24755-82-6

Basic information

• Product Name: ETHYL 4-CHLORO-2-PHENYL-5-PYRIMIDINECARBOXYLATE
• Synonyms: ETHYL 4-CHLORO-2-PHENYL-5-PYRIMIDINECARBOXYLATE;4-Chloro-2-phenyl-5-pyrimidinecarboxylic acid ethyl ester;4-Chloro-5-carbethoxy-2-phenylpyrimidine;4-Chloro-5-ethoxycarbonyl-2-phenylpyrimidine;5-Carbethoxy-4-chloro-2-phenylpyrimidine;NSC 44687
• CAS NO: 24755-82-6
• Molecular Formula: C₁₃H₁₁ClN₂O₂
• Molecular Weight: 262.69
• Mol File: 24755-82-6.mol
• Article Data: 7

Chemical Properties

• Melting Point: 130-131°C
• Boiling Point: 317.2°Cat760mmHg
• Flash Point: 145.6°C
• Appearance: /
• Density: 1.265
• Vapor Pressure: 0.00039mmHg at 25°C
• Refractive Index: 1.572
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: ETHYL 4-CHLORO-2-PHENYL-5-PYRIMIDINECARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 4-CHLORO-2-PHENYL-5-PYRIMIDINECARBOXYLATE(24755-82-6)
• EPA Substance Registry System: ETHYL 4-CHLORO-2-PHENYL-5-PYRIMIDINECARBOXYLATE(24755-82-6)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 24755-82-6(Hazardous Substances Data)

Usage

General Description

ETHYL 4-CHLORO-2-PHENYL-5-PYRIMIDINECARBOXYLATE is a chemical compound that is mainly used in the pharmaceutical industry as a building block for the synthesis of various pharmaceutical products. It is a pyrimidinecarboxylate derivative, which is a class of organic compounds that has potential biological activity. ETHYL 4-CHLORO-2-PHENYL-5-PYRIMIDINECARBOXYLATE is known for its wide range of applications in medicinal chemistry, particularly in the development of antiviral, antifungal, and anticancer drugs. Additionally, it has been studied for its potential as an insecticide and herbicide due to its structural properties. Furthermore, it is also utilized as an intermediate in the synthesis of other organic compounds. Overall, ETHYL 4-CHLORO-2-PHENYL-5-PYRIMIDINECARBOXYLATE is a versatile chemical with diverse applications in various industries, particularly in the field of pharmaceuticals.

InChI:InChI=1/C13H11ClN2O2/c1-2-18-13(17)10-8-15-12(16-11(10)14)9-6-4-3-5-7-9/h3-8H,2H2,1H3

Upstream product

• 1670-14-0 benzamidine monohydrochloride 
• 55613-22-4 ethyl 4-oxo-2-phenyl-3,4-dihydropyrimidine-5-carboxylic acid 
• 87-13-8 diethyl 2-ethoxymethylenemalonate 
• 618-39-3 benzamidin 
• 55613-22-4 4-hydroxy-2-phenyl-5-pyrimidinecarboxylic acid ethyl ester 

Downstream Products

• 78494-30-1 4-tert-Butylperoxy-2-phenyl-pyrimidine-5-carboxylic acid ethyl ester 
• 135370-76-2 5-ethoxycarbonyl-4-(1,1-dimethylpropylperoxy)-2-phenylpyrimidin 
• 135370-77-3 5-ethoxycarbonyl-4-(1,1-diethylpropylperoxy)-2-phenylpyrimidin 
• 135370-78-4 5-ethoxycarbonyl-4-(1,1-dimethylpropargylperoxy)-2-phenylpyrimidin 
• 135370-91-1 5-ethoxycarbonyl-4-(1,1-dimethyl-4-phenylbutylperoxy)-2-phenylpyrimidin 
• 135370-87-5 5-ethoxycarbonyl-4-<1,1-dimethyl-3-(4-methylphenyl)-propylperoxy>-2-phenylpyrimidin 
• 135370-86-4 5-ethoxycarbonyl-4-<1,1-dimethyl-3-(2-methylphenyl)-propylperoxy>-2-phenylpyrimidin 
• 135370-85-3 5-ethoxycarbonyl-4-(1,1-dimethyl-3-phenyl-propylperoxy)-2-phenylpyrimidin 
• 135370-92-2 5-ethoxycarbonyl-4-(1,1-dimethyl-5-phenylpentylperoxy)-2-phenylpyrimidin 
• 135370-79-5 4-(2-cyclohexyl-2-propylperoxy)-5-ethoxycarbonyl-2-phenylpyrimidin 
• 135370-80-8 4-(2-cyclohexyl-1,1-dimethylethylperoxy)-5-ethoxycarbonyl-2-phenylpyrimidin 
• 135370-81-9 4-(3-cyclohexyl-1,1-dimethylpropylperoxy)-5-ethoxycarbonyl-2-phenylpyrimidin 
• 135370-82-0 4-(4-cyclohexyl-1,1-dimethylbutylperoxy)-5-ethoxycarbonyl-2-phenylpyrimidin 
• 135370-93-3 5-ethoxycarbonyl-4-(1,1-dimethyl-6-phenylhexylperoxy)-2-phenylpyrimidin 

Relevant articles and documents

Design and synthesis of phenoxypyridyl acetamide or aryl-oxodihydropurine derivatives for the development of novel pet ligands targeting the translocator protein 18 kDa (TSPO)

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Characterization of amide bond conformers for a novel heterocyclic template of N-acylhydrazone derivatives

Herein we describe NMR experiments and structural modifications of 4-methyl-2-phenylpyrimidine-N-acylhydrazone compounds (aryl-NAH) in order to discover if duplication of some signals in their 1H- and 13C-NMR spectra was related to a mixture of imine double bond stereoisomers (E/Z) or CO-NH bond conformers (syn and anti-periplanar). NMR data from NOEdiff, 2D-NOESY and 1H-NMR spectra at different temperatures, and also the synthesis of isopropylidene hydrazone revealed the nature of duplicated signals of a 4-methyl-2-phenylpyrimidine-N-acylhydrazone derivative as a mixture of two conformers in solution. Further we investigated the stereoelectronic influence of substituents at the ortho position on the pyrimidine ring with respect to the carbonyl group, as well as the electronic effects of pyrimidine by changing it to phenyl. The conformer equilibrium was attributed to the decoplanarization of the aromatic ring and carbonyl group (generated by an ortho-alkyl group) and/or the electron withdrawing character of the pyrimidine ring. Both effects increased the rotational barrier of the C-N amide bond, as verified by the ΔG≠ values calculated from dynamic NMR. As far as we know, it is the first description of aryl-NAH compounds presenting two CO-NH bond-related conformations.

PYRIMIDINE CARBOXYLIC ACID DERIVATIVES AND USE THEREOF

The invention relates to pyrimidine carboxylic acid derivatives of formula (I), to methods for the production thereof, to their use for treating and/or preventing diseases, and their use for producing medicaments for treating and/or preventing diseases, p