7242-16-2

Basic information

• Product Name: N-(4-CHLOROPHENYL)MALEAMIC ACID
• Synonyms: ASISCHEM Z49193;N-(P-CHLOROPHENYL)MALEAMIC ACID;(2E)-4-[(4-chlorophenyl)amino]-4-oxobut-2-enoic acid;(Z)-4-((4-chlorophenyl)amino)-4-oxobut-2-enoic acid
• CAS NO: 7242-16-2
• Molecular Formula: C₁₀H₈ClNO₃
• Molecular Weight: 225.63
• Mol File: 7242-16-2.mol
• Article Data: 27

Chemical Properties

• Boiling Point: 466.2°C at 760 mmHg
• Flash Point: 235.7°C
• Appearance: /
• Density: 1.448g/cm³
• Vapor Pressure: 1.72E-09mmHg at 25°C
• Refractive Index: 1.642
• PKA: 2.73±0.25(Predicted)
• CAS DataBase Reference: N-(4-CHLOROPHENYL)MALEAMIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: N-(4-CHLOROPHENYL)MALEAMIC ACID(7242-16-2)
• EPA Substance Registry System: N-(4-CHLOROPHENYL)MALEAMIC ACID(7242-16-2)

Safety Data

• Hazardous Substances Data: 7242-16-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H8ClNO3/c11-7-1-3-8(4-2-7)12-9(13)5-6-10(14)15/h1-6H,(H,12,13)(H,14,15)/b6-5-

Upstream product

• 108-31-6 maleic anhydride 
• 106-47-8 4-chloro-aniline 

Downstream Products

• 1631-29-4 N-(4-chlorophenyl)maleimide 
• 850148-32-2 3-chloro-1-(4-chlorophenyl)succinimide 
• 19990-27-3 5-(4-chlorophenylimino)-5H-furan-2-one 
• 72889-95-3 (Z)-3-(4-Chloro-phenylcarbamoyl)-acrylic acid methyl ester 
• 132858-26-5 (3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-2-yl)-acetic acid-(4-chloro-anilide) 
• 86396-54-5 (E)-3-(4-Chloro-phenylcarbamoyl)-acrylic acid methyl ester 
• 6943-00-6 1-(4-chlorophenyl)pyrrolidine-2,5-dione 
• 29236-09-7 N-(4-chlorophenyl)-3,4-dichloromaleimide 
• 339090-36-7 2-(4-Chlorophenyl)-5,6-dimethyl-3a,4,7,7a-tetrahydroisoindole-1,3-dione 
• 105450-99-5 Cr(COOCHCHCONHC₆H₄Cl)3 
• 105367-01-9 [Ni(O₂CCHCHC(O)NH(C₆H₄)Cl)2(H₂O)2] 

Relevant articles and documents

Synthesis and biological evaluation of novel benzylidene-succinimide derivatives as noncytotoxic antiangiogenic inhibitors with anticolorectal cancer activity in vivo

A novel series of benzylidene-succinimide derivatives were synthesized, characterized and evaluated for their cytotoxicities against HCT116, and SW480 cancer cells and NCM460 normal human cells. Their antiangiogenic capabilities were evaluated using a chick chorioallantoic membrane (CAM) assay. The compound, XCF-37b, was selected as the most potent antiangiogenic inhibitor with noncytotoxicity to evaluate the pharmacological effects on human umbilical vein endothelial cells (HUVECs) and cancer cells in vivo and in vitro. The results showed that XCF-37b inhibited HT29-cell colon tumor growth in vivo, without showing cytotoxicity against the five other cancer cell lines in vitro. Experiments confirmed that XCF-37b had obvious antiangiogenic activity by HUVEC migration and invasion and rat aortic ring angiogenesis ex vivo. Mechanism studies showed that XCF-37b inhibited the AKT/mTOR and VEGFR2 signaling pathways, as evidenced by decreased expressions of phosphor-AKT (p-AKT), p-mTOR, p-VEGFR2 (Tyr175), p-Src (Tyr416), p-FAK (Tyr925), and p-Erk1/2 (Thr202/Tyr204). Moreover, XCF-37b significantly decreased the protein expressions of matrix metalloproteinase-2 (MMP-2), MMP-9 and hypoxia-inducible factor-1α (HIF-1α). XCF-37b generally regulated angiogenic inhibition through several regulatory pathways, without significantly interfering with colorectal cancer cell growth.

Triethylamine-catalyzed synthesis of oxazepine from maleamic acids

2-Thioxo-1,3-oxazepine-4,7-dione compounds were obtained via triethylamine-catalyzed condensation of maleamic acids with thiophosgene under anhydrous conditions. This method features relatively a simple methodology, use of inexpensive reagents, convenient operating conditions and high yields.

One-pot regioselective synthesis of novel 1-N-methyl-spiro[2,3']oxindole-spiro[3,3"]-1"-N-arylpyrrolidine-2",5"-dione-4-arylpyrrolidines through multicomponent 1,3-dipolar cycloaddition reaction of azomethine ylide

An atom economic and facile synthesis of novel dispiro-oxindole-pyrrolidines has been achieved via a three-component tandem cycloaddition of azomethine ylide generated in situ from isatin and sarcosine by decarboxylative condensation with N-aryl-3-benzylidene-pyrrolidine-2,5-dione derivatives as dipolarophiles. The salient features of synthetic procedure are characterized by the mild reaction conditions, high yields, high regioselectivity and stereoselectivity, one-pot procedure, and operational simplicity. This regioselectivity was assumed to be under the influence of π-π stacking interactions between the aromatic rings of azomethine ylide and N-aryl-3-benzylidene-pyrrolidine-2,5-diones that further control the exo-endo selectivity of the reaction 1,3-dipolar cycloaddition. The regiochemistry and structures of the cycloadducts were determined with spectroscopic data.