| Identification | More | [Name]
Dimethyl acetylmethylphosphonate | [CAS]
4202-14-6 | [Synonyms]
(2-OXOPROPYL)PHOSPHONIC ACID DIMETHYL ESTER
ACETONYLPHOSPHONIC ACID DIMETHYL ESTER
DIMETHYL (2-OXOPROPYL)PHOSPHONATE
DIMETHYL ACETONYLPHOSPHONATE
DIMETHYL ACETYLMETHYLPHOSPHONATE
LABOTEST-BB LT00847718
PHOSPHONIC ACID, (2-OXOPROPYL)-, DIMETHYL ESTER
Acetylmethylphosphonic acid dimethyl ester~Dimethyl acetonylphosphonate~Dimethyl (2-oxopropyl)phosphonate
Dimethyl(2-oxopropyl)phosph
Dimethylacetylmethylphosphonate,[Acetylmethylphosphonicaciddimethylester
Acetylmethylphosphonicaciddimethylester
Dimethylacetylmethylphosphonate,97+%
Dimethyl(2-oxopropyl)phosphonate, 97 %
1-Dimethoxyphosphorylpropan-2-one
Dimethyl Acetyl Methyl Phosphonate
Dimethyl 2-oxopropylphosphonate | [EINECS(EC#)]
224-110-5 | [Molecular Formula]
C5H11O4P | [MDL Number]
MFCD00008769 | [Molecular Weight]
166.11 | [MOL File]
4202-14-6.mol |
| Chemical Properties | Back Directory | [Appearance]
CLEAR COLOURLESS TO LIGHT BROWN LIQUID | [Boiling point ]
76-79 °C3 mm Hg(lit.) | [density ]
1.202 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.439(lit.)
| [Fp ]
200 °F
| [storage temp. ]
2-8°C | [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 Data | Back Directory | [Hazard Codes ]
Xi | [Safety Statements ]
S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) .
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
3
| [F ]
10 | [Hazard Note ]
Irritant | [HS Code ]
29310095 | [Storage Class]
10 - Combustible liquids |
| Hazard Information | Back Directory | [Chemical Properties]
CLEAR COLOURLESS TO LIGHT BROWN LIQUID | [Uses]
Reagent used together with tosyl azide in a one-pot alkynylation of aldehydes. | [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]
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 |
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