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| | Triethyl 2-fluoro-2-phosphonoacetate Basic information |
| | Triethyl 2-fluoro-2-phosphonoacetate Chemical Properties |
| Boiling point | 75 °C0.01 mm Hg(lit.) | | density | 1.194 g/mL at 25 °C(lit.) | | refractive index | n20/D 1.425(lit.) | | Fp | 165 °F | | storage temp. | Keep in dark place,Inert atmosphere,Room temperature | | form | clear liquid | | color | Colorless to Almost colorless | | Specific Gravity | 1.194 | | BRN | 1912161 | | InChI | InChI=1S/C8H16FO5P/c1-4-12-8(10)7(9)15(11,13-5-2)14-6-3/h7H,4-6H2,1-3H3 | | InChIKey | FVPISMANESAJQZ-UHFFFAOYSA-N | | SMILES | C(OCC)(=O)C(P(OCC)(OCC)=O)F | | CAS DataBase Reference | 2356-16-3(CAS DataBase Reference) |
| Hazard Codes | Xi,F | | Risk Statements | 36/37/38 | | Safety Statements | 26-36-37/39 | | WGK Germany | 3 | | F | 10-21 | | Hazard Note | Irritant | | HazardClass | IRRITANT, FLAMMABLE | | HS Code | 29319090 | | Storage Class | 10 - Combustible liquids | | Hazard Classifications | Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| | Triethyl 2-fluoro-2-phosphonoacetate Usage And Synthesis |
| Chemical Properties | clear colorless liquid | | Uses | Reactant for:
- Diels-Alder reactions
- Biosynthesis of terpene
- Stereoselective synthesis of unsaturated esters, fluorides and nitriles from the reactions of aldehydes and ketones using Wadsworth-Emmons phosphonates
- Synthesis of quinolones
- Horner-Wadsworth-Emmons asymmetric hydration
- Addition reactions and the subsequent application to click chemistry
- Asymmetric intermolecular Stetter reactions
| | Synthesis Reference(s) | The Journal of Organic Chemistry, 60, p. 4730, 1995 DOI: 10.1021/jo00120a014 | | reaction suitability | reaction type: C-C Bond Formation | | Synthesis | Ethyl 2-bromo-2-fluoroacetate (5.0 g, 27 mmol) was mixed with triethyl phosphite (13 mL) and the reaction was heated at 130°C for 23 hours. After completion of the reaction, the resulting mixture was distilled under reduced pressure (1.4 mbar, 75-110°C) to afford triethyl 2-fluoro-2-phosphonoacetate, the product being a pale yellow oil (6.0 g, 92% yield). | | References | [1] Phosphorus, Sulfur and Silicon and Related Elements, 2000, vol. 160, p. 195 - 205
[2] Patent: WO2017/100668, 2017, A1. Location in patent: Page/Page column 162
[3] Patent: WO2018/103058, 2018, A1. Location in patent: Page/Page column 161; 165-166; 339
[4] Journal of the American Chemical Society, 2007, vol. 129, # 15, p. 4536 - 4537
[5] Heterocycles, 2004, vol. 63, # 3, p. 699 - 706 |
| | Triethyl 2-fluoro-2-phosphonoacetate Preparation Products And Raw materials |
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