Ethyl 5-chloro-3-methyl-isoxazole-4-carboxylate

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Ethyl 5-chloro-3-methyl-isoxazole-4-carboxylate Basic information
Product Name:Ethyl 5-chloro-3-methyl-isoxazole-4-carboxylate
Synonyms:Ethyl 5-chloro-3-methyl-isoxazole-4-carboxylate;ethyl 5-chloro-3-Methyl-1,2-oxazole-4-carboxylate;4-Isoxazolecarboxylic acid, 5-chloro-3-methyl-, ethyl ester
CAS:3356-94-3
MF:C7H8ClNO3
MW:189.6
EINECS:
Product Categories:
Mol File:3356-94-3.mol
Ethyl 5-chloro-3-methyl-isoxazole-4-carboxylate Structure
Ethyl 5-chloro-3-methyl-isoxazole-4-carboxylate Chemical Properties
Boiling point 57 °C(Press: 0.3 Torr)
density 1.280±0.06 g/cm3(Predicted)
storage temp. 2-8°C
pka-5.09±0.50(Predicted)
AppearanceColorless to light yellow Liquid
Safety Information
MSDS Information
Ethyl 5-chloro-3-methyl-isoxazole-4-carboxylate Usage And Synthesis
UsesEthyl 5-Chloro-3-methyl-4-isoxazolecarboxylate is an intermediate used to prepare (difluorobutenylthio)-substituted heterocyclic or carbocyclic ring compounds as pesticides.
Synthesis
4-Isoxazolecarboxylic acid, 4,5-dihydro-3-methyl-5-oxo-, ethyl ester

16880-46-9

Ethyl 5-chloro-3-methyl-isoxazole-4-carboxylate

3356-94-3

General procedure for the synthesis of ethyl 5-chloro-3-methyl-3-isoazole-4-carboxylate from compound (CAS:16880-46-9): to compound 139a (3 g, 17.5 mmol) was added trichlorophosphorus (POCl3, 21.5 g, 140.2 mmol, 13 ml) in a single step. Theophylline (1.8 g, 17.5 mmol) was subsequently added. The reaction mixture was stirred at 110 °C for 24 h under the protection of nitrogen (N2). After completion of the reaction, ice water (15 ml) was added to the mixture to quench the reaction and the aqueous phase was extracted with ethyl acetate (EtOAc, 25 ml x 3). The organic layers were combined, washed with saturated brine, dried over anhydrous sodium sulfate (Na2SO4), and concentrated under reduced pressure to give the intermediate compound 139b (brown oil, 2.6 g, 13.7 mmol, yield: 78.2%).1H NMR (400 MHz, CDCl3) δ 4.36 (q, J = 7.1 Hz, 2H), 2.48 (s, 3H). 1.38 (t, J = 7.2Hz, 3H).

References[1] Patent: WO2018/64119, 2018, A1. Location in patent: Paragraph 0862
Ethyl 5-chloro-3-methyl-isoxazole-4-carboxylate Preparation Products And Raw materials
Raw materials4-Isoxazolecarboxylic acid, 4,5-dihydro-3-methyl-5-oxo-, ethyl ester-->Diethyl acetylmalonate
Tag:Ethyl 5-chloro-3-methyl-isoxazole-4-carboxylate(3356-94-3) Related Product Information
ethyl 5-bromo-3-methylisoxazole-4-carboxylate 5-chloro-3-methyl-1,2-oxazole-4-carbaldehyde (5-Chloro-3-methylisoxazol-4-yl)methanol 4-Isoxazolecarboxylic acid, 5-chloro-3-methyl-, methyl ester 4-Isoxazolecarboxylic acid, 5-chloro-, ethyl ester Ethyl 3-methylisoxazole-4-carboxylate