Cas no 181148-01-6 (4-Maleimidobutyric acid hydrazide)

4-Maleimidobutyric acid hydrazide is a heterobifunctional crosslinking reagent featuring a maleimide group and a hydrazide moiety. The maleimide group selectively reacts with thiols (e.g., cysteine residues) under mild conditions, while the hydrazide functionality enables conjugation with aldehydes or ketones, such as oxidized carbohydrates or glycoproteins. This compound is particularly useful for site-specific protein labeling, antibody-drug conjugate (ADC) development, and bioconjugation applications. Its spacer arm (butyric acid) provides sufficient length to minimize steric hindrance. The reagent is water-soluble and suitable for pH 6.5–7.5 reactions, ensuring compatibility with biological systems. Its stability and selectivity make it a valuable tool for controlled biomolecular modifications.
4-Maleimidobutyric acid hydrazide structure
181148-01-6 structure
Product Name:4-Maleimidobutyric acid hydrazide
CAS No:181148-01-6
MF:C8H11N3O3
MW:197.191241502762
MDL:MFCD11519205
CID:105578
PubChem ID:53249370
Update Time:2025-11-02

4-Maleimidobutyric acid hydrazide Chemical and Physical Properties

Names and Identifiers

    • 4-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)butanehydrazide
    • 4-Maleimidobutyric acid hydrazide
    • 4-Maleimidobutyric?Acid?hydrazide(GMBH)
    • 4-Maleimidobutyricacidhtdrazide
    • AG-E-31239
    • ANW-50112
    • CTK4D7816
    • MolPort-019-904-051
    • PubChem11843
    • QC-511
    • RB3011
    • 2,5-Dihydro-2,5-dioxo-1H-pyrrole-1-butanoic acid hydrazide
    • 4-MaleiMidobutyric acid htdrazide
    • 181148-01-6
    • AS-54418
    • A4016
    • 4-Maleimidobutyric?acid?hydrazide
    • FT-0604087
    • 4-(2,5-Dioxo-2h-pyrrol-1(5h)-yl)butanehydrazide
    • 4-(2,5-dioxopyrrol-1-yl)butanehydrazide
    • SCHEMBL13224224
    • AM62687
    • AKOS006325575
    • 1H-Pyrrole-1-butanoic acid, 2,5-dihydro-2,5-dioxo-, hydrazide
    • 4-MALEIMIDOBUTYRC ACID HYDRAZIDE
    • DTXSID50692939
    • CS-0448512
    • 4-MALEIMIDOBUTYRIC ACIDHYDRAZIDE
    • DB-003496
    • MDL: MFCD11519205
    • Inchi: 1S/C8H11N3O3/c9-10-6(12)2-1-5-11-7(13)3-4-8(11)14/h3-4H,1-2,5,9H2,(H,10,12)
    • InChI Key: BMFQKRITGGSIAB-UHFFFAOYSA-N
    • SMILES: O=C1C=CC(N1CCCC(NN)=O)=O

Computed Properties

  • Exact Mass: 197.08
  • Monoisotopic Mass: 197.08
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 6
  • Heavy Atom Count: 14
  • Rotatable Bond Count: 5
  • Complexity: 280
  • 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: _0.6
  • Topological Polar Surface Area: 92.5A^2

Experimental Properties

  • Density: 1.348±0.06 g/cm3 (20 oC 760 Torr),
  • Boiling Point: 472.2℃ at 760 mmHg
  • Flash Point: 239.398 °C
  • Solubility: Slightly soluble (24 g/l) (25 o C),
  • PSA: 92.50000
  • LogP: -0.28940

4-Maleimidobutyric acid hydrazide Security Information

4-Maleimidobutyric acid hydrazide Pricemore >>

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Additional information on 4-Maleimidobutyric acid hydrazide

4-Maleimidobutyric Acid Hydrazide (CAS No. 181148-01-6): A Versatile Bioconjugation Reagent for Cutting-Edge Research

In the rapidly evolving field of bioconjugation chemistry, 4-Maleimidobutyric acid hydrazide (CAS No. 181148-01-6) has emerged as a crucial tool for researchers working on protein modification, antibody-drug conjugates (ADCs), and targeted drug delivery systems. This heterobifunctional crosslinker combines the specificity of maleimide chemistry with the versatility of hydrazide functional groups, making it indispensable for creating stable bioconjugates under physiological conditions.

The molecular structure of 4-Maleimidobutyric acid hydrazide features two reactive moieties: a maleimide group that selectively reacts with thiol groups (-SH) at neutral pH, and a hydrazide group that forms stable linkages with aldehydes or ketones. This unique combination addresses one of the most searched questions in bioconjugation research: "How to create stable protein-protein or protein-small molecule conjugates?" The butyric acid spacer provides optimal distance between reactive groups, reducing steric hindrance in complex biological systems.

Recent advancements in ADC development have significantly increased the demand for 4-Maleimidobutyric acid hydrazide, as evidenced by growing search trends for "bioconjugation reagents for antibody-drug conjugates." The compound's ability to form stable thioether bonds with cysteine residues in antibodies while simultaneously conjugating with carbonyl-containing drug molecules makes it ideal for creating next-generation targeted therapies. Researchers particularly value its water solubility and the controlled reactivity profile that prevents unwanted polymerization.

In diagnostic applications, 4-Maleimidobutyric acid hydrazide CAS 181148-01-6 enables the development of sensitive detection systems. A frequently searched application is "fluorescent labeling of antibodies for imaging," where this reagent serves as a bridge between targeting antibodies and various reporter molecules. The hydrazide moiety can react with periodate-oxidized carbohydrate groups on antibodies, while the maleimide end conjugates with thiol-containing fluorophores, creating highly specific detection probes.

The stability profile of maleimidobutyric hydrazide derivatives has become a hot topic in pharmaceutical forums, with many researchers investigating "how to improve conjugate serum stability." Unlike some maleimide derivatives that undergo retro-Michael reactions, conjugates formed with 4-Maleimidobutyric acid hydrazide demonstrate remarkable stability in biological fluids, addressing a critical challenge in drug delivery system development.

Material science applications have also benefited from this compound, particularly in creating smart polymer conjugates. Search analytics show growing interest in "stimuli-responsive biomaterials," where 4-Maleimidobutyric acid hydrazide facilitates the incorporation of both targeting and responsive elements into polymer backbones. The reagent's ability to conjugate with multiple functional groups enables the design of complex, multifunctional materials for tissue engineering and controlled release applications.

Quality control aspects of 4-Maleimidobutyric acid hydrazide 181148-01-6 frequently appear in scientific discussions, particularly regarding "HPLC purity standards for bioconjugation reagents." High-purity grades of this compound typically show >95% purity by HPLC, with strict controls on moisture content to prevent hydrolysis of the maleimide group during storage. These specifications are crucial for reproducible results in sensitive biological applications.

The synthesis and scale-up of maleimidobutyric hydrazide compounds represent another area of active research, with many investigators searching for "cost-effective bioconjugation linker synthesis." While proprietary details vary among manufacturers, most synthetic routes involve the stepwise modification of maleic anhydride derivatives, followed by careful hydrazide incorporation to preserve the reactivity of both functional groups.

In the context of emerging technologies, 4-Maleimidobutyric acid hydrazide plays a significant role in nanoparticle functionalization, a topic showing exponential growth in search volume. Researchers working on "targeted nanomedicine platforms" utilize this reagent to attach both targeting ligands and therapeutic payloads to nanoparticle surfaces, creating sophisticated delivery systems with precise tissue specificity.

Storage and handling recommendations for CAS 181148-01-6 frequently appear in technical queries. Best practices include storage at -20°C under inert atmosphere to prevent moisture absorption and maleimide group hydrolysis. The compound's stability in various buffers is another common search topic, with most protocols recommending immediate use after dissolution in aqueous solutions to maximize conjugation efficiency.

The future outlook for 4-Maleimidobutyric acid hydrazide applications appears exceptionally bright, particularly in personalized medicine approaches. Emerging search trends indicate growing interest in "patient-specific bioconjugates" and "modular therapeutic platforms," where this versatile reagent enables rapid assembly of customized therapeutic molecules tailored to individual patient biomarkers.

As research continues to reveal new applications for maleimide-hydrazide bifunctional linkers, 4-Maleimidobutyric acid hydrazide maintains its position as a fundamental tool in the bioconjugation toolbox. Its balanced reactivity, commercial availability, and proven performance in diverse biological systems ensure its continued importance in advancing both basic research and therapeutic development across multiple disciplines.

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