18196-80-0

Basic information

• Product Name: N-(3-CHLOROPHENYL)MALEAMIC ACID
• Synonyms: (2Z)-4-[(3-CHLOROPHENYL)AMINO]-4-OXOBUT-2-ENOIC ACID;ASISCHEM Z42962;N-(M-CHLOROPHENYL)MALEAMIC ACID;OTAVA-BB BB7010590151;N-(3-CHLOROPHENYL)MALEAMIC ACID;Maleic acid mono(3-chlorophenyl)amide;(2E)-4-[(3-Chlorophenyl)amino]-4-oxobut-2-enoic acid;(Z)-4-[(3-chlorophenyl)amino]-4-keto-but-2-enoic acid
• CAS NO: 18196-80-0
• Molecular Formula: C₁₀H₈ClNO₃
• Molecular Weight: 225.63
• EINECS: -0
• Mol File: 18196-80-0.mol

Chemical Properties

• Melting Point: 197-198°C
• Boiling Point: 463.9 °C at 760 mmHg
• Flash Point: 234.3 °C
• Appearance: /
• Density: 1.448 g/cm³
• Vapor Pressure: 2.1E-09mmHg at 25°C
• BRN: 2727601
• CAS DataBase Reference: N-(3-CHLOROPHENYL)MALEAMIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: N-(3-CHLOROPHENYL)MALEAMIC ACID(18196-80-0)
• EPA Substance Registry System: N-(3-CHLOROPHENYL)MALEAMIC ACID(18196-80-0)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36
• Hazardous Substances Data: 18196-80-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
N-(3-CHLOROPHENYL)MALEAMIC ACID is used as a building block for the synthesis of pharmaceuticals and agrochemicals, leveraging its unique chemical structure to create novel compounds with therapeutic or pesticidal properties.
Used in Organic Synthesis:
N-(3-CHLOROPHENYL)MALEAMIC ACID is utilized as a chemical intermediate in organic synthesis, contributing to the formation of complex organic molecules for various applications.
Used in Research and Development:
N-(3-CHLOROPHENYL)MALEAMIC ACID is studied for its potential biological activities and therapeutic properties, exploring its capacity to contribute to the development of new drugs and treatments.

InChI:InChI=1/C10H8ClNO3/c11-7-2-1-3-8(6-7)12-9(13)4-5-10(14)15/h1-6H,(H,12,13)(H,14,15)/p-1/b5-4+

Upstream product

• 108-31-6 maleic anhydride 
• 108-42-9 3-chloro-aniline 

Downstream Products

• 54012-45-2 N-(3-chloro-phenyl)-2-[3-(4-methyl-anilino)-4-oxo-2-thioxo-thiazolidin-5-yl]-acetamide 
• 95516-21-5 (Z)-3-(3-Chloro-phenylcarbamoyl)-acrylic acid methyl ester 
• 96824-23-6 (Z)-3-(3-Chloro-phenylcarbamoyl)-acrylic acid ethyl ester 
• 107125-44-0 (Z)-4-[(E)-3-Chloro-phenylimino]-4-ethoxy-but-2-enoic acid 
• 1313395-67-3 N⁽¹⁾-(3-chlorophenyl)-N⁽⁴⁾-phenylmaleamide 
• 1313395-78-6 N⁽¹⁾-(3-chlorophenyl)-N⁽⁴⁾-phenylfumaramide 
• 1204-35-9 N-(3-chlorophenyl)maleimide 
• 106691-40-1 N-(3-chlorophenyl)-2-(3-oxo-1,4-benzothiazin-2-yl) acetamide 
• 915711-60-3 (E)-3-(3-Chloro-phenylcarbamoyl)-acrylic acid methyl ester 
• 96824-24-7 (Z)-3-(3-Chloro-phenylcarbamoyl)-acrylic acid propyl ester 
• 54012-38-3 2-(3-anilino-4-oxo-2-thioxo-thiazolidin-5-yl)-N-(3-chloro-phenyl)-acetamide 

Relevant articles and documents

A rapid and simple amine-catalyzed microwave-assisted isomerization of maleamides into fumaramides

An improved, efficient, and simple method for the synthesis of nonsymmetrical diamides of fumaric acid is reported. Starting from commercially available substrates, maleic diamides are formed in two steps, and then isomerized in a focused microwave reactor in acetonitrile as the solvent in the presence of a catalytic amount of piperidine, giving the corresponding fumaramides in high yields and purity.

Synthesis and in vitro evaluation of N-substituted maleimide derivatives as selective monoglyceride lipase inhibitors

The endocannabinoid 2-arachidonoylglycerol (2-AG) plays a major role in many physiological processes, and its action is quickly terminated via enzymatic hydrolysis catalyzed by monoglyceride lipase (MGL). Regulating its endogenous level could offer therapeutic opportunities; however, few selective MGL inhibitors have been described so far. Here, we describe the synthesis of N-substituted maleimides and their pharmacological evaluation on the recombinant human fatty acid amide hydrolase (FAAH) and on the purified human MGL. A few N-arylmaleimides were previously described (Saario, S. M.; Salo, O. M.; Nevalainen, T.; Poso, A.; Laitinen, J. T.; Jarvinen, T.; Niemi, R. Characterization of the Sulfhydryl-Sensitive Site in the Enzyme Responsible for Hydrolysis of 2-Arachidonoylglycerol in Rat Cerebellar Membranes. Chem. Biol. 2005, 12, 649-656) as MGL inhibitors, and along these lines, we present a new set of maleimide derivatives that showed low micromolar IC50 and high selectivity toward MGL vs FAAH. Then, structure-activity relationships have been investigated and, for instance, 1-biphenyl-4-ylmethylmaleimide inhibits MGL with an IC50 value of 790 nM. Furthermore, rapid dilution experiments reveal that these compounds act as irreversible inhibitors. In conclusion, N-substituted maleimides constitute a promising class of potent and selective MGL inhibitors.

Substituent chemical shifts of N-arylsuccinanilic acids, N-arylsuccinimides, N-arylmaleanilic acids, and N-arylmaleimides

NMR spectra of a series of N-arylsuccinanilic acids, N-arylsuccinimides, N-arylmaleanilic acids, and N-arylmaleimides were examined to estimate the electronic effect of the amide and imide groups on the chemical shifts of the hydrogen and carbon nuclei of the benzene ring.

Synthesis and antifungal activity of N-(alkyl/aryl)-2-(3-oxo-1,4- benzothiazin-2-yl)acetamide

A series of N-(alkyl/aryl)-2-(3-oxo-1,4-benzothiazin-2-yl)acetamide have been synthesized by condensation of substituted amines with maleic anhydride (MA) followed by cyclization with o-aminothiophenol (o-ATP). All the compounds have been screened for their antifungal activity against Tricophyton rubrum, Epidermophyton floccosum and Malassazia furfur. In the primary screening, some of the compounds exhibited appreciable activity. The structures of the synthesized compounds 7a-z have been established on the basis of elemental analysis and spectral data.

INFLUENCE OF MEDIUM AND SUBSTITUENTS ON ACYLATION OF AROMATIC AMINES AND THEIR POLYMERIC ANALOGS WITH MALEIC ANHYDRIDE

Correlation relationships describing the influence of substituents and solvents on the rate of acylation of aromatic amines and their polymeric analogs with maleic anhydride have been derived.

Esterification of Maleanilic Acids: Intramolecular Esterification Through Imidate Ester

Maleanilic acids are easily esterified at room temperature with an abs. alcohol in the presence of thionyl chloride.It has been shown to proceed through an intramolecular migration of alkyl group of the intermediate imidate ester.