Cas no 55750-48-6 (N-(Methoxycarbonyl) Maleimide)

N-(Methoxycarbonyl) Maleimide is a versatile chemical intermediate widely used in organic synthesis and polymer chemistry. Its key advantages include high reactivity as a dienophile in Diels-Alder reactions and its ability to participate in Michael additions, making it valuable for constructing complex molecular frameworks. The methoxycarbonyl group enhances solubility in organic solvents, facilitating handling and reaction conditions. This compound is particularly useful in the modification of biomolecules and the synthesis of functional polymers, where its maleimide moiety enables selective conjugation with thiol groups. Its stability under ambient conditions and well-defined reactivity profile make it a reliable choice for research and industrial applications.
N-(Methoxycarbonyl) Maleimide structure
N-(Methoxycarbonyl) Maleimide structure
Product Name:N-(Methoxycarbonyl) Maleimide
CAS No:55750-48-6
MF:C6H5NO4
MW:155.108201742172
MDL:MFCD00042755
CID:384095
PubChem ID:580610
Update Time:2025-05-23

N-(Methoxycarbonyl) Maleimide Chemical and Physical Properties

Names and Identifiers

    • Methyl 2,5-dioxo-2,5-dihydro-1H-pyrrole-1-carboxylate
    • methyl 2,5-dihydro-2,5-dioxo-1H-pyrrole-1-carboxylate
    • 2,5-Dihydro-2,5-dioxo-1H-pyrrole-1-carboxylic acid methyl ester
    • 2,5-Dioxo-2,5-dihydro-1H-pyrrole-1-carboxylic acid methyl ester
    • 2,5-Dioxo-3-pyrroline-1-carboxylic acid methyl ester
    • Einecs 259-792-3
    • N-(CarboMethoxy)MaleiMide
    • 1H-Pyrrole-1-carboxylic acid, 2,5-dihydro-2,5-dioxo-, Methyl ester
    • N-Methoxycarbonylmaleimide
    • N-(Methoxycarbonyl) Maleimide
    • methyl 2,5-dioxo-2H-pyrrole-1(5H)-carboxylate
    • methyl 2,5-dioxopyrrole-1-carboxylate
    • N-(Methoxycarbonyl)
    • N-(Methoxycarbonyl)maleimide
    • LLAZQXZGAVBLRX-UHFFFAOYSA-N
    • AK116103
    • n-carbomethoxymaleimide
    • n-methoxycarbonyl-maleimide
    • n-methoxycarbonylmaleinimide
    • n-methoxycarbonyl maleinimide
    • methyl 2
    • GS-6678
    • N-(Methoxycarbonyl)-maleimide
    • EN300-214546
    • MFCD00042755
    • AMY362
    • Methyl 2,5-dioxo-2,5-dihydro-1H-pyrrole-1-carboxylate #
    • SCHEMBL320438
    • SY052182
    • FT-0671185
    • M2333
    • H10300
    • 55750-48-6
    • CS-W008141
    • N-Methoxycarbonylmaleimide, >=97.0% (N)
    • A870104
    • NS00033385
    • Z1255486023
    • BP-21525
    • AKOS016010340
    • DTXSID70204311
    • MDL: MFCD00042755
    • Inchi: 1S/C6H5NO4/c1-11-6(10)7-4(8)2-3-5(7)9/h2-3H,1H3
    • InChI Key: LLAZQXZGAVBLRX-UHFFFAOYSA-N
    • SMILES: O(C)C(N1C(C=CC1=O)=O)=O

Computed Properties

  • Exact Mass: 155.02200
  • Monoisotopic Mass: 155.021858
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 1
  • Complexity: 237
  • 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: -0.3
  • Topological Polar Surface Area: 63.7

Experimental Properties

  • Color/Form: Reddish crystal
  • Density: 1.496±0.06 g/cm3 (20 oC 760 Torr),
  • Melting Point: 64.0 to 68.0 deg-C
  • Boiling Point: 242.5°C at 760 mmHg
  • Flash Point: 100.4±22.6 oC,
  • Refractive Index: 1.545
  • Solubility: Dissolution (81 g/l) (25 o C),
  • PSA: 63.68000
  • LogP: -0.38430
  • Solubility: Not available
  • Sensitiveness: Heat sensitive

N-(Methoxycarbonyl) Maleimide Security Information

  • Signal Word:Warning
  • Hazard Statement: H302-H317
  • Warning Statement: P280
  • Hazardous Material transportation number:NONH for all modes of transport
  • WGK Germany:3
  • Safety Instruction: S22; S24/25
  • FLUKA BRAND F CODES:10
  • Storage Condition:0-10°C

N-(Methoxycarbonyl) Maleimide 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%

N-(Methoxycarbonyl) Maleimide Pricemore >>

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Additional information on N-(Methoxycarbonyl) Maleimide

N-(Methoxycarbonyl) Maleimide: A Versatile Reagent in Chemical and Biological Research

N-(Methoxycarbonyl) Maleimide (CAS No. 55750-48-6) is a highly versatile reagent that has gained significant attention in the fields of chemical and biological research. This compound, also known as Methyl N-Maleimidoformate, is a key intermediate in the synthesis of various bioconjugates, pharmaceuticals, and materials. Its unique chemical structure and reactivity make it an essential tool for researchers working on protein modification, drug delivery systems, and polymer chemistry.

The maleimide functional group in N-(Methoxycarbonyl) Maleimide is particularly reactive towards thiol groups (-SH), which are commonly found in cysteine residues of proteins. This reactivity allows for the formation of stable thioether bonds, making it an ideal choice for site-specific protein labeling and conjugation. The methoxycarbonyl group, on the other hand, provides additional functionalization options, enabling further modifications and conjugations.

Recent advancements in the field have highlighted the importance of N-(Methoxycarbonyl) Maleimide in the development of targeted drug delivery systems. For instance, a study published in the Journal of Medicinal Chemistry demonstrated the use of this compound to create site-specific antibody-drug conjugates (ADCs). The researchers utilized the maleimide group to conjugate a cytotoxic payload to a specific cysteine residue on an antibody, resulting in improved therapeutic efficacy and reduced off-target effects.

In addition to its applications in drug delivery, N-(Methoxycarbonyl) Maleimide has also been extensively studied for its role in polymer chemistry. The maleimide group can participate in various polymerization reactions, such as thiol-maleimide click chemistry, which is widely used to create well-defined polymers with precise control over molecular weight and architecture. This has led to the development of novel materials with tunable properties for applications ranging from tissue engineering to electronic devices.

The synthetic accessibility of N-(Methoxycarbonyl) Maleimide further enhances its utility. It can be readily prepared from commercially available maleic anhydride through a series of straightforward reactions. The ease of synthesis and high purity of the final product make it a cost-effective choice for large-scale applications.

From a safety perspective, N-(Methoxycarbonyl) Maleimide is generally considered safe for laboratory use when proper handling and storage protocols are followed. However, it is important to note that like many chemical reagents, it should be handled with care to avoid skin contact and inhalation. Proper personal protective equipment (PPE) such as gloves and goggles should be worn during handling.

In conclusion, N-(Methoxycarbonyl) Maleimide (CAS No. 55750-48-6) is a powerful reagent with a wide range of applications in chemical and biological research. Its unique chemical properties make it an indispensable tool for researchers working on protein modification, drug delivery systems, and polymer chemistry. As ongoing research continues to uncover new possibilities, this compound is likely to remain at the forefront of scientific innovation.

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