1-(4-Acetylphenyl)-1H-pyrrole-2,5-dione

Base Information

• Chemical Name: 1-(4-Acetylphenyl)-1H-pyrrole-2,5-dione
• CAS No.: 1082-85-5
• Molecular Formula: C12H9NO3
• Molecular Weight: 215.208
• Hs Code.: 2925190090
• European Community (EC) Number: 214-106-1
• NSC Number: 209075
• UNII: PPX4Y26HKM
• DSSTox Substance ID: DTXSID10148462
• Nikkaji Number: J217.207K
• Wikidata: Q69757165
• Mol file: 1082-85-5.mol

Synonyms:1-(4-Acetylphenyl)-1H-pyrrole-2,5-dione;1082-85-5;n-(4-acetylphenyl)maleimide;1-(4-acetylphenyl)pyrrole-2,5-dione;PPX4Y26HKM;EINECS 214-106-1;NSC-209075;1-(4-acetylphenyl)-2,5-dihydro-1H-pyrrole-2,5-dione;N-(4-Acetylphenyl)Maleinimide;MFCD00014537;NSC209075;Cyto8G9;p-maleimidoacetophenone;UNII-PPX4Y26HKM;CBMicro_026329;N-(p-Acetylphenyl)maleimide;SCHEMBL371252;DTXSID10148462;BBL018919;STL015405;AKOS000296063;NSC 209075;1-(4-acetylphenyl)-pyrrole-2,5-dione;BIM-0026282.P001;FT-0629194;EN300-17192;D95959;AB00673634-01;6T-0056;A801836;J-503222;Z56899062

Chemical Property of 1-(4-Acetylphenyl)-1H-pyrrole-2,5-dione

Chemical Property:

• Vapor Pressure: 1.01E-06mmHg at 25°C
• Melting Point: 153-156 °C
• Refractive Index: 1.613
• Boiling Point: 403.6 °C at 760 mmHg
• PKA: -3.77±0.20(Predicted)
• Flash Point: 195.6 °C
• PSA: 54.45000
• Density: 1.33 g/cm³
• LogP: 1.38360
• Water Solubility.: Insoluble in water.
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 215.058243149
• Heavy Atom Count: 16
• Complexity: 347

Purity/Quality:

98%,99%, ^*data from raw suppliers

1-(4-Acetylphenyl)-1H-pyrrole-2,5-dione ^*data from reagent suppliers

Safty Information:

• Pictogram(s): XnXi
• Hazard Codes: Xn,Xi
• Statements: 36/37/38-22
• Safety Statements: 37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1=CC=C(C=C1)N2C(=O)C=CC2=O
• Uses: N-(4-Acetylphenyl)maleimide is used as cross linking agent for reversible conjugation of thiol- containing compounds.

Technology Process of 1-(4-Acetylphenyl)-1H-pyrrole-2,5-dione

There total 6 articles about 1-(4-Acetylphenyl)-1H-pyrrole-2,5-dione which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 75.59%

maleic anhydride (108-31-6) + p-aminobenzophenone (99-92-3) → 1-(4-acetylphenyl)-1H-pyrrole-2,5-dione (1082-85-5)

Guidance literature:

With acetic acid; for 2h; Reflux;

DOI:10.1016/j.bmcl.2020.127655

Reference yield: 52.6%

N-phenyl-maleimide (941-69-5) + acetyl chloride (75-36-5) → 1-(4-acetylphenyl)-1H-pyrrole-2,5-dione (1082-85-5)

Guidance literature:

With aluminium trichloride; In nitrobenzene; at 0 ℃; for 3h;

DOI:10.1007/BF00954385

Reference yield:

(Z)-4-(4-acetylphenylamino)-4-oxobut-2-enoic acid (24870-12-0) → 1-(4-acetylphenyl)-1H-pyrrole-2,5-dione (1082-85-5)

Guidance literature:

With sodium acetate; acetic anhydride; at 75 ℃;

DOI:10.1016/j.bmcl.2010.01.098

upstream raw materials:

N-(4-acetyl-phenyl)-maleamic acid

N-phenyl-maleimide

acetyl chloride

maleic anhydride

Downstream raw materials:

1-(4-acetylphenyl)-3-(2,4-dioxopentan-3-yl)pyrrolidine-2,5-dione

1-(4-acetylphenyl)-3-(2,4,6-trinitrophenoxy)pyrrolidine-2,5-dione

1-(4-acetylphenyl)-3-(4-aminophenyloxy)pyrrolidine-2,5-dione

Refernces

• 1、 Cordeiro, Rachel,Kachroo, Monica. "Synthesis and biological evaluation of anti-tubercular activity of Schiff bases of 2-Amino thiazoles". . . Retrieved 2020.
• 2、 Patel, Jigarkumar R.,Dhorajiya, Bhaveshkumar D.,Dholakiya, Bharatkumar Z.,Badria, Farid A.,Ibrahim, Ahmed S.. "In-vitro cytotoxicity, antioxidant, bleomycin-dependent DNA damage and immunomodulatory evaluation of 1-(4-acetylphenyl)-3-aryloxypyrrolidine-2,5-dione based derivatives". . p. 3907 - 3915. Retrieved 2014/08/05.