2965-90-4

Basic information

• Product Name: DIETHYL 4-FLUOROPHENYL MALONATE
• Synonyms: Diethyl 2-(4-fluorophenyl)malonate;2-(4-FLUOROPHENYL)-PROPANEDIOIC ACID, 1,3-DIETHYL ESTER;2-(4-Fluorophenyl)-malonic acid diethylester;Diethyl 2-(4-fluorophenyl)propane-1,3-dioate
• CAS NO: 2965-90-4
• Molecular Formula: C₁₃H₁₅FO₄
• Molecular Weight: 254.2542032
• Mol File: 2965-90-4.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 302.9 °C at 760 mmHg
• Flash Point: 132.6 °C
• Appearance: /
• Density: 1.173±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 0.000961mmHg at 25°C
• Refractive Index: 1.4774 (589.3 nm 20℃)
• PKA: 11.53±0.46(Predicted)
• CAS DataBase Reference: DIETHYL 4-FLUOROPHENYL MALONATE(CAS DataBase Reference)
• NIST Chemistry Reference: DIETHYL 4-FLUOROPHENYL MALONATE(2965-90-4)
• EPA Substance Registry System: DIETHYL 4-FLUOROPHENYL MALONATE(2965-90-4)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 2965-90-4(Hazardous Substances Data)

Usage

General Description

Diethyl 4-fluorophenyl malonate is a chemical compound with the molecular formula C13H13FO4. It is an ester formed from the condensation of diethyl malonate and 4-fluorophenol. Diethyl 4-fluorophenyl malonate is used as an intermediate in the synthesis of pharmaceuticals, agrochemicals, and other organic compounds. Its 4-fluorophenyl group makes it a valuable building block for the production of various fluorinated organic compounds. Diethyl 4-fluorophenyl malonate has potential applications in medicinal chemistry and drug development due to its fluorine substitution, which can enhance the biological activity and metabolic stability of the resulting compounds. Diethyl 4-fluorophenyl malonate may also be used in research and development studies in the field of organic chemistry.

InChI:InChI=1/C13H15FO4/c1-3-17-12(15)11(13(16)18-4-2)9-5-7-10(14)8-6-9/h5-8,11H,3-4H2,1-2H3

Upstream product

• 105-58-8 Diethyl carbonate 
• 587-88-2 ethyl 2-(4-fluorophenyl)acetate 
• 448-59-9 tris(4-fluorophenyl)boroxine 
• 105-53-3 diethyl malonate 
• 405-50-5 p-Fluorophenylacetic acid 
• 459-04-1 4-Fluorophenylacetyl chloride 
• 352-34-1 4-fluoro-1-iodobenzene 
• 623-49-4 ethyl cyanoformate 
• 460-00-4 1-Bromo-4-fluorobenzene 

Downstream Products

• 95724-76-8 2-(4-fluorophenyl)propane-1,3-diamine 
• 957131-33-8 N-[3-amino-2-(4-fluorophenyl)propyl]acetamide 
• 957131-25-8 (R)-(-)-allyl (3-amino-2-(4-fluorophenyl)propyl)carbamate 
• 957131-20-3 2-(4-fluorophenyl)propane-1,3-diazide 
• 957131-16-7 2-(4-fluorophenyl)propane-1,3-diyl dimethanesulfonate 

Relevant articles and documents

Radical Addition Enables 1,2-Aryl Migration from a Vinyl-Substituted All-Carbon Quaternary Center

An efficient method for photocatalytic perfluoroalkylation of vinyl-substituted all-carbon quaternary centers involving 1,2-aryl migration has been developed. The rearrangement reactions use fac-Ir(ppy)3, visible light and commercially available fluoroalkyl halides and can generate valuable multisubstituted perfluoroalkylated compounds in a single step that would be challenging to prepare by other methods. Mechanistically, the photoinduced alkyl radical addition to an alkene leads to the migration of a vicinal aryl substituent from its adjacent all-carbon quaternary center with the concomitant generation of a C-radical bearing two electron-withdrawing groups that is further reduced by a hydrogen donor to complete the domino sequence.

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.

OXIDATIVE COUPLING OF ARYL BORON REAGENTS WITH SP3-CARBON NUCLEOPHILES, AND AMBIENT DECARBOXYLATIVE ARYLATION OF MALONATE HALF-ESTERS VIA OXIDATIVE CATALYSIS

Described herein are methods of oxidative coupling of aryl boron reagents with sp3-carbon nucleophiles, and ambient decarboxylative arylation of malonate half-esters via oxidative catalysis.