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4202-14-6

Basic Information
CAS No.: 4202-14-6
Name: Dimethyl acetylmethylphosphonate
Article Data: 34
Molecular Structure:
Molecular Structure of 4202-14-6 (Dimethyl acetylmethylphosphonate)
Formula: C5H11O4P
Molecular Weight: 166.114
Synonyms: Phosphonicacid, (2-oxopropyl)-, dimethyl ester (9CI);Phosphonic acid, acetonyl-,dimethyl ester (6CI,7CI,8CI);(2-Oxopropyl)phosphonic acid dimethyl ester;(Dimethylphosphono)acetone;Dimethyl (2-oxopropyl)phosphonate;Dimethylacetonylphosphonate;Dimethyl b-keto-propylphosphonate;
EINECS: 224-110-5
Density: 1.145 g/cm3
Melting Point: 76-79 °C at 3 mm Hg
Boiling Point: 227 °C at 760 mmHg
Flash Point: 105.3 °C
Appearance: Clear, colorless liquid.
Hazard Symbols:
Safety: 23-24/25
PSA: 62.41000
LogP: 1.06130
Synthetic route
78-95-5

chloroacetone

121-45-9

phosphorous acid trimethyl ester

4202-14-6

dimethyl (2-oxopropyl)phosphonate

Conditions
ConditionsYield
In toluene at 135℃; under 3750.38 - 15001.5 Torr; for 0.333333h; Arbuzov Reaction; Large scale;88%
Stage #1: chloroacetone With potassium iodide In acetone; acetonitrile at 20℃; for 2h;
Stage #2: phosphorous acid trimethyl ester In acetone; acetonitrile at 50℃; for 24h;
82%
Stage #1: chloroacetone With potassium iodide In acetone; acetonitrile at 20℃; for 2h; Irradiation;
Stage #2: phosphorous acid trimethyl ester In acetone; acetonitrile at 50℃; for 24h;
77%
103517-85-7, 103538-61-0

[2-(Methoxycarbonyl-hydrazono)-propyl]-phosphonic acid dimethyl ester

4202-14-6

dimethyl (2-oxopropyl)phosphonate

Conditions
ConditionsYield
With hydrogenchloride; acetone for 3h; Ambient temperature;82%
3019-04-3

iodoacetone

121-45-9

phosphorous acid trimethyl ester

4202-14-6

dimethyl (2-oxopropyl)phosphonate

Conditions
ConditionsYield
In toluene for 2h; Heating;74%
In benzene
In acetone; acetonitrile at 20℃; for 12h; Michaelis-Arbuzov reaction;101.3 g
In acetone; acetonitrile at 20 - 50℃; Inert atmosphere;41 g
868-85-9

Dimethyl phosphite

123-54-6

acetylacetone

4202-14-6

dimethyl (2-oxopropyl)phosphonate

Conditions
ConditionsYield
With dipotassium peroxodisulfate; silver(I) acetate In water; N,N-dimethyl-formamide at 85℃; for 24h; Inert atmosphere; Schlenk technique; chemoselective reaction;72%
78-95-5

chloroacetone

4202-14-6

dimethyl (2-oxopropyl)phosphonate

Conditions
ConditionsYield
With potassium iodide; phosphorous acid trimethyl ester In acetone; acetonitrile71%
868-85-9

Dimethyl phosphite

67-64-1

acetone

4202-14-6

dimethyl (2-oxopropyl)phosphonate

Conditions
ConditionsYield
With dipotassium peroxodisulfate; silver(I) acetate In water at 85℃; Inert atmosphere; Schlenk technique; chemoselective reaction;60%
79-20-9

acetic acid methyl ester

756-79-6

dimethyl methane phosphonate

4202-14-6

dimethyl (2-oxopropyl)phosphonate

Conditions
ConditionsYield
Stage #1: dimethyl methane phosphonate With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h;
Stage #2: acetic acid methyl ester In tetrahydrofuran; hexane at -78 - 0℃; Further stages.;
56%
Stage #1: dimethyl methane phosphonate With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h;
Stage #2: acetic acid methyl ester In tetrahydrofuran; hexane at -78 - 0℃;
55%
Stage #1: dimethyl methane phosphonate With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 3h;
Stage #2: acetic acid methyl ester In tetrahydrofuran; hexane at -78 - 0℃;
With lithium diisopropyl amide In tetrahydrofuran at -5 - 0℃; Inert atmosphere;
141-78-6

ethyl acetate

756-79-6

dimethyl methane phosphonate

4202-14-6

dimethyl (2-oxopropyl)phosphonate

Conditions
ConditionsYield
Stage #1: dimethyl methane phosphonate With n-butyllithium In hexane; toluene at -80℃; for 0.166667h; Inert atmosphere;
Stage #2: ethyl acetate In hexane; toluene at -80℃; for 1h; Inert atmosphere;
50%
With n-butyllithium 1.) THF, -78 deg C, 15 min, 2.) THF, -78 deg C, 30 min; Multistep reaction;
876-27-7

4-chlorophenyl acetate

54731-75-8

dimethyl (2-hydroxypropyl)phosphonate

A

4202-14-6

dimethyl (2-oxopropyl)phosphonate

B

(R)-dimethyl 2-acetyloxypropylphosphonate

Conditions
ConditionsYield
With (hydroxy)tetraphenylcyclopentadienyl-based ruthenium; Candida antarctica lipase B (Novozym-435) In toluene at 70℃; for 24h;A 16%
B 62 % Spectr.
78-95-5

chloroacetone

121-45-9

phosphorous acid trimethyl ester

A

4185-82-4

phosphoric acid isopropenyl ester dimethyl ester

B

4202-14-6

dimethyl (2-oxopropyl)phosphonate

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    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.) Fp 200 °F storage temp. 2-8°C solubility Difficult

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Chemistry

Molecule structure of Phosphonic acid,P-(2-oxopropyl)-, dimethyl ester (CAS NO.4202-14-6):

IUPAC Name: 1-Dimethoxyphosphorylpropan-2-one
Molecular Weight: 166.112201 [g/mol]
Molecular Formula: C5H11O4P
Index of Refraction: 1.405
Molar Refractivity: 35.6 cm3
Molar Volume: 145 cm3
Surface Tension: 32.9 dyne/cm
Density: 1.145 g/cm3
Flash Point: 105.3 °C
Enthalpy of Vaporization: 46.36 kJ/mol 
Melting Point: 76-79 °C at 3 mm Hg(lit.)
Boiling Point: 227 °C at 760 mmHg
Vapour Pressure: 0.0793 mmHg at 25 °C 
XLogP3: 0.9
H-Bond Acceptor: 4
Rotatable Bond Count: 4
Tautomer Count: 3
Exact Mass: 166.039495
MonoIsotopic Mass: 166.039495
Topological Polar Surface Area: 52.6
Heavy Atom Count: 10 
Canonical SMILES: CC(=O)CP(=O)(OC)OC
InChI: InChI=1S/C5H11O4P/c1-5(6)4-10(7,8-2)9-3/h4H2,1-3H3
InChIKey: UOWIYNWMROWVDG-UHFFFAOYSA-N
EINECS: 224-110-5
Product Categories of Phosphonic acid,P-(2-oxopropyl)-, dimethyl ester (CAS NO.4202-14-6): Horner-Emmons Reaction; Synthetic Organic Chemistry; Wittig & Horner-Emmons Reaction

Safety Profile

Hazard Codes: IrritantXi
Safety Statements: 23-24/25
S23:Do not breathe vapour. 
S24/25:Avoid contact with skin and eyes.
WGK Germany: 3
F: 10
Hazard Note: Irritant

Specification

 Phosphonic acid,P-(2-oxopropyl)-, dimethyl ester (CAS NO.4202-14-6) is also called Dimethyl (2-oxopropyl)phosphonate ; Dimethyl acetylmethylphosphonate ; Dimethyl acetonylphosphonate ; Dimethyl 2-oxopropylphosphonate .