1-(3-chloro-4-methylphenyl)-1H-pyrrole-2,5-dione

Base Information

• Chemical Name: 1-(3-chloro-4-methylphenyl)-1H-pyrrole-2,5-dione
• CAS No.: 52845-68-8
• Molecular Formula: C11H8ClNO2
• Molecular Weight: 221.643
• European Community (EC) Number: 651-949-8
• DSSTox Substance ID: DTXSID10351696
• Nikkaji Number: J1.844.002D
• Wikidata: Q82128302
• ChEMBL ID: CHEMBL4537139
• Mol file: 52845-68-8.mol

Synonyms:52845-68-8;1-(3-chloro-4-methylphenyl)-1H-pyrrole-2,5-dione;N-(4-METHYL-3-CHLOROPHENYL)MALEIMIDE;1-(3-chloro-4-methylphenyl)pyrrole-2,5-dione;1-(3-chloro-4-methylphenyl)-2,5-dihydro-1H-pyrrole-2,5-dione;N-(3-Chloro-4-methylphenyl)maleimide;F0913-1858;SCHEMBL8005849;CHEMBL4537139;DTXSID10351696;MFCD00086930;STK040224;AKOS000296055;AS-67974;CS-0307644;EU-0074459;FT-0605610;EN300-03979;D95961;1-(3-Chloro-4-methylphenyl)pyrroline-2,5-dione;A917897;Z56899086

Chemical Property of 1-(3-chloro-4-methylphenyl)-1H-pyrrole-2,5-dione

Chemical Property:

• Vapor Pressure: 6.81E-06mmHg at 25°C
• Melting Point: 144-148 °C
• Refractive Index: 1.625
• Boiling Point: 377.3 °C at 760 mmHg
• PKA: -1.44±0.20(Predicted)
• Flash Point: 182 °C
• PSA: 37.38000
• Density: 1.398 g/cm³
• LogP: 2.14280
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 221.0243562
• Heavy Atom Count: 15
• Complexity: 309

Purity/Quality:

99% ^*data from raw suppliers

1-(3-Chloro-4-methylphenyl)-1H-pyrrole-2,5-dione ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C=C(C=C1)N2C(=O)C=CC2=O)Cl

Technology Process of 1-(3-chloro-4-methylphenyl)-1H-pyrrole-2,5-dione

There total 3 articles about 1-(3-chloro-4-methylphenyl)-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:

C11H10ClNO3 → N-(3-chloro,4-methylphenyl)maleimide (52845-68-8)

Guidance literature:

With sodium acetate; In acetic anhydride; for 1.5h; Reflux;

DOI:10.1021/acs.joc.8b01520

Reference yield:

3-chloro-p-toluidine (95-74-9,827571-80-2) → N-(3-chloro,4-methylphenyl)maleimide (52845-68-8)

Guidance literature:

Multi-step reaction with 2 steps

1: diethyl ether / 1.5 h / 25 °C

2: sodium acetate / acetic anhydride / 1.5 h / Reflux

With sodium acetate; In diethyl ether; acetic anhydride;

DOI:10.1021/acs.joc.8b01520

Reference yield:

maleic anhydride (108-31-6) + 3-chloro-p-toluidine (95-74-9,827571-80-2) → N-(3-chloro,4-methylphenyl)maleimide (52845-68-8)

Guidance literature:

maleic anhydride; 3-chloro-p-toluidine; In N,N-dimethyl-formamide; at 20 ℃; for 2.5h;

With sodium acetate trihydrate; acetic anhydride; triethylamine; hydroquinone; In N,N-dimethyl-formamide; at 75 ℃;

DOI:10.1002/adsc.201900843

upstream raw materials:

3-chloro-p-toluidine

maleic anhydride

Downstream raw materials:

1-(3-chloro-4-methylphenyl)-3-{2-[(1-ethylpropylidene)hydrazono]-1-methylbutyl}pyrrolidine-2,5-dione

1-(3-chloro-4-methylphenyl)-3-[2-(cyclopentylidenehydrazono)cyclopentyl]pyrrolidine-2,5-dione

N-(3-chloro-4-methylphenyl)-2-(3,4,4a,5,6,7-hexahydro-3-oxo-2H-cyclopenta[c]pyridazin-4-yl)acetamide

1-(3-chloro-4-methylphenyl)-3-[2-(cyclohexylidenehydrazono)cyclohexyl]pyrrolidine-2,5-dione

Refernces

• 1、 Zhang, Hua,Zhan, Xiao-Yu,Chen, Xu-Ling,Tang, Lei,He, Shuai,Shi, Zhi-Chuan,Wang, Yu,Wang, Ji-Yu. "Iron(III) Chloride/Phenylsilane-Mediated Cascade Reaction of Allyl Alcohols with Maleimides: Synthesis of Poly-Substituted γ-Butyrolactones". supporting information. p. 4919 - 4925. Retrieved 2019/11/03.