262609-07-4

Basic information

• Product Name: DIETHYL 2,4,6-TRIFLUOROPHENYL MALONATE
• Synonyms: DIETHYL 2,4,6-TRIFLUOROPHENYL MALONATE;DIETHYL 2-(2,4,6-TRIFLUOROPHENYL)MALONATE;2-(2,4,6-Trifluorophenyl)malonic acid diethyl ester;1,3-diethyl 2-(2,4,6-trifluorophenyl)propanedioate;Diethyl 2-(2,4,6-trifluorophenyl)propane-1,3-dioate
• CAS NO: 262609-07-4
• Molecular Formula: C₁₃H₁₃F₃O₄
• Molecular Weight: 290.24
• Mol File: 262609-07-4.mol
• Article Data: 10

Chemical Properties

• Melting Point: 46-49℃
• Boiling Point: 283.7 °C at 760 mmHg
• Flash Point: 121.5 °C
• Appearance: /
• Density: 1.289 g/cm³
• Vapor Pressure: 0.00311mmHg at 25°C
• Refractive Index: 1.467
• CAS DataBase Reference: DIETHYL 2,4,6-TRIFLUOROPHENYL MALONATE(CAS DataBase Reference)
• NIST Chemistry Reference: DIETHYL 2,4,6-TRIFLUOROPHENYL MALONATE(262609-07-4)
• EPA Substance Registry System: DIETHYL 2,4,6-TRIFLUOROPHENYL MALONATE(262609-07-4)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 262609-07-4(Hazardous Substances Data)

Usage

General Description

DIETHYL 2,4,6-TRIFLUOROPHENYL MALONATE is a chemical compound with the molecular formula C13H11F3O4. It is characterized by the presence of a trifluorophenyl moiety and malonate ester group. DIETHYL 2,4,6-TRIFLUOROPHENYL MALONATE is commonly used in organic synthesis as a precursor for various pharmaceuticals and agrochemicals. It has been reported to exhibit insecticidal and herbicidal properties, making it suitable for use in the agricultural industry. Additionally, it serves as a useful intermediate in the production of other fluorinated compounds. However, its specific applications and properties may vary depending on the context in which it is used.

InChI:InChI=1/C13H13F3O4/c1-3-19-12(17)11(13(18)20-4-2)10-8(15)5-7(14)6-9(10)16/h5-6,11H,3-4H2,1-2H3

Upstream product

• 918418-36-7 diethyl 2-chloro-2-(2',4',6'-trifluorophenyl)malonate 
• 918419-00-8 3,3-dichloro-2-(2,4,6-trifluoro-phenyl)-acrylicacidethylester 
• 141-52-6 sodium ethanolate 
• 64-19-7 acetic acid 
• 123-91-1 1,4-dioxane 
• 2367-76-2 2,4,6-trifluorobromobenzene 
• 105-53-3 diethyl malonate 

Downstream Products

• 849600-53-9 5-(2,4,6-trifluorophenyl)pyrimidine-2,4,6-triol 
• 918419-01-9 Ethyl 3,3-Diethoxy-2-(2',4',6'-Trifluorophenyl)Acrylate 
• 1584642-07-8 (S)-5-chloro-6-(2,6-difluoro-4-(3-((2,2,2-trifluoroethyl)amino)propoxy)phenyl)-N-(1,1,1-trifluoropropan-2-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine 
• 249648-16-6 5-chloro-N-[(1S)-2,2,2-trifluoro-1-methylethyl]-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine-7-amine 
• 1619924-38-7 C₂₄H₂₁ClF₅N₅O₄S 
• 1619924-31-0 (S)-5-azido-6-(2,4,6-trifluorophenyl)-N-(1,1,1-trifluoropropan-2-yl)[1,2,4]triazolo[1,5-a]pyrimidin-7-amine 
• 585535-51-9 4,6-dichloro-2-(pyridin-2-yl)-5-(2,4,6-trifluorophenyl)pyrimidine 
• 849600-51-7 4,6-dichloro-2-(pyrazin-2-yl)-5-(2,4,6-trifluorophenyl)pyrimidine 
• 585535-50-8 C₁₅H₈F₃N₃O₂ 
• 849600-52-8 2-pyrazin-2-yl-5-(2,4,6-trifluorophenyl)pyrimidine-4,6-diol 
• 1584642-13-6 6-chloro-5-(4-(3-(dimethylamino)propoxy)-2,6-difluorophenyl)-2-(pyridin-2-yl)-N-(2,2,2-trifluoroethyl)pyrimidin-4-amine 
• 585536-05-6 6-chloro-2-(pyridin-2-yl)-N-(2,2,2-trifluoroethyl)-5-(2,4,6-trifluorophenyl)pyrimidin-4-amine 
• 849600-02-8 6-chloro-2-(pyrazin-2-yl)-N-(2,2,2-trifluoroethyl)-5-(2,4,6-trifluorophenyl)pyrimidin-4-amine 
• 1584642-06-7 (S)-5-chloro-6-(2,6-difluoro-4-(3-(phenylamino)propoxy)phenyl)-N-(1,1,1-trifluoropropan-2-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine 

Relevant articles and documents

Evaluation of the Structure-Activity Relationship of Microtubule-Targeting 1,2,4-Triazolo[1,5- a]pyrimidines Identifies New Candidates for Neurodegenerative Tauopathies

Studies in tau and Aβ plaque transgenic mouse models demonstrated that brain-penetrant microtubule (MT)-stabilizing compounds, including the 1,2,4-triazolo[1,5-a]pyrimidines, hold promise as candidate treatments for Alzheimer's disease and related neurodegenerative tauopathies. Triazolopyrimidines have already been investigated as anticancer agents; however, the antimitotic activity of these compounds does not always correlate with stabilization of MTs in cells. Indeed, previous studies from our laboratories identified a critical role for the fragment linked at C6 in determining whether triazolopyrimidines promote MT stabilization or, conversely, disrupt MT integrity in cells. To further elucidate the structure-activity relationship (SAR) and to identify potentially improved MT-stabilizing candidates for neurodegenerative disease, a comprehensive set of 68 triazolopyrimidine congeners bearing structural modifications at C6 and/or C7 was designed, synthesized, and evaluated. These studies expand upon prior understanding of triazolopyrimidine SAR and enabled the identification of novel analogues that, relative to the existing lead, exhibit improved physicochemical properties, MT-stabilizing activity, and pharmacokinetics.

Method for the production of substituted 2-aryl malonic acid esters

The present invention relates to a process for preparing substituted 2-arylmalonic esters of the general formula I in which R is C1-C6-alkyl or C1-C4-alkoxy-C1-C4-alkyl; Ar is phenyl or a heteroaromatic 5- or 6-membered ring; where each carbon atom present in the radicals mentioned above optionally carries a substituent RA; RA is F, Cl, CN, NO2, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, etc., or two adjacent substituents RA together with the carbon atoms to which they are attached form a ring; and where a malonic ester is reacted with a base and an aryl bromide in the presence of a copper salt, which comprises employing from 0.1 to 0.65 molar equivalents of the base per molar equivalent of the malonic ester.

Method for Production of Substituted Phenylmalonate Esters, Novel Phenylmalonate Esters and Use Thereof

A process for preparing substituted phenylmalonic esters of the formula in which R is alkyl and Q is halogen, alkyl, alkoxy, haloalkyl or haloalkoxy and the index m is an integer from 1 to 5, where the groups Q can be identical or different if the index m is greater than 1, comprising steps A), B) and C): A) reaction of compounds of the formula II, in which the variables are as defined for formula I to give compounds of the formula III, B) conversion of the compounds of the formula III into ketals of the formula IV in which R′ is C1-C4-alkyl or benzyl, C) hydrolysis of the compounds of the formula IV to give compounds of the formula I; novel phenylmalonic ester derivatives, and their use as intermediates.