ChemicalBook--->CAS DataBase List--->4202-14-6

4202-14-6

4202-14-6 Structure

4202-14-6 Structure
IdentificationMore
[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 PropertiesBack 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 DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H227
[Precautionary statements ]

P210e-P280a-P370+P378a-P501a-P210-P280-P403+P235-P501
[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
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Acetone-->Acetonitrile-->Potassium iodide-->Trimethyl phosphite-->Chloroacetone-->Ethyl acetate-->Dimethyl methylphosphonate
Material Safety Data Sheet(MSDS)Back Directory
[msds information]

Dimethyl acetylmethylphosphonate(4202-14-6).msds
Hazard InformationBack 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]

Chloroacetone

78-95-5

Trimethyl phosphite

121-45-9

Dimethyl acetylmethylphosphonate

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
Spectrum DetailBack Directory
[Spectrum Detail]

Dimethyl acetylmethylphosphonate(4202-14-6)MS
Dimethyl acetylmethylphosphonate(4202-14-6)1HNMR
Dimethyl acetylmethylphosphonate(4202-14-6)13CNMR
Dimethyl acetylmethylphosphonate(4202-14-6)IR1
Dimethyl acetylmethylphosphonate(4202-14-6)Raman
Well-known Reagent Company Product InformationBack Directory
[Acros Organics]

Dimethyl (2-oxopropyl)phosphonate, 95%(4202-14-6)
[Alfa Aesar]

Dimethyl acetylmethylphosphonate, 97%(4202-14-6)
[Sigma Aldrich]

4202-14-6(sigmaaldrich)
[TCI AMERICA]

Dimethyl (2-Oxopropyl)phosphonate,>95.0%(GC)(4202-14-6)
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