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| | Diethyl bromodifluoromethanephosphonate Basic information |
| | Diethyl bromodifluoromethanephosphonate Chemical Properties |
| Boiling point | 40-41 °C/0.05 mmHg (lit.) | | density | 1.503 g/mL at 25 °C (lit.) | | refractive index | n20/D 1.417(lit.) | | Fp | >230 °F | | storage temp. | Keep in dark place,Inert atmosphere,Room temperature | | solubility | Chloroform, Ethyl Acetate | | form | liquid | | Specific Gravity | 1.503 | | color | colorless | | Water Solubility | Not miscible or difficult to mix in water. | | BRN | 1944045 | | InChI | InChI=1S/C5H10BrF2O3P/c1-3-10-12(9,11-4-2)5(6,7)8/h3-4H2,1-2H3 | | InChIKey | QRADKVYIJIAENZ-UHFFFAOYSA-N | | SMILES | P(=O)(OCC)(OCC)C(F)(F)Br | | CAS DataBase Reference | 65094-22-6(CAS DataBase Reference) |
| Hazard Codes | Xi | | Risk Statements | 21/22-36/38-38-36 | | Safety Statements | 26-36/37/39-60-37-23 | | RIDADR | 3278 | | WGK Germany | 3 | | Hazard Note | Irritant | | TSCA | No | | HazardClass | IRRITANT, IRRITANT-HARMFUL | | PackingGroup | III | | HS Code | 29319090 | | Storage Class | 10 - Combustible liquids |
| | Diethyl bromodifluoromethanephosphonate Usage And Synthesis |
| Uses | Efficient difluoroalkylation of aryl boronic acids via palladium catalysis. Novel, moisture-stable bromodifluoromethylated phosphonate, ester, and amide. Efficient coupling with aryl boronic acids via Pd catalysis. | | Uses | Diethyl (bromodifluoromethyl)phosphonate is used as a reactant for the preparation of phosphopeptide mimetic prodrugs targeted to Src homology 2 (SH2) domain of signal transducer and activator of transcription 3 (Stat3), synthesis of Mycobacterium tuberculosis protein tyrosine phosphatase inhibitory difluoromethylphosphonic acid derivatives via multi step synthesis with Suzuki coupling and resolution as key steps and P-C bond cleavage on basic hydrolysis. | | Synthesis Reference(s) | The Journal of Organic Chemistry, 49, p. 3437, 1984 DOI: 10.1021/jo00192a056 | | reaction suitability | reaction type: C-C Bond Formation | | Synthesis | Dibromodifluoromethane (209.8 g, 1 mol) was slowly added dropwise to a solution of triethyl phosphite (153.5 g, 0.925 mol) in anhydrous ether (450 mL) equipped with a magnetic stirrer under nitrogen protection. After the dropwise addition, the reaction system was slowly warmed to room temperature and subsequently heated to reflux for 20 hours. Upon completion of the reaction, the volatile solvent was removed by distillation under reduced pressure and the fraction with a boiling point of 50-52 °C (1 mmHg) was collected to afford the colorless liquid product diethyl (bromodifluoromethyl) phosphonate (256.3 g, 96% yield). The structure of the product was confirmed by 1H NMR (CDCl3): δ 4.35 (m, 4H), 1.35 (m, 6H); 13C NMR (CDCl3): δ 122.9, 119.8, 118.6, 115.4, 114.2, 111.1, 66.59, 66.50, 16.56, 16.48. | | References | [1] Journal of Organometallic Chemistry, 1997, vol. 529, # 1-2, p. 267 - 278
[2] Phosphorus, Sulfur and Silicon and Related Elements, 1997, vol. 122, p. 247 - 259
[3] Patent: US2004/225146, 2004, A1. Location in patent: Page 4
[4] Journal of Fluorine Chemistry, 2011, vol. 132, # 10, p. 815 - 828
[5] Patent: WO2006/78698, 2006, A1. Location in patent: Page/Page column 64-65 |
| | Diethyl bromodifluoromethanephosphonate Preparation Products And Raw materials |
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