
    • NSC14889
    • M3257
    • EINECS 241-117-9
    • UNII-79D4NT6S3E
    • N-(para-carboxyphenyl) maleimide
    • 2-Amino-N-ethylbenzothioamide
    • EN300-09658
    • SR-01000081632
    • Z56347034
    • NSC-14889
    • Benzoic acid, p-maleimido-
    • SCHEMBL235166
    • 4-(2,5-Dihydro-2,5-dioxo-1H-pyrrol-1-yl)benzoic acid
    • AMY477
    • AS-31780
    • SY101256
    • 4-(2,5-Dioxo-2,5-dihydro-1-pyrrolyl)benzoic Acid
    • 4-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-benzoic acid, AldrichCPR
    • NS00025587
    • NSC521355
    • N-(4-carboxy phenyl) maleimide
    • J-010630
    • F0017-2366
    • EU-0040168
    • p-Carboxyphenylmaleimide
    • CHEMBL169518
    • F1265-0503
    • N-(p-carboxyphenyl) maleimide
    • BDBM155509
    • FT-0604072
    • CS-0157490
    • US9011882, Table 1, Compound 2
    • BB 0218877
    • NSC 521355
    • BP-23770
    • 4-(2,5-dioxoazolinyl)benzoic acid
    • N-(para-carboxyphenyl)maleimide
    • NSC-521355
    • DTXSID50168881
    • HY-W104848
    • 79D4NT6S3E
    • CCG-17662
    • A3763
    • MFCD00458571
    • p-(N-Maleimido)benzoic acid
    • NSC 14889
    • AKOS000118546
    • 17057-04-4
    • 4-maleimido-benzoic acid
    • SR-01000081632-1
    • AB00074231-01
    • STK298826
    • BBL010514
    • ALBB-005271
    • DB-064786
    • MDL: MFCD00458571
    • Inchi: 1S/C11H7NO4/c13-9-5-6-10(14)12(9)8-3-1-7(2-4-8)11(15)16/h1-6H,(H,15,16)
    • InChI Key: LKUOJDGRNKVVFF-UHFFFAOYSA-N
    • SMILES: O=C1C=CC(N1C1C=CC(C(=O)O)=CC=1)=O

Computed Properties

  • Exact Mass: 217.03800
  • Monoisotopic Mass: 217.038
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 16
  • Rotatable Bond Count: 2
  • Complexity: 348
  • 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: nothing
  • XLogP3: 0.6
  • Topological Polar Surface Area: 74.7

Experimental Properties

  • Density: 1.521
  • Melting Point: Not available
  • Boiling Point: 447.1°C at 760 mmHg
  • Flash Point: 224.2°C
  • PSA: 74.68000
  • LogP: 0.87920
  • Vapor Pressure: Not available

4-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)benzoic acid Security Information

  • Signal Word:Warning
  • Hazard Statement: H302-H319
  • Warning Statement: P305+P351+P338
  • Hazard Category Code: 36
  • Safety Instruction: 26
  • Hazardous Material Identification: Xi
  • HazardClass:IRRITANT
  • Storage Condition:Sealed in dry,Room Temperature

4-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)benzoic acid Customs Data

  • HS CODE:2925190090
  • Customs Data:

    China Customs Code:

    2925190090

    Overview:

    2925190090 Other imides and their derivative salts. VAT:17.0% Tax refund rate:9.0% Regulatory conditions:nothing MFN tariff:6.5% general tariff:30.0%

    Declaration elements:

    Product Name, component content, use to

    Summary:

    2925190090 other imides and their derivatives; salts thereof VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:30.0%

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4-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)benzoic acid Related Literature

Additional information on 4-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)benzoic acid

Comprehensive Overview of 4-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)benzoic acid (CAS No. 17057-04-4)

4-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)benzoic acid, identified by its CAS number 17057-04-4, is a specialized organic compound widely utilized in pharmaceutical research, material science, and bioconjugation applications. This compound features a unique molecular structure combining a benzoic acid moiety with a maleimide group, making it highly reactive and versatile for cross-linking and conjugation purposes. Researchers and industries value its role in developing targeted drug delivery systems, advanced polymers, and biofunctional materials.

The growing interest in maleimide-functionalized compounds like 4-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)benzoic acid is driven by their ability to form stable thioether bonds with thiol-containing biomolecules, such as cysteine residues in proteins. This property is critical in antibody-drug conjugates (ADCs), a hot topic in oncology research. With the rise of personalized medicine, the demand for precise bioconjugation tools has surged, positioning this compound as a key enabler in next-generation therapeutics.

From an industrial perspective, CAS 17057-04-4 is often searched alongside terms like "maleimide crosslinker", "bioconjugation reagents", and "carboxylic acid functionalized maleimides". These keywords reflect its applications in protein labeling, surface modification, and polymer chemistry. Recent advancements in nanotechnology have further expanded its use in creating functionalized nanoparticles for diagnostic and therapeutic purposes, aligning with trends in nanomedicine and smart materials.

Quality and purity are paramount for 4-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)benzoic acid, especially in pharmaceutical-grade applications. Analytical techniques such as HPLC, NMR, and mass spectrometry are routinely employed to verify its structural integrity. Suppliers often highlight its solubility profile (e.g., in DMSO or DMF) and stability under various pH conditions, addressing common queries from researchers optimizing reaction conditions.

Environmental and safety considerations are also frequently discussed in relation to CAS 17057-04-4. While not classified as hazardous, proper handling protocols are recommended to avoid decomposition at high temperatures. The compound’s biodegradability and eco-friendly disposal methods are increasingly relevant topics, reflecting the broader shift toward sustainable chemistry practices.

In summary, 4-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)benzoic acid (17057-04-4) bridges multiple cutting-edge fields, from drug development to advanced material engineering. Its adaptability to emerging technologies ensures continued relevance in both academic and industrial settings, making it a compound of significant scientific and commercial interest.

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