80818-24-2

Basic information

• Product Name: (Z)-(2-methyl-4-(4-nitrophenylamino)-4-oxo)but-2-enoic acid
• Synonyms: (Z)-(2-methyl-4-(4-nitrophenylamino)-4-oxo)but-2-enoic acid
• CAS NO: 80818-24-2
• Molecular Weight: 250.211
• Mol File: 80818-24-2.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (Z)-(2-methyl-4-(4-nitrophenylamino)-4-oxo)but-2-enoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-(2-methyl-4-(4-nitrophenylamino)-4-oxo)but-2-enoic acid(80818-24-2)
• EPA Substance Registry System: (Z)-(2-methyl-4-(4-nitrophenylamino)-4-oxo)but-2-enoic acid(80818-24-2)

Safety Data

• Hazardous Substances Data: 80818-24-2(Hazardous Substances Data)

Upstream product

• 616-02-4 citraconic acid anhydride 
• 100-01-6 4-nitro-aniline 

Downstream Products

• 80818-21-9 (Z)-2-methyl-4-oxo-4-(phenylamino)but-2-enoic acid 
• 107855-34-5 2-((Z)-3-Carboxy-2-methyl-acryloylamino)-benzoic acid 
• 107855-35-6 2-((Z)-3-Carboxy-but-2-enoylamino)-benzoic acid 
• 616-02-4 citraconic acid anhydride 
• 80818-11-7 (Z)-(3-methyl-4-(4-nitrophenylamino)-4-oxo)but-2-enoic acid 
• 100-01-6 4-nitro-aniline 
• 80818-08-2 3-methyl-3-phenylcarbamoyl-acrylic acid 
• 4338-06-1 N-(4-nitrophenyl)maleimide 
• 37904-11-3 3-chloro-1-(4-nitrophenyl)pyrrolidine-2,5-dione 
• 134939-24-5 1-(4-bromophenyl)-3-methyl-1H-pyrrole-2,5-dione 
• 59648-09-8 1-(4-chlorophenyl)-3-methyl-1H-pyrrole-2,5-dione 
• 10490-21-8 3-methyl-1-(4-nitrophenyl)-1H-pyrrole-2,5-dione 
• 76738-06-2 1-(4-methoxyphenyl)-3-methyl-1H-pyrrole-2,5-dione 
• 3120-12-5 3-methyl-1-(p-tolyl)-1H-pyrrole-2,5-dione 

Relevant articles and documents

Substituent effects on the regioselectivity of maleamic acid formation and hydrogen chloride addition to N-aryl maleimides

Itaconic anhydride reacts with aryl amines to give a substituent controlled equilibrium mixture of regioisomeric (Z)-2-methyl- and (Z)-3-methyl-4-oxo-4- (arylamino)but-2-enoic acids. Electron-donating groups favor nucleophilic attack on C-5 carbonyl, while the presence of electron-withdrawing groups enhances the bias for attack on C-2 carbonyl. The treatment of (Z)-2-methyl- and (Z)-3-methyl-4-oxo-4-(arylamino)but-2-enoic acids with SOCl2-Et 3N in THF provided the corresponding maleimides in high yields while under the same conditions the maleic anhydride aryl amine addition products gave predominately the corresponding 3-chloro-1-arylpyrrolidine-2,5-diones and maleimides in substituent dependent ratio. TUeBITAK, 2012.