Dimethyl acetylmethylphosphonate Chemical Properties

Boiling point:

76-79 °C3 mm Hg(lit.)

Density 

1.202 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.439(lit.)

Flash point:

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

MSDS

• Language:English Provider:Dimethyl acetylmethylphosphonate
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Dimethyl acetylmethylphosphonate Usage And Synthesis

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

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(4202-14-6)Related Product Information

• Acetylacetone
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• Dimethyl sulfoxide
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• Dimethyl carbonate
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• N,N-Dimethylformamide
• Dimethyl sulfate
• ETHANE
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• Diethyl (2-oxopropyl)phosphonate
• Piperonyl acetone
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• DIMETHYL (2-OXOHEPTYL)PHOSPHONATE
• Dimethyl methylphosphonate