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Methyl phenoxyacetate

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CAS:2065-23-8
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Methyl phenoxyacetate manufacturers

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  • $5142.00 / 200Kg/Drum
  • 2021-11-02
  • CAS:2065-23-8
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  • 2021-07-13
  • CAS:2065-23-8
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Methyl phenoxyacetate Basic information
Product Name:Methyl phenoxyacetate
Synonyms:METHYL PHENOXYACETATE;PHENOXYACETIC ACID METHYL ESTER;PHENOXY METHYL ACETATE;Acetic acid, phenoxy-, methyl ester;Methyl(ethyl)phenoxyacetate;Phenoxyacetic acid methyl;Methyl phenoxyacetate,99%;phenoxy-aceticacimethylester
CAS:2065-23-8
MF:C9H10O3
MW:166.17
EINECS:218-176-4
Product Categories:Building Blocks;C8 to C9;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks;C8 to C9;Carbonyl Compounds;Esters
Mol File:2065-23-8.mol
Methyl phenoxyacetate Structure
Methyl phenoxyacetate Chemical Properties
Melting point 245 °C
Boiling point 243 °C (lit.)
density 1.149 g/mL at 25 °C (lit.)
refractive index n20/D 1.514(lit.)
Fp >230 °F
storage temp. Sealed in dry,Room Temperature
form clear liquid
color Colorless to Light orange to Yellow
Specific Gravity1.149
InChIInChI=1S/C9H10O3/c1-11-9(10)7-12-8-5-3-2-4-6-8/h2-6H,7H2,1H3
InChIKeyBZCKRPHEZOHHBK-UHFFFAOYSA-N
SMILESC(OC)(=O)COC1=CC=CC=C1
LogP1.410
CAS DataBase Reference2065-23-8(CAS DataBase Reference)
NIST Chemistry ReferenceAcetic acid, phenoxy-, methyl ester(2065-23-8)
EPA Substance Registry SystemAcetic acid, phenoxy-, methyl ester (2065-23-8)
Safety Information
Safety Statements 24/25
WGK Germany 3
TSCA TSCA listed
HS Code 29189900
Storage Class12 - Non Combustible Liquids
MSDS Information
ProviderLanguage
Methyl phenoxyacetate English
SigmaAldrich English
ACROS English
Methyl phenoxyacetate Usage And Synthesis
Chemical PropertiesMethyl 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.
UsesMethyl phenoxyacetate (MPOA) was used as an acylating agent in the synthesis of loracarbef, a carbacephalosporin antibiotic.
Preparationsynthesis 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).
Synthesis
Methyl chloroacetate

96-34-4

Phenol

108-95-2

Methyl phenoxyacetate

2065-23-8

9.4 g of phenol was dissolved in 100 μL of N,N-dimethylformamide and 11.9 g of methyl chloroacetate and 20.7 g of potassium carbonate were added sequentially. The reaction mixture was heated to 50 °C and stirred continuously for 12 h. The reaction process was monitored by thin layer chromatography (TLC). Upon completion of the reaction, 300 mL of ice water was added to the reaction system. The aqueous phase was extracted twice with 200 mL of ethyl acetate and the organic phases were combined. The organic phase was sequentially washed three times with 400 mL of saturated sodium chloride solution and dried over anhydrous sodium sulfate. After the solvent was removed by concentration under reduced pressure, the residue was purified by silica gel column chromatography (eluent ratio of petroleum ether:ethyl acetate=20:1) to afford 15.2 g of a light yellow oily product, methyl phenoxyacetate, in 92.0% yield.

References[1] Collection of Czechoslovak Chemical Communications, 1991, vol. 56, # 6, p. 1317 - 1332
[2] Synthetic Communications, 2005, vol. 35, # 13, p. 1759 - 1764
[3] Patent: CN108570028, 2018, A. Location in patent: Paragraph 0017-0018
[4] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 1, p. 132 - 140
[5] Asian Journal of Chemistry, 2013, vol. 25, # 11, p. 6189 - 6191
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