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5-Phenyl-isoxazole-3-carboxylic acid methyl ester

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5-Phenyl-isoxazole-3-carboxylic acid methyl ester Basic information
Product Name:5-Phenyl-isoxazole-3-carboxylic acid methyl ester
Synonyms:AKOS B024670;AKOS BBS-00002559;ART-CHEM-BB B024670;METHYL 5-PHENYLISOXAZOLE-3-CARBOXYLATE;METHYL 5-PHENYL-3-ISOXAZOLECARBOXYLATE;JR-7047, Methyl 5-phenylisoxazole-3-carboxylate, 97%;Methyl 5-phenyl-1,2-oxazole-3-carboxylate;3-Isoxazolecarboxylic acid, 5-phenyl-, Methyl ester
CAS:51677-09-9
MF:C11H9NO3
MW:203.19
EINECS:
Product Categories:
Mol File:51677-09-9.mol
5-Phenyl-isoxazole-3-carboxylic acid methyl ester Structure
5-Phenyl-isoxazole-3-carboxylic acid methyl ester Chemical Properties
Melting point 81°C
Boiling point 370.2±30.0 °C(Predicted)
density 1.204±0.06 g/cm3(Predicted)
storage temp. 2-8°C
form solid
pka-6.43±0.28(Predicted)
AppearanceWhite to off-white Solid
InChI1S/C11H9NO3/c1-14-11(13)9-7-10(15-12-9)8-5-3-2-4-6-8/h2-7H,1H3
InChIKeyXMPLCJOQBDGMKT-UHFFFAOYSA-N
SMILESCOC(=O)c1cc(on1)-c2ccccc2
Safety Information
Hazard Codes Xi
HazardClass IRRITANT
HS Code 2934999090
Storage Class11 - Combustible Solids
MSDS Information
5-Phenyl-isoxazole-3-carboxylic acid methyl ester Usage And Synthesis
UsesMethyl 5-Phenylisoxazole-3-carboxylate is a useful reagent for reactions with isoxazoles.
Synthesis
3-Butynoic acid, 4-phenyl-2-[(phenylmethoxy)imino]-, methyl ester, (2E)-

1313396-20-1

5-PHENYL-ISOXAZOLE-3-CARBOXYLIC ACID METHYL ESTER

51677-09-9

GENERAL METHODS: Alkyne oxime ether 1 (0.15 mmol) was dissolved in THF (5 mL) and phenol (28 mg, 0.3 mmol) and AgBF4 (5.8 mg, 0.03 mmol) were added sequentially. The reaction system was equipped with a drying tube (filled with silica gel) and heated to reflux at 50 °C in an oil bath. The reaction process was monitored by TLC with continuous stirring for 1-12 hours. After completion of the reaction, the reaction mixture was concentrated under reduced pressure. The residue was purified by preparative thin layer chromatography (unfolding reagent: hexane/ethyl acetate = 3-10:1) to afford the target product methyl 5-phenylisoxazole-3-carboxylate (3a and 3j). The physical properties and spectral data of the obtained compounds were in agreement with those reported in the literature.

References[1] Tetrahedron, 2011, vol. 67, # 25, p. 4612 - 4615
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