7550-03-0

Basic information

• Product Name: ethyl 4-fluorophenylglycolate
• Synonyms: α-Hydroxy-4-fluorobenzeneacetic acid ethyl ester;ethyl 2-(4-fluorophenyl)-2-hydroxyacetate;Ethyl (4-fluorophenyl)(hydroxy)acetate;ethyl 4-fluorophenylglycolate;4-Fluoro-α-hydroxybenzeneacetic acid ethyl ester
• CAS NO: 7550-03-0
• Molecular Formula: C₁₀H₁₁FO₃
• Molecular Weight: 198.1909432
• EINECS: 231-438-2
• Mol File: 7550-03-0.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 284.5°C at 760 mmHg
• Flash Point: 125.9°C
• Appearance: /
• Density: 1.229g/cm³
• Vapor Pressure: 0.00139mmHg at 25°C
• Refractive Index: 1.511
• CAS DataBase Reference: ethyl 4-fluorophenylglycolate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 4-fluorophenylglycolate(7550-03-0)
• EPA Substance Registry System: ethyl 4-fluorophenylglycolate(7550-03-0)

Safety Data

• Hazardous Substances Data: 7550-03-0(Hazardous Substances Data)

Usage

General Description

Ethyl 4-fluorophenylglycolate is an organic chemical compound with the formula C10H11FO3. It is a clear, colorless liquid with a fruity odor, and is commonly used in the synthesis of pharmaceuticals and fragrances. ethyl 4-fluorophenylglycolate is a ester, which means it is formed from the reaction between an alcohol and an acid, and it is commonly used as a flavoring agent in the food industry. Additionally, ethyl 4-fluorophenylglycolate is known for its potential applications in the development of new drugs, due to its pharmacological activity and ability to modify the taste, aroma, and functional properties of various products. However, it should be handled with caution as it may be harmful if ingested or inhaled, and can cause skin and eye irritation upon contact.

InChI:InChI=1/C10H11FO3/c1-2-14-10(13)9(12)7-3-5-8(11)6-4-7/h3-6,9,12H,2H2,1H3

Upstream product

• 924-44-7 glyoxylic acid ethyl ester 
• 1765-93-1 4-fluoroboronic acid 
• 64-17-5 ethanol 
• 32222-45-0 4-fluoromandelic acid 
• 462-06-6 fluorobenzene 
• 1813-94-1 ethyl 4-fluorobenzoylformate 
• 75-03-6 ethyl iodide 
• 102697-47-2 2-(4-fluorophenyl)-2-diazoacetic acid ethyl ester 
• 587-88-2 ethyl 2-(4-fluorophenyl)acetate 

Downstream Products

• 140213-26-9 1-{4-[6-Fluoro-2-(4-fluoro-phenyl)-benzofuran-3-yl]-piperidin-1-yl}-ethanone 
• 2251-76-5 2-(4-fluorophenyl)-2-oxoacetic acid 
• 1263869-19-7 ethyl 4-(2-ethoxy-1-(4-fluorophenyl)-2-oxoethoxy)but-2-enoate 
• 1263869-20-0 ethyl 4-(2-ethoxy-1-(4-fluorophenyl)-2-oxoethoxy)butanoate 
• 1263869-21-1 ethyl 2-(4-fluorophenyl)-3-oxotetrahydro-2H-pyran-4-carboxylate 
• 1263869-22-2 8-(4-fluorophenyl)-5,6-dihydro-1H-pyrano[3,4-d]pyrimidine-2,4(3H,5H)-dione 
• 1263869-18-6 2,4-dichloro-8-(4-fluorophenyl)-6,8-dihydro-5H-pyrano[3,4-d]pyrimidine 
• 1263869-23-3 2-chloro-N-ethyl-8-(4-fluorophenyl)-6,8-dihydro-5H-pyrano[3,4-d]pyrimidin-4-amine 
• 1263869-24-4 2-chloro-N-ethyl-8-(4-fluorophenyl)-N-methyl-6,8-dihydro-5H-pyrano[3,4-d]pyrimidin-4-amine 
• 712-52-7 α-bromo-4-fluorobenzeneacetic acid,ethyl ester 
• 1446252-34-1 (E)-ethyl 3-(2-(tert-butoxycarbonylamino)pyridin-4-yl)-2-(4-fluorophenyl) acrylate 
• 1446252-35-2 (E)-2-(4-fluorophenyl)-3-( pyridin-4-yl)acrylic acid 
• 1446252-37-4 (E)-ethyl 3-(2-aminopyridine-4-yl)-2-(4-fluorophenyl)acrylate 
• 1446252-38-5 (E)-ethyl 2-(4-fluorophenyl)-3-(2-(isopropylamino)pyridin-4-yl)acrylate 

Relevant articles and documents

Exploiting Cofactor Versatility to Convert a FAD-Dependent Baeyer–Villiger Monooxygenase into a Ketoreductase

Cyclohexanone monooxygenases (CHMOs) show very high catalytic specificity for natural Baeyer–Villiger (BV) reactions and promiscuous reduction reactions have not been reported to date. Wild-type CHMO from Acinetobacter sp. NCIMB 9871 was found to possess an innate, promiscuous ability to reduce an aromatic α-keto ester, but with poor yield and stereoselectivity. Structure-guided, site-directed mutagenesis drastically improved the catalytic carbonyl-reduction activity (yield up to 99 %) and stereoselectivity (ee up to 99 %), thereby converting this CHMO into a ketoreductase, which can reduce a range of differently substituted aromatic α-keto esters. The improved, promiscuous reduction activity of the mutant enzyme in comparison to the wild-type enzyme results from a decrease in the distance between the carbonyl moiety of the substrate and the hydrogen atom on N5 of the reduced flavin adenine dinucleotide (FAD) cofactor, as confirmed using docking and molecular dynamics simulations.

Discovery of novel 2-(3-phenylpiperazin-1-yl)-pyrimidin-4-ones as glycogen synthase kinase-3β inhibitors

We herein describe the results of further evolution of glycogen synthase kinase (GSK)-3β inhibitors from our promising compounds containing a 2-phenylmorpholine moiety. Transformation of the morpholine moiety into a piperazine moiety resulted in potent GSK-3β inhibitors. SAR studies focused on the phenyl moiety revealed that a 4-fluoro-2-methoxy group afforded potent inhibitory activity toward GSK-3β. Based on docking studies, new hydrogen bonding between the nitrogen atom of the piperazine moiety and the oxygen atom of the main chain of Gln185 has been indicated, which may contribute to increased activity compared with that of the corresponding phenylmorpholine analogues. Effect of the stereochemistry of the phenylpiperazine moiety is also discussed.

Azastilbenes: A cut-off to p38 MAPK inhibitors

Inhibitors with vicinal 4-fluorophenyl/4-pyridine rings on a five- or six-membered heterocyclic ring are known to inhibit the p38 mitogen-activated protein kinase (MAPK), which is a potential target for rheumatoid arthritis and several different types of cancer. Several substituted azastilbene-based compounds with vicinal 4-fluorophenyl/4-pyridine rings were designed using computational docking, synthesized, and evaluated in a cell-free radiometric p38α assay. The biochemical evaluation shows that the best inhibition (down to 110 nM) is achieved for azastilbene-based compounds having an isopropylamine substituent in the 2-position of the pyridine ring. The inhibition of p38 signaling in human breast cancer cells was observed for two of the compounds. The Royal Society of Chemistry 2013.