26367-48-6

Basic information

• Product Name: 3-Chlorocarbonylacrylic acid ethyl ester
• Synonyms: 3-Chlorocarbonylacrylic acid ethyl ester;ethyl fumaryl;(e)-4-chloro-4-oxo-2-butenoic acid ethyl ester;3-Chlorocarbonylacrilicacid ethylester;Ethyl fuMaroyl chloride;ethyl 4-chloro-4-oxobut-2-enoate;Ethyl fumaryl chloride;Ethyl fumaroyl chloride >=97.0%
• CAS NO: 26367-48-6
• Molecular Formula: C₆H₇ClO₃
• Molecular Weight: 162.57
• EINECS: 200-258-5
• Mol File: 26367-48-6.mol
• Article Data: 45

Chemical Properties

• Melting Point: 16 °C
• Boiling Point: 218°C
• Flash Point: 93°C
• Appearance: /
• Density: 1.220
• Vapor Pressure: 0.131mmHg at 25°C
• Refractive Index: n20/D1.463
• CAS DataBase Reference: 3-Chlorocarbonylacrylic acid ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Chlorocarbonylacrylic acid ethyl ester(26367-48-6)
• EPA Substance Registry System: 3-Chlorocarbonylacrylic acid ethyl ester(26367-48-6)

Safety Data

• Hazard Codes: C
• Statements: 22-34-43
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3265 8 / PGII
• WGK Germany: 3
• Hazardous Substances Data: 26367-48-6(Hazardous Substances Data)

Usage

General Description

3-Chlorocarbonylacrylic acid ethyl ester is a chemical compound that belongs to the category of chloroacrylic acids and derivatives. Its systematic name is Ethyl 3-chloro-2-oxopropanoate. This chemical is generally used as an intermediate in organic synthesis, specifically in the production of various pharmaceuticals and agrochemicals. It can also serve as a useful reagent in the field of medicinal and synthetic organic chemistry. It is important to handle this chemical with care, as reactive organohalides can form in certain conditions and be potentially dangerous to the handler.

InChI:InChI=1/C6H7ClO3/c1-2-10-6(9)4-3-5(7)8/h3-4H,2H2,1H3/b4-3+

Upstream product

• 64-17-5 ethanol 
• 627-63-4 fumaryl dichloride 
• 2459-05-4 malonic acid monoethyl ester 
• 623-91-6 diethyl Fumarate 
• 79-37-8 oxalyl dichloride 
• 2459-05-4 (E)-4-ethoxy-4-oxobut-2-enoic acid 
• 108-31-6 maleic anhydride 

Downstream Products

• 148533-21-5 (E)-But-2-enedioic acid ethyl ester 2-[2-(2-hydroxy-ethoxy)-ethoxy]-ethyl ester 
• 307499-97-4 ethyl-(E)-3-[N-(phenylmethoxy)carbamoyl]-2-propenoate 
• 152906-43-9 (E)-3-({4-Chloro-2-[(2-chloro-phenyl)-hydroxy-methyl]-phenyl}-methyl-carbamoyl)-acrylic acid ethyl ester 
• 152906-93-9 (E)-3-({4-Chloro-2-[(2-chloro-phenyl)-hydroxy-methyl]-phenyl}-ethyl-carbamoyl)-acrylic acid ethyl ester 
• 406684-68-2 (E)-3-({4-Chloro-2-[(2-chloro-phenyl)-hydroxy-methyl]-phenyl}-isopropyl-carbamoyl)-acrylic acid ethyl ester 
• 406684-70-6 (E)-3-[[4-Chloro-2-(hydroxy-phenyl-methyl)-phenyl]-(2,2-dimethyl-propyl)-carbamoyl]-acrylic acid ethyl ester 
• 152907-06-7 (E)-3-({4-Chloro-2-[(2-chloro-phenyl)-hydroxy-methyl]-phenyl}-propyl-carbamoyl)-acrylic acid ethyl ester 
• 152906-95-1 ethyl 3-[N-[4-chloro-2-(2-chloro-α-hydroxybenzyl)phenyl]-N-isobutylcarbamoyl]acrylate 
• 152910-49-1 (E)-3-({4-Chloro-2-[(2-chloro-phenyl)-hydroxy-methyl]-phenyl}-cyclopropylmethyl-carbamoyl)-acrylic acid ethyl ester 
• 204502-82-9 (E)-3-(Butyl-{4-chloro-2-[(2-chloro-phenyl)-hydroxy-methyl]-phenyl}-carbamoyl)-acrylic acid ethyl ester 
• 152907-00-1 (E)-3-[{4-Chloro-2-[(2-chloro-phenyl)-hydroxy-methyl]-phenyl}-(3-methyl-butyl)-carbamoyl]-acrylic acid ethyl ester 
• 152911-94-9 (E)-3-[{4-Chloro-2-[hydroxy-(2-methoxy-phenyl)-methyl]-phenyl}-(2,2-dimethyl-propyl)-carbamoyl]-acrylic acid ethyl ester 
• 152907-03-4 (E)-3-[{4-Chloro-2-[(2-chloro-phenyl)-hydroxy-methyl]-phenyl}-(1-ethyl-propyl)-carbamoyl]-acrylic acid ethyl ester 
• 406684-69-3 (E)-3-[{3-Chloro-2-[(2-chloro-phenyl)-hydroxy-methyl]-phenyl}-(2,2-dimethyl-propyl)-carbamoyl]-acrylic acid ethyl ester 

Relevant articles and documents

[3+2] Cycloaddition of o-nitrophenyl azide to 3a,6-epoxyisoindoles

[3+2] Cycloaddition of o-nitrophenyl azide to the multiple bond of oxabicyclo[2.2.1]heptene moiety in substituted 3a,6-epoxyisoindoles was performed. The 1,3-dipolar addition reaction proceeded stereoselectively, producing a pair of isomeric cis-4,8a-epox

Primaquine and chloroquine fumardiamides as promising antiplasmodial agents

This paper describes a continuation of our efforts in the pursuit of novel antiplasmodial agents with optimized properties. Following our previous discovery of biologically potent asymmetric primaquine (PQ) and halogenaniline fumardiamides (1–6), we now report their significant in vitro activity against the hepatic stages of Plasmodium parasites. Furthermore, we successfully prepared chloroquine (CQ) analogue derivatives (11–16) and evaluated their activity against both the hepatic and erythrocytic stages of Plasmodium. Our results have shown that PQ fumardiamides (1–6) exert both higher activity against P. berghei hepatic stages and lower toxicity against human hepatoma cells than the parent drug and CQ derivatives (11–16). The favourable cytotoxicity profile of the most active compounds, 5 and 6, was corroborated by assays performed on human cells (human breast adenocarcinoma (MCF-7) and non-tumour embryonic kidney cells (HEK293T)), even when glucose-6-phosphate dehydrogenase (G6PD) was inhibited. The activity of CQ fumardiamides on P. falciparum erythrocytic stages was higher than that of PQ derivatives, comparable to CQ against CQ-resistant strain PfDd2, but lower than CQ when tested on the CQ-sensitive strain Pf3D7. In addition, both sets of compounds showed favourable drug-like properties. Hence, quinoline fumardiamides could serve as a starting point towards the development of safer and more effective antiplasmodial agents.

SAHAquines, Novel Hybrids Based on SAHA and Primaquine Motifs, as Potential Cytostatic and Antiplasmodial Agents

We report the synthesis of SAHAquines and related primaquine (PQ) derivatives. SAHAquines are novel hybrid compounds that combine moieties of suberoylanilide hydroxamic acid (SAHA), an anticancer agent with weak antiplasmodial activity, and PQ, an antimalarial drug with low antiproliferative activity. The preparation of SAHAquines is simple, cheap, and high yielding. It includes the following steps: coupling reaction between primaquine and a dicarboxylic acid monoester, hydrolysis, a new coupling reaction with O-protected hydroxylamine, and deprotection. SAHAquines 5 a–d showed significant reduction in cell viability. Among the three human cancer cell lines (U2OS, HepG2, and MCF-7), the most responsive were the MCF-7 cells. The antibodies against acetylated histone H3K9/H3K14 in MCF-7 cells revealed a significant enhancement following treatment with N-hydroxy-N′-{4-[(6-methoxyquinolin-8-yl)amino]pentyl}pentanediamide (5 b). Ethyl (2E)-3-({4-[(6-methoxyquinolin-8-yl)amino]pentyl}carbamoyl)prop-2-enoate (2 b) and SAHAquines were the most active compounds against both the hepatic and erythrocytic stages of Plasmodium parasites, some of them at sub-micromolar concentrations. The results of our research suggest that SAHAquines are promising leads for new anticancer and antimalarial agents.

Enantioselective Synthesis of N-Alkylamines through β-Amino C-H Functionalization Promoted by Cooperative Actions of B(C6F5)3and a Chiral Lewis Acid Co-Catalyst

We disclose a catalytic method for β-C(sp3)-H functionalization of N-alkylamines for the synthesis of enantiomerically enriched β-substituted amines, entities prevalent in pharmaceutical compounds and used to generate different families of chiral catalysts. We demonstrate that a catalyst system comprising of seemingly competitive Lewis acids, B(C6F5)3, and a chiral Mg- or Sc-based complex, promotes the highly enantioselective union of N-alkylamines and α,β-unsaturated compounds. An array of δ-amino carbonyl compounds was synthesized under redox-neutral conditions by enantioselective reaction of a N-alkylamine-derived enamine and an electrophile activated by the chiral Lewis acid co-catalyst. The utility of the approach is highlighted by late-stage β-C-H functionalization of bioactive amines. Investigations in regard to the mechanistic nuances of the catalytic processes are described.