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| | tert-Butyl diethylphosphonoacetate Basic information |
| | tert-Butyl diethylphosphonoacetate Chemical Properties |
| Boiling point | 100-103 °C/1.5 mmHg (lit.) | | density | 1.074 g/mL at 25 °C (lit.) | | refractive index | n20/D 1.431(lit.) | | Fp | >230 °F | | storage temp. | Inert atmosphere,Room Temperature | | solubility | Chloroform (Slightly), Ethyl Acetate (Slightly) | | form | Liquid | | Specific Gravity | 1.074 | | color | Clear colorless | | Water Solubility | Not miscible or difficult to mix in water. | | BRN | 2050126 | | InChI | InChI=1S/C10H21O5P/c1-6-13-16(12,14-7-2)8-9(11)15-10(3,4)5/h6-8H2,1-5H3 | | InChIKey | NFEGNISFSSLEGU-UHFFFAOYSA-N | | SMILES | C(OC(C)(C)C)(=O)CP(OCC)(OCC)=O | | CAS DataBase Reference | 27784-76-5(CAS DataBase Reference) |
| Risk Statements | 36/38 | | Safety Statements | 26-36-24/25 | | WGK Germany | 3 | | HS Code | 29319090 | | Storage Class | 10 - Combustible liquids |
| | tert-Butyl diethylphosphonoacetate Usage And Synthesis |
| Chemical Properties | Clear colorless liquid | | Uses | tert-Butyl diethylphosphonoacetate is used as a reactant for preparation of hydroxymethylated dihydroxyvitamin D3 analogs via Wittig-Horner approach, as potential antitumor agents, synthesis of phosphopeptide mimetic prodrugs targeted to Src homology 2 (SH2) domain of signal transducer and activator of transcription 3 (Stat 3) and bicyclic triaminophosphine-promoted stereoselective synthesis of a,?-unsaturated esters, fluorides, and nitriles from aldehydes and ketones using Wadsworth-Emmons phosphonates | | Application | tert-Butyl diethylphosphonoacetate serves as an important intermediate in the synthesis of phosphonate derivatives, which are widely used in agrochemicals, pharmaceuticals, and materials science. | | reaction suitability | reaction type: C-C Bond Formation | | Synthesis | Triethyl phosphite (485 g) is warmed up to 90°C under N2 atmosphere in a three-necked round-bottomed flask, and /-butyl bromoacetate (541 g) is added dropwise into the system within 2 h. Then, the mixture is stirred at 90°C for around 4 hours and cooled to room temperature. The obtained mixture is distilled under vacuo to remove compounds with low boiling points, and the residue is collected as a colorless liquid tert-butyl diethylphosphonoacetate in 97 percent yield (680 g).
| | References | [1] Chemistry - A European Journal, 1999, vol. 5, # 4, p. 1218 - 1225
[2] Tetrahedron, 2009, vol. 65, # 49, p. 10192 - 10213
[3] Patent: WO2015/101554, 2015, A1. Location in patent: Page/Page column 17
[4] Patent: US2015/183764, 2015, A1. Location in patent: Paragraph 0039
[5] Journal of the American Chemical Society, 2007, vol. 129, # 47, p. 14818 - 14825 |
| | tert-Butyl diethylphosphonoacetate Preparation Products And Raw materials |
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