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Cas Database |
| Name |
Dimethyl acetylmethylphosphonate |
EINECS | 224-110-5 |
| CAS No. | 4202-14-6 | Density | 1.145 g/cm3 |
| PSA | 62.41000 | LogP | 1.06130 |
| Solubility | N/A | Melting Point |
76-79 °C at 3 mm Hg |
| Formula | C5H11O4P | Boiling Point | 227 °C at 760 mmHg |
| Molecular Weight | 166.114 | Flash Point | 105.3 °C |
| Transport Information | N/A | Appearance | Clear, colorless liquid. |
| Safety | 23-24/25 | Risk Codes | N/A |
| Molecular Structure |
|
Hazard Symbols |
|
| 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; |
Article Data | 34 |
Dimethyl acetylmethylphosphonate Synthetic route
- 78-95-5
chloroacetone
- 121-45-9
phosphorous acid trimethyl ester
- 4202-14-6
dimethyl (2-oxopropyl)phosphonate
| Conditions | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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 |
| Conditions | Yield |
|---|---|
| With dipotassium peroxodisulfate; silver(I) acetate In water; N,N-dimethyl-formamide at 85℃; for 24h; Inert atmosphere; Schlenk technique; chemoselective reaction; | 72% |
| Conditions | Yield |
|---|---|
| With potassium iodide; phosphorous acid trimethyl ester In acetone; acetonitrile | 71% |
| Conditions | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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; |
| Conditions | Yield |
|---|---|
| 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
| Conditions | Yield |
|---|---|
| With (hydroxy)tetraphenylcyclopentadienyl-based ruthenium; Candida antarctica lipase B (Novozym-435) In toluene at 70℃; for 24h; | A 16% B 62 % Spectr. |
Dimethyl acetylmethylphosphonate Chemical Properties
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
Dimethyl acetylmethylphosphonate Safety Profile
Hazard Codes: 
Xi
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
Dimethyl acetylmethylphosphonate 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 .
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