2065-23-8

Basic information

• Product Name: Methyl phenoxyacetate
• Synonyms: METHYL PHENOXYACETATE;PHENOXYACETIC ACID METHYL ESTER;PHENOXY METHYL ACETATE;phenoxy-aceticacimethylester;Acetic acid, phenoxy-, methyl ester;Methyl（ethyl）phenoxyacetate;Phenoxyacetic acid methyl;Methyl phenoxyacetate,99%
• CAS NO: 2065-23-8
• Molecular Formula: C₉H₁₀O₃
• Molecular Weight: 166.17
• EINECS: 218-176-4
• Product Categories: C8 to C9;Carbonyl Compounds;Esters;Building Blocks;C8 to C9;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
• Mol File: 2065-23-8.mol
• Article Data: 58

Chemical Properties

• Melting Point: 245 °C
• Boiling Point: 243 °C(lit.)
• Flash Point: >230 °F
• Appearance: clear colorless liquid
• Density: 1.149 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0294mmHg at 25°C
• Refractive Index: n20/D 1.514(lit.)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: Methyl phenoxyacetate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl phenoxyacetate(2065-23-8)
• EPA Substance Registry System: Methyl phenoxyacetate(2065-23-8)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• TSCA: T
• Hazardous Substances Data: 2065-23-8(Hazardous Substances Data)

Usage

Chemical Properties

Methyl phenoxyacetate, when the temperature ≥ 30°C is a clear colorless to slightly yellow liquid; at < 30°C is a white solid. It can be used as disinfectant or pharmaceutical intermediate or pesticide intermediate.

Uses

Methyl phenoxyacetate (MPOA) was used as an acylating agent in the synthesis of loracarbef, a carbacephalosporin antibiotic.

Preparation

synthesis of methyl phenoxyacetate: methyl bromoacetate (10 mL, 105.6 mmol) and phenol (9.9380 g, 105.6 mmol) were dissolved in 250 mL of acetone; K2CO3 (21.89 g, 158 mmol) and KI (5 g, 30 mmol) were added and the mixture heated to reflux with stirring overnight. The mixture was filtered and the resultant solution concentrated in vacuo. Deionized water (200 mL) was added. The reaction mixture was extracted with 50 mL ethyl acetate three times. The combined ethyl acetate layers were washed with brine, dried over MgSO4, and filtered. All ethyl acetate was removed in vacuo, resulting in a slightly yellow liquid (80% yield).

InChI:InChI=1/C9H10O3/c1-11-9(10)7-12-8-5-3-2-4-6-8/h2-6H,7H2,1H3

Upstream product

• 67-56-1 methanol 
• 122-59-8 2-phenoxyacetic acid 
• 21119-50-6 2-diazo-1-phenylethan-1-one 
• 96-34-4 methyl chloroacetate 
• 108-95-2 phenol 
• 621-88-5 phenoxyacetamide 
• 77-78-1 dimethyl sulfate 
• 1746-13-0 allyl phenyl ether 
• 19513-78-1 1-(4-methoxy-phenyl)-2-phenoxy-ethanone 
• 112445-76-8 4-methoxyphenyl 2-phenoxyacetate 
• 139-02-6 sodium phenoxide 
• 96-35-5 glycolic acid methyl ester 
• 74-88-4 methyl iodide 
• 594-09-2 trimethylphosphane 

Downstream Products

• 859967-81-0 2-(3,4-dimethoxy-phenyl)-4-phenoxy-acetoacetonitrile 
• 24483-61-2 (4-chloroacetyl-phenoxy)-acetic acid 
• 18045-26-6 1-phenoxy-2,4-pentanedione 
• 18861-15-9 N-benzyl-2-phenoxyacetamide 
• 107940-14-7 1-Methoxy-2-phenoxy-1-(trimethylsiloxy)ethen 
• 107940-15-8 2-Phenoxy-2-(trimethylsilyl)ethansaeure-methylester 
• 73257-33-7 (Z)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-((E)-(S)-3-hydroxy-4-methoxycarbonyl-4-phenoxy-but-1-enyl)-cyclopentyl]-hept-5-enoic acid methyl ester 
• 73257-33-7 16ξ-carbomethoxy-16-phenoxy-17,18,19,20-tetranorprostaglandin F_2α methyl ester 
• 40665-68-7 dimethyl (3-phenoxy-2-oxopropyl)phosphonate 
• 134245-04-8 [(2R,3S)-2-(2-Furan-2-yl-ethyl)-4-oxo-3-(2-phenoxy-acetylamino)-azetidin-1-yl]-acetic acid 
• 131533-62-5 [(2R,3S)-2-(2-Furan-2-yl-ethyl)-4-oxo-3-(2-phenoxy-acetylamino)-azetidin-1-yl]-acetic acid methyl ester 
• 80791-03-3 (4-Henicosafluorodecyl-phenoxy)-acetic acid methyl ester 
• 80791-02-2 (3-Henicosafluorodecyl-phenoxy)-acetic acid methyl ester 
• 80791-01-1 (2-Henicosafluorodecyl-phenoxy)-acetic acid methyl ester 

Relevant articles and documents

Phenoxyacetohydrazones against Trypanosoma cruzi

Herein, we reported the design, synthesis, antitrypanosomal and cytotoxic evaluation of a new phenoxyacetohydrazones series. All derivatives were assayed against bloodstream trypomastigote forms of T. cruzi (Y strain) and intracellular amastigotes using the model of L-929 cells infected with trypomastigotes of the Tulahuen strain. Compound (E)-N′-(3.4-dihydroxybenzylidene)-2-phenoxyacetohydrazide (11) showed activity against trypomastigotes (IC50/24 h = 10.3 μM) equivalent to that of benznidazole and with selectivity index (SI) = 46. Against infected cultures, (E)-N′-((5-nitrofuran-2-yl) methylene)-2-phenoxyacetohydrazide (19) was active at the nanomolar range (IC50/96 h = 40 nM), being about 38-fold more active than the standard drug and with SI equal to 2500. Thus, derivatives 11 and 19 could be considered a good prototypes for the development of new candidates for Chagas disease therapy. [Figure not available: see fulltext.]

Novel phenolic Mannich base derivatives: synthesis, bioactivity, molecular docking, and ADME-Tox Studies

In this study, it was aimed to synthesize novel molecules containing potential biological active phenolic Mannich base moiety and evaluate the inhibition properties against α-glycosidase (α-Gly) and acetylcholinesterase (AChE). For this purpose, phenolic aldehydes (1–3) were synthesized from 4-hydroxy-3-methoxy benzaldehyde (vanillin) according to the Mannich Reaction. Five different carboxylic acid hydrazides (4a-e) were synthesized from esters obtained from carboxylic acids. Fifteen Schiff base derivatives (5a-e, 6a-e, and 7a-e) were synthesized from the condensation reaction of compounds 1–3 with 4a-e. In this work, a series of novel Schiff bases from Phenolic Mannich bases (5a-e, 6a-e, and 7a-e) were tested toward α-Gly and AChE enzymes. Compounds 5a-e, 6a-e, and 7a-e showed Kis in ranging of 341.36 ± 31.84–904.76 ± 93.56?nM on AChE and 176.27 ± 22.87—621.77 ± 69.98?nM on α-glycosidase. Finally, novel compounds were found using molecular docking method to calculate the biological activity of these bases against many enzymes. The enzymes used in these calculations are acetylcholinesterase and α-glycosidase, respectively. Molecule 6b is more effective and active than other molecules with a docking score parameter value of ? 8.77 against AChE enzyme and 6d is more effective and active than other molecules with a docking score parameter value of ? 4.94 against α-Gly enzyme. After calculating the biological activities of novel compounds, ADME/T analysis parameters were examined to calculate the future drug use properties.

Synthesis and anti-coronavirus activity of a series of 1-thia-4-azaspiro[4.5]decan-3-one derivatives

A series of 1-thia-4-azaspiro[4.5]decan-3-ones bearing an amide group at C-4 and various substitutions at C-2 and C-8 were synthesized and evaluated against human coronavirus and influenza virus. Compounds 7m, 7n, 8k, 8l, 8m, 8n, and 8p were found to inhibit human coronavirus 229E replication. The most active compound was N-(2-methyl-8-tert-butyl-3-oxo-1-thia-4-azaspiro[4.5]decan-4-yl)-3-phenylpropanamide (8n), with an EC50 value of 5.5 μM, comparable to the known coronavirus inhibitor, (Z)-N-[3-[4-(4-bromophenyl)-4-hydroxypiperidin-1-yl]-3-oxo-1-phenylprop-1-en-2-yl]benzamide (K22). Compound 8n and structural analogs were devoid of anti-influenza virus activity, although their scaffold is shared with a previously discovered class of H3 hemagglutinin-specific influenza virus fusion inhibitors. These findings point to the 1-thia-4-azaspiro[4.5]decan-3-one scaffold as a versatile chemical structure with high relevance for antiviral drug development.