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| | Ethyl 2-(ethoxymethylene)-4,4,4-trifluoroacetoacetate Basic information |
| Product Name: | Ethyl 2-(ethoxymethylene)-4,4,4-trifluoroacetoacetate | | Synonyms: | ETHYL 3-ETHOXY-2-(2,2,2-TRIFLUOROACETYL)ACRYLATE;ETHYL 2-(ETHOXYMETHYLENE)-4,4,4-TRIFLUORO-3-OXOBUTYRATE;ETHYL 2-(ETHOXYMETHYLENE)-4,4,4-TRIFLUOROACETOACETATE;ETHYL ETHOXYMETHYLENE-3-OXO-4,4,4-TRIFLUOROBUTYRATE;ethyl 2-(ethoxymethylene)-4,4,4-trifluoro-3-oxobu;ETHYL 2-(ETHOXYMETHYLENE)-4,4,4-TRIFLUOR O-3-OXOBUTYRATE, 96%, CIS AND TRANS;ethyl 2-(ethoxymethylene)-4,4,4-trifluoro-3-oxobutyrate,mixture of cis and trans;Ethyl 2-(ethoxymethylene)-3-oxo-4,4,4-trifluorobutyrate 97% | | CAS: | 571-55-1 | | MF: | C9H11F3O4 | | MW: | 240.18 | | EINECS: | 611-474-9 | | Product Categories: | Small molecule;C8 to C9;Carbonyl Compounds;Esters | | Mol File: | 571-55-1.mol |  |
| | Ethyl 2-(ethoxymethylene)-4,4,4-trifluoroacetoacetate Chemical Properties |
| Boiling point | 80-82 °C1 mm Hg(lit.) | | density | 1.235 g/mL at 25 °C(lit.) | | refractive index | n20/D 1.429(lit.) | | Fp | 220 °F | | storage temp. | 2-8°C | | form | clear liquid | | Specific Gravity | 1.239 | | color | Light orange to Yellow to Green | | InChI | InChI=1S/C9H11F3O4/c1-3-15-5-6(8(14)16-4-2)7(13)9(10,11)12/h5H,3-4H2,1-2H3 | | InChIKey | XNGGOXOLHQANRB-WAYWQWQTSA-N | | SMILES | C(OCC)(=O)C(=COCC)C(=O)C(F)(F)F | | CAS DataBase Reference | 571-55-1(CAS DataBase Reference) |
| | Ethyl 2-(ethoxymethylene)-4,4,4-trifluoroacetoacetate Usage And Synthesis |
| Uses | Ethyl 2-(ethoxymethylene)-4,4,4-trifluoro-3-oxobutyrate may be employed as a starting reagent for the synthesis of 1-methyl-3-trifluoromethyl-1H-pyrazole-4- carboxylic acid. | | General Description | Ethyl 2-(ethoxymethylene)-4,4,4-trifluoro-3-oxobutyrate has been reported to participate in the microwave-assisted synthesis of ethyl 1-[4-(2,3,3-trichloroacrylamido)phenyl]-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate. | | Synthesis | General procedure for the synthesis of ethyl ethoxy-2-methylene trifluoroacetoacetate from triethyl orthoformate and ethyl trifluoroacetoacetate: ethyl 4,4,4-trifluoro-3-oxobutanoate (30 g, 162.9 mmol) was added to a solution of acetic anhydride (50 mL) containing triethoxymethane (72.4 g, 488.8 mmol). The reaction mixture was stirred continuously at 135 °C for 18 hours. Upon completion of the reaction, the brown mixture was concentrated to afford ethyl 2-(ethoxymethylene)-4,4,4-trifluoro-3-oxobutanoate (38 g, 97.1% yield), the product was a brown oil that could be used in subsequent reactions without further purification. The product was characterized by 1H NMR (400 MHz, CDCl3): δ 1.23-1.33 (m, 3H), 1.40 (dt, J = 14.18, 7.19 Hz, 3H), 4.19-4.36 (m, 4H), 7.66-7.87 (m, 1H). | | References | [1] Journal of medicinal chemistry, 2000, vol. 43, # 21, p. 3995 - 4004
[2] Patent: US2018/170909, 2018, A1. Location in patent: Paragraph 0824; 0825
[3] Patent: CN106432183, 2017, A. Location in patent: Paragraph 0031; 0032
[4] Patent: WO2016/151403, 2016, A1. Location in patent: Paragraph 00520
[5] Journal of Molecular Structure, 2018, vol. 1171, p. 631 - 638 |
| | Ethyl 2-(ethoxymethylene)-4,4,4-trifluoroacetoacetate Preparation Products And Raw materials |
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