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| | Ethyl trifluoropyruvate Basic information |
| Product Name: | Ethyl trifluoropyruvate | | Synonyms: | Ethyl trifluoropyruvate, Ethyl 2-oxo-3,3,3-trifluoropropionate;Threefluorideethylpyruvate;Ethyl 3,3,3-trifluoropyruvate 97%;ETHYL TRIFLUOROPYRUVATE;ETHYL 2-OXO-3,3,3-TRIFLUORO PROPIONATE;E-TFPA;3,3,3-TRIFLUORO-2-OXOPROPANOIC ACID ETHYL ESTER;RARECHEM AL BI 1300 | | CAS: | 13081-18-0 | | MF: | C5H5F3O3 | | MW: | 170.09 | | EINECS: | 603-440-7 | | Product Categories: | C2 to C5;Carbonyl Compounds;Esters | | Mol File: | 13081-18-0.mol |  |
| | Ethyl trifluoropyruvate Chemical Properties |
| Boiling point | 42 °C(lit.) | | density | 1.283 g/mL at 25 °C (lit.) | | vapor pressure | 12.49hPa at 25℃ | | refractive index | n20/D 1.341(lit.) | | Fp | 88 °F | | storage temp. | Inert atmosphere,2-8°C | | solubility | Miscible with dichloromethane. | | form | Liquid | | color | Clear colorless to pale yellow | | BRN | 2087388 | | Stability: | Moisture Sensitive | | InChI | InChI=1S/C5H5F3O3/c1-2-11-4(10)3(9)5(6,7)8/h2H2,1H3 | | InChIKey | KJHQVUNUOIEYSV-UHFFFAOYSA-N | | SMILES | C(OCC)(=O)C(=O)C(F)(F)F | | LogP | -0.05 | | CAS DataBase Reference | 13081-18-0(CAS DataBase Reference) |
| Hazard Codes | Xn,C,Xi | | Risk Statements | 10-22-36/37/38 | | Safety Statements | 26-37/39-16 | | RIDADR | UN 3272 3/PG 3 | | WGK Germany | 3 | | Hazard Note | Corrosive | | HazardClass | 3 | | PackingGroup | III | | HS Code | 29183000 | | Storage Class | 3 - Flammable liquids | | Hazard Classifications | Acute Tox. 4 Oral
Eye Irrit. 2
Flam. Liq. 3
Skin Irrit. 2
STOT SE 3 |
| | Ethyl trifluoropyruvate Usage And Synthesis |
| Chemical Properties | Clear pale yellow liquid | | Uses | Ethyl Trifluoropyruvate is used as a reagent in the preparation of potential biologically active compounds such as in the highly enantioselective organocatalytic hydroxyalkylation of indoles . | | Uses | Ethyl trifluoropyruvate acts as a building block in synthetic chemistry for the synthesis of fluorine containing compounds. It is also used as a reagent for the preparation of potential biologically active compounds like highly enantioselective organocatalytic hydroxyalkylation of indoles. | | Uses | Ethyl 3,3,3-trifluoropyruvate may be used in the preparation of N-heteroaryl(trifluoromethyl)hydroxyalkanoic acid esters. | | General Description | Ethyl 3,3,3-trifluoropyruvate is a trifluoromethylated compound. Enantioselective Friedel–Crafts alkylation of simple phenols and indoles with ethyl 3,3,3-trifluoropyruvate under different reaction conditions have been reported. | | Synthesis | To 58 mL (1.0 mL/mmol) of acetonitrile, 10 g (58 mmol, 1.0 eq) of ethyl 3,3,3-trifluorolactate was added and dissolved therein.Furthermore, 11 g (67 mmol, 1.2 eq) of NaClO.5H2O was added, followed by stirring at 20° C. for 30 minutes.As the reaction-terminated liquid was analyzed by 19F-NMR, conversion was 100%, and selectivity was 98%.To the reaction-terminated liquid, 0.38 g (1.5 mmol, 0.026 eq) of sodium thiosulfate pentahydrate was added, followed by stirring, thereby quenching the remaining oxidation agent.Furthermore, 0.33 g (3.9 mmol, 0.067 eq) of sodium hydrogencarbonate and 10 g (70 mmol, 1.2 eq) of sodium sulfate were added, followed by stirring and then removing solid matter by filtration.As the filtrate was quantified with internal standard method (internal standard substance: α,α,α-trifluorotoluene) by 19F-NMR, Ethyl trifluoropyruvate was contained by 56 mmol (quantitative yield: 97%).By a simple distillation (up to 48° C./0.5 kPa) of the filtrate, 7.6 g of Ethyl trifluoropyruvate was obtained. 19F-NMR purity was 99% (40 mmol), and the total yield was 69%. | | References | [1] Patent: US2018/50976, 2018, A1. Location in patent: Paragraph 0143; 0144; 0145; 0146; 0147; 0148; 0149; 0150 |
| | Ethyl trifluoropyruvate Preparation Products And Raw materials |
| Raw materials | Ethyl 3,3,3-trifluoro-2-hydroxy-propionate-->Sodium hypochlorite pentahydrate-->Acetonitrile | | Preparation Products | 4-(Trifluoromethyl)-alpha,alpha,alpha-trifluoroacetophenone-->2-(Trifluoromethyl)-5,7-dimethylquinoline-4-carboxylic acid-->4'-Cyano-2,2,2-trifluoroacetophenone-->5-Chloro-2-(trifluoromethyl)quinoline-4-carboxylic acid-->4-(Trifluoroacetyl)toluene-->6-Chloro-2-(trifluoromethyl)quinoline-4-carboxylic acid-->ethyl 3,3-difluoro-2-oxohex-5-enoate-->2-(Trifluoromethyl)-5-methylquinoline-4-carboxylic acid-->Ethyl 2-hydroxy-2-(trifluoromethyl)-4-methylpent-4-enoate 97-->AcetaMide, N-(4-chlorophenyl)-2,2,2-trifluoro- |
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