Dimethyl acetylmethylphosphonate CAS 4202-14-6
Dimethyl acetylmethylphosphonate Basic information
| Product Name: | Dimethyl acetylmethylphosphonate |
| Synonyms: | PHOSPHONIC ACID, (2-OXOPROPYL)-, DIMETHYL ESTER;LABOTEST-BB LT00847718;DIMETHYL (2-OXOPROPYL)PHOSPHONATE;DIMETHYL ACETONYLPHOSPHONATE;DIMETHYL ACETYLMETHYLPHOSPHONATE;Acetylmethylphosphonic acid dimethyl ester~Dimethyl acetonylphosphonate~Dimethyl (2-oxopropyl)phosphonate;Dimethyl(2-oxopropyl)phosph;Dimethylacetylmethylphosphonate,[Acetylmethylphosphonicaciddimethylester |
| CAS: | 4202-14-6 |
| MF: | C5H11O4P |
| MW: | 166.11 |
| EINECS: | 224-110-5 |
| Product Categories: | Horner-Emmons Reaction;Synthetic Organic Chemistry;Wittig & Horner-Emmons Reaction |
| Mol File: | 4202-14-6.mol |
Dimethyl acetylmethylphosphonate Chemical Properties
| Boiling point | 76-79 °C3 mm Hg(lit.) |
| density | 1.202 g/mL at 25 °C(lit.) |
| refractive index | n |
| Fp | 200 °F |
| storage temp. | Keep in dark place,Sealed in dry,Room Temperature |
| solubility | Difficult to mix. |
| form | Liquid |
| color | Clear colorless to light brown |
| BRN | 1766218 |
| InChI | InChI=1S/C5H11O4P/c1-5(6)4-10(7,8-2)9-3/h4H2,1-3H3 |
| InChIKey | UOWIYNWMROWVDG-UHFFFAOYSA-N |
| SMILES | P(CC(=O)C)(=O)(OC)OC |
| CAS DataBase Reference | 4202-14-6(CAS DataBase Reference) |
| NIST Chemistry Reference | Dimethyl (2-oxopropyl)phosphonate(4202-14-6) |
Safety Information
| Hazard Codes | Xi |
| Safety Statements | 23-24/25 |
| WGK Germany | 3 |
| F | 10 |
| Hazard Note | Irritant |
| HS Code | 29310095 |
| Storage Class | 10 - Combustible liquids |
| Chemical Properties | CLEAR COLOURLESS TO LIGHT BROWN LIQUID |
| Uses | Dimethyl acetylmethylphosphonate is a Reagent used together with tosyl azide in a one-pot alkynylation of aldehydes. |
| Synthesis Reference(s) | Tetrahedron Letters, 17, p. 2829, 1976 DOI: 10.1016/S0040-4039(01)85513-1 |
| reaction suitability | reaction type: C-C Bond Formation |
| Synthesis | 78-95-5 121-45-9 4202-14-6 General procedure for the synthesis of dimethyl acetone-based phosphonate from chloroacetone and trimethoxyphosphine: a dry and clean 500 mL coil was heated to 135 °C. 1000 g (0.7 eq., 10.81 mol) of chloroacetone (boiling point 117 to 119 °C at standard atmospheric pressure) was placed in charge bottle A and diluted with 4000 g of toluene. 1878 g (1.0 eq., 15.13 mol) of trimethoxyphosphine (boiling point at 112°C at standard atmospheric pressure) was placed in charge bottle B and diluted with 3122 g of toluene. After the temperature was stabilized, batch pumping of the chloroacetone-toluene solution in Bottle A and the trimethoxyphosphine-toluene solution in Bottle B was started at a rate of 12.5 g/min. The residence time of the reactants was 20 min, and the reaction pressure was maintained at 0.5 to 2.0 MPa. The reacted mixture was directly introduced into a thin-film evaporation unit, with a controlled pressure of 4 to 10 x 10^2 Pa and a temperature of between 60 and 70 °C. The reaction was carried out at a pressure of 4 to 10 x 10^2 Pa. Ultimately, 1230 g of dimethyl acetone-based phosphonate (boiling point 85 to 88 °C, 666 Pa) was obtained in 88% yield. |
| References | [1] Patent: CN107163079, 2017, A. Location in patent: Paragraph 0076; 0077; 0078 [2] Organic Letters, 2015, vol. 17, # 5, p. 1308 - 1311 [3] Journal of Medicinal Chemistry, 2013, vol. 56, # 21, p. 8765 - 8780 [4] Journal of the American Chemical Society, 1995, vol. 117, # 10, p. 2931 - 2932 [5] Organic and Biomolecular Chemistry, 2017, vol. 15, # 15, p. 3304 - 3309 |
Dimethyl acetylmethylphosphonate Preparation Products And Raw materials
| Raw materials | Acetone-->Acetonitrile-->Potassium iodide-->Trimethyl phosphite-->Chloroacetone-->Ethyl acetate-->Dimethyl methylphosphonate |
