1082-85-5

Basic information

• Product Name: N-(4-ACETYLPHENYL)MALEIMIDE
• Synonyms: 1-(4-Acetylphenyl)-1H-pyrrole-2,5-dione98%;N-(4-ACETYLPHENYL)MALEIMIDE;ASISCHEM D48957;1-(4-ACETYLPHENYL)-1H-PYRROLE-2,5-DIONE;1-(4-ACETYL-PHENYL)-PYRROLE-2,5-DIONE;N-(4-Acetylpenl)-2,5-maleimide;N-(4-Acetylphenyl)maleinimide;4'-maleimidoacetophenone
• CAS NO: 1082-85-5
• Molecular Formula: C₁₂H₉NO₃
• Molecular Weight: 215.2
• EINECS: 214-106-1
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts
• Mol File: 1082-85-5.mol
• Article Data: 8

Chemical Properties

• Melting Point: 153-156 °C
• Boiling Point: 403.6 °C at 760 mmHg
• Flash Point: 195.6 °C
• Appearance: /
• Density: 1.33 g/cm³
• Vapor Pressure: 1.01E-06mmHg at 25°C
• Refractive Index: 1.613
• PKA: -3.77±0.20(Predicted)
• Water Solubility: Insoluble in water.
• BRN: 157371
• CAS DataBase Reference: N-(4-ACETYLPHENYL)MALEIMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-(4-ACETYLPHENYL)MALEIMIDE(1082-85-5)
• EPA Substance Registry System: N-(4-ACETYLPHENYL)MALEIMIDE(1082-85-5)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 36/37/38-22
• Safety Statements: 37/39-26
• HazardClass: IRRITANT
• Hazardous Substances Data: 1082-85-5(Hazardous Substances Data)

Usage

Description

N-(4-Acetylphenyl)maleimide is an organic compound with the molecular formula C11H9NO2. It is a derivative of maleimide, featuring an acetylphenyl group attached to the nitrogen atom. N-(4-ACETYLPHENYL)MALEIMIDE is known for its ability to form reversible conjugations with thiol-containing compounds, making it a versatile molecule in various applications.

Uses

Used in Chemical Synthesis:
N-(4-Acetylphenyl)maleimide is used as a cross-linking agent for the reversible conjugation of thiol-containing compounds. This application is particularly useful in the field of chemical synthesis, where it can help create stable and functional molecules with specific properties.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, N-(4-Acetylphenyl)maleimide is utilized as a key intermediate in the synthesis of various drugs and drug candidates. Its ability to form reversible conjugations with thiol-containing compounds allows for the development of novel therapeutic agents with improved pharmacological properties.
Used in Biochemical Research:
N-(4-Acetylphenyl)maleimide is also employed in biochemical research as a tool to study the interactions between proteins and other biomolecules. By forming reversible conjugations with thiol groups, it can help researchers understand the structure and function of proteins, as well as their role in various biological processes.
Used in Material Science:
In the field of material science, N-(4-Acetylphenyl)maleimide can be used to develop new materials with specific properties. Its ability to form reversible conjugations with thiol-containing compounds can be exploited to create materials with enhanced stability, reactivity, or other desired characteristics.

InChI:InChI=1/C12H9NO3/c1-8(14)9-2-4-10(5-3-9)13-11(15)6-7-12(13)16/h2-7H,1H3

Upstream product

• 24870-12-0 N-(4-acetyl-phenyl)-maleamic acid 
• 941-69-5 N-phenyl-maleimide 
• 75-36-5 acetyl chloride 
• 108-31-6 maleic anhydride 
• 99-92-3 p-aminobenzophenone 
• 24870-12-0 (Z)-4-(4-acetylphenylamino)-4-oxobut-2-enoic acid 

Downstream Products

• 28202-80-4 1-(4-acetyl-phenyl)-3-((E)-6-amino-benzo[1,3]dioxol-5-ylmethylene)-pyrrolidine-2,5-dione 

Relevant articles and documents

SELECTIVITY OF THE ACYLATION OF N-PHENYLMALEIMIDE

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An approach to "escape from flatland": Chemo-enzymatic synthesis and biological profiling of a library of bridged bicyclic compounds

A major reason for the low success rate in current drug development through chemical synthesis has been ascribed to the large fraction of quasi planar candidate molecules. Therefore, an "escape from flatland" strategy has been recommended for the generation of bioactive chemical entities. In a first attempt to test this recommendation, we synthesized a small collection of bridged bicyclic compounds possessing a rigid spherical core structure by combining a group of cyclic dienes with a collection of dienophiles. We started from planar biphenyl analogues and, by enzymatic dioxygenation, transformed them into hydroxylated diene structures. Using a small library of newly synthesized dienophiles, the dienes were converted into bridged bicycles via the Diels-Alder reaction. The resulting collection of 78 structures was first tested for bioactivity in a generic assay based on interference with the proliferation of mammalian cells. A more mechanism-targeted bioactivity profiling method, exploiting cellular impedance monitoring, was subsequently used to obtain suggestions for the mode of action exerted by those compounds that were the most active in the proliferation assay. Proteasome inhibition could be confirmed for 8 of a series of 9 respective candidates. Whilst 7 of these molecules showed relatively weak interference with proteasome activity, one candidate exerted a moderate but distinct inhibition. This result appears remarkable in view of the small size of the compound library, which was synthesized following a few basic considerations. It encourages the application of diverse synthetic approaches to further investigate the role of spherical shape for the success of compound libraries.

Facile Michael-type addition of aromatic alcohols to N-(4-acetylphenyl) maleic imide

A one-pot, economical, and efficient synthesis of 1-(4-acetylphenyl)-3- aryloxypyrrolidine-2,5-diones has been accomplished in single steps and in satisfactory yields from 1-(4-acetylphenyl)-pyrrole-2,5-diones and aromatic alcohols. All the compounds were characterized by physical, spectroscopic, and elemental analysis.