Conditions | Yield |
---|---|
With potassium hydroxide In ethanol; water at 20℃; | 100% |
With water; sodium hydroxide In ethanol at 20℃; Inert atmosphere; | 97% |
With hydrogenchloride; potassium hydroxide 1.) aq. EtOH, 20 h; | 95% |
Conditions | Yield |
---|---|
With 1% Pd/C; hydrogen In ethyl acetate | 99% |
With hydrogen; palladium on activated charcoal | |
With hydrogen; palladium on activated charcoal In ethanol |
Conditions | Yield |
---|---|
In toluene Michaelis-Arbuzov Synthesis; Reflux; | 68% |
C12H27O5PSi
diethylphosphonoacetic acid
Conditions | Yield |
---|---|
With hydrogen fluoride In acetonitrile | 62% |
Conditions | Yield |
---|---|
With phosphate buffer; immobilized enzyme preparation from Rhodococcus sp for 168h; Ambient temperature; pH 7.0; | 41% |
tert-butyl diethylphosphonoacetate
diethylphosphonoacetic acid
Conditions | Yield |
---|---|
With hydrogenchloride |
diethoxyphosphoryl-acetic acid ethyl ester
A
diethylphosphonoacetic acid
B
phosphonoacetic acid
C
phosphonoacetic acid ethyl ester
Conditions | Yield |
---|---|
With potassium hydroxide In water Product distribution; various reagents; |
Conditions | Yield |
---|---|
With n-butyllithium 1.) ether, THF, -65 deg C, 30 min, 2.) ether, -65 deg C, 5 min; -65 deg C to room temp., 2 h; Yield given. Multistep reaction; | |
With n-butyllithium 1.) THF, hexane, -78 deg C to -20 deg C, 30 min, 2.) THF, -78 deg C to -10 deg C, 2 h; Multistep reaction; | |
With n-butyllithium at -78℃; |
carbon dioxide
diethyl-1-magnesium chloride methanephosphonate
diethylphosphonoacetic acid
Conditions | Yield |
---|---|
With water 1.) ether, -70 deg. C.; 2.) ether, room. temp.; Yield given. Multistep reaction; |
Methyl diethylphosphonoacetate
A
diethylphosphonoacetic acid
B
diethylphosphinylacethydroxamic acid
Conditions | Yield |
---|---|
With sodium hydroxide; hydroxylamine hydrochloride In water at 20℃; for 18h; pH=12; Title compound not separated from byproducts; |
Conditions | Yield |
---|---|
With sodium hydroxide; hydroxylamine hydrochloride In water at 20℃; for 72h; pH=12; Title compound not separated from byproducts; |
diethyl iodomethanephosphonate
diethylphosphonoacetic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: isopropylmagnesium chloride / tetrahydrofuran / 0.75 h / -70 °C 2: 2.) H2O / 1.) ether, -70 deg. C.; 2.) ether, room. temp. View Scheme |
Diethyl phosphonate
bromoacetic acid
diethylphosphonoacetic acid
Conditions | Yield |
---|---|
With sodium ethanolate In ethanol; water |
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol; water |
diethylphosphonoacetic acid
(-)-menthol
(diethoxy-phosphoryl)-acetic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester
Conditions | Yield |
---|---|
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In ethyl acetate; toluene at 20℃; Inert atmosphere; | 100% |
With triethylamine; 2-chloropyridinium iodide |
diethylphosphonoacetic acid
diethyl (2-chloro-2-oxoethyl)phosphonate
Conditions | Yield |
---|---|
With oxalyl dichloride; N,N-dimethyl-formamide In benzene for 1h; | 100% |
With thionyl chloride at 20℃; for 2h; Inert atmosphere; | 92% |
With thionyl chloride at 20℃; for 2h; Inert atmosphere; | 92% |
diethylphosphonoacetic acid
tert-butyl alcohol
tert-butyl diethylphosphonoacetate
Conditions | Yield |
---|---|
With dicyclohexyl-carbodiimide In dichloromethane at 25℃; for 0.25h; | 100% |
With dicyclohexyl-carbodiimide In dichloromethane at 25℃; for 0.25h; Product distribution; Further Variations:; Reaction partners; Reagents; Solvents; | 100% |
With sulfuric acid In various solvent(s) for 12h; | 90% |
With dicyclohexyl-carbodiimide In acetonitrile at 25℃; for 1h; |
diethylphosphonoacetic acid
allyl alcohol
allyl diethylphosphonoacetate
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 18h; Esterification; | 100% |
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In tetrahydrofuran; ethyl acetate; toluene at 20℃; Inert atmosphere; |
Conditions | Yield |
---|---|
With dmap; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate In dichloromethane at 20℃; for 48h; | 100% |
With dmap; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate In dichloromethane | 99% |
diethylphosphonoacetic acid
4-(Dimethylamino)butylamine
[(4-dimethylamino-butylcarbamoyl)-methyl]-phosphonic acid diethyl ester
Conditions | Yield |
---|---|
With N'-methyl polystyrene; N-cyclohexylcarbodimide; benzotriazol-1-ol; tris(2-amimoethyl)amine polystyrene In dichloromethane; N,N-dimethyl acetamide at 20℃; for 24h; | 100% |
diethylphosphonoacetic acid
Conditions | Yield |
---|---|
With dmap; PS-carbodiimide; 4-(dimethylamino)pyridine hydrochloride In chloroform for 0.5h; | 100% |
diethylphosphonoacetic acid
4-bromo-phenol
(para-bromophenyl)diethylphosphonoacetate
Conditions | Yield |
---|---|
With dicyclohexyl-carbodiimide; dmap In dichloromethane at 0 - 20℃; for 10h; Addition; | 100% |
Conditions | Yield |
---|---|
With N,N,N,N,-tetramethylethylenediamine; zinc trifluoromethanesulfonate; 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 25℃; for 12h; Horner-Wadsworth-Emmons reaction; | 100% |
diethylphosphonoacetic acid
cyclohexanol
cyclohexyl 2-(diethoxyphosphoryl)acetate
Conditions | Yield |
---|---|
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In tetrahydrofuran; ethyl acetate; toluene at 20℃; for 4h; Inert atmosphere; | 100% |
With dicyclohexyl-carbodiimide In dichloromethane for 0.25h; |
diethylphosphonoacetic acid
diethyl[2-({(3E)-1-[(6-fluoro-2-naphthyl)methyl]-pyrrolidin-3-yl}amino)-2-oxoethyl]phosphonate
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃; for 3.5h; | 100% |
diethylphosphonoacetic acid
cyclopropanemethylamine
diethyl {[(cyclopropylmethyl)carbamoyl]methyl}phosphonate
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; water for 12h; | 100% |
diethylphosphonoacetic acid
(2-(2-(2-(4-(1-aminobutyl)phenoxy)ethoxy)ethoxy)ethyl)imidodicarbonic acid bis(tert-butyl) ester
(2-(2-(2-(4-(1-(2-(diethoxyphosphoryl)acetamido)butyl)phenoxy)ethoxy)ethoxy)ethyl)imidodicarbonic acid bis(tert-butyl) ester
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 3h; Inert atmosphere; | 100% |
diethylphosphonoacetic acid
(2R,3S,6S)-7-(benzyloxy)-1-((tert-butyldimethylsilyl)oxy)-2,6-dimethyl-5-methyleneheptan-3-ol
(2R,3S,6S)-7-(benzyloxy)-1-((tert-butyldimethylsilyl)oxy)-2,6-dimethyl-5-methyleneheptan-3-yl 2-(diethoxyphosphoryl)acetate
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 0.5h; | 100% |
diethylphosphonoacetic acid
(2S,3S,6S)-7-(benzyloxy)-1-((tert-butyldimethylsilyl)oxy)-2,6-dimethyl-5-methyleneheptan-3-ol
(2S,3S,6S)-7-(benzyloxy)-1-((tert-butyldimethylsilyl)oxy)-2,6-dimethyl-5-methyleneheptan-3-yl 2-(diethoxyphosphoryl)acetate
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 0.5h; | 100% |
diethylphosphonoacetic acid
2-phenylethanol
phenethyl 2-(diethoxyphosphoryl)acetate
Conditions | Yield |
---|---|
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In ethyl acetate; toluene at 20℃; for 4h; Inert atmosphere; | 100% |
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In tetrahydrofuran; ethyl acetate; toluene at 20℃; for 4h; Inert atmosphere; |
diethylphosphonoacetic acid
2-(4-Methoxyphenyl)ethanol
4-methoxyphenethyl 2-(diethoxyphosphoryl)acetate
Conditions | Yield |
---|---|
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In ethyl acetate; toluene at 20℃; for 4h; Inert atmosphere; | 100% |
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In tetrahydrofuran; ethyl acetate; toluene at 20℃; for 4h; Inert atmosphere; |
diethylphosphonoacetic acid
3,4-methylenedioxyphenethyl alcohol
2-(1,3-benzodioxol-5-yl)ethyl 2-(diethoxyphosphoryl)acetate
Conditions | Yield |
---|---|
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In ethyl acetate; toluene at 20℃; for 4h; Inert atmosphere; | 100% |
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In tetrahydrofuran; ethyl acetate; toluene at 20℃; for 4h; Inert atmosphere; |
diethylphosphonoacetic acid
(RS)-2-phenyl-1-propanol
2-phenylpropyl 2-(diethoxyphosphoryl)acetate
Conditions | Yield |
---|---|
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In ethyl acetate; toluene at 20℃; for 4h; Inert atmosphere; | 100% |
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In tetrahydrofuran; ethyl acetate; toluene at 20℃; for 4h; Inert atmosphere; |
diethylphosphonoacetic acid
n-heptan1ol
heptyl 2-(diethoxyphosphoryl)acetate
Conditions | Yield |
---|---|
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In ethyl acetate; toluene at 20℃; for 4h; Inert atmosphere; | 100% |
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In tetrahydrofuran; ethyl acetate; toluene at 20℃; for 4h; Inert atmosphere; |
diethylphosphonoacetic acid
3-trimethylsilyl-1-propanol
3-(trimethylsilyl)propyl 2-(diethoxyphosphoryl)acetate
Conditions | Yield |
---|---|
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In ethyl acetate; toluene at 20℃; for 4h; Inert atmosphere; | 100% |
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In tetrahydrofuran; ethyl acetate; toluene at 20℃; for 4h; Inert atmosphere; |
diethylphosphonoacetic acid
1-amino-cyclopentanemethanol
cyclopentylmethyl 2-(diethoxyphosphoryl)acetate
Conditions | Yield |
---|---|
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In ethyl acetate; toluene at 20℃; for 4h; Inert atmosphere; | 100% |
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In tetrahydrofuran; ethyl acetate; toluene at 20℃; for 4h; Inert atmosphere; |
Conditions | Yield |
---|---|
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In tetrahydrofuran; ethyl acetate; toluene at 20℃; for 4h; Inert atmosphere; | 100% |
diethylphosphonoacetic acid
2-(4-dimethylaminophenyl)ethyl alcohol
Conditions | Yield |
---|---|
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In tetrahydrofuran; ethyl acetate; toluene at 20℃; for 4h; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In tetrahydrofuran; ethyl acetate; toluene at 20℃; for 4h; Inert atmosphere; | 100% |
diethylphosphonoacetic acid
2-methyl-propan-1-ol
diethyl <(iso-butoxycarbonyl)methyl>phosphonate
Conditions | Yield |
---|---|
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In tetrahydrofuran; ethyl acetate; toluene at 20℃; for 4h; Inert atmosphere; | 100% |
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In toluene at 20℃; for 4h; Inert atmosphere; | 95% |
diethylphosphonoacetic acid
Conditions | Yield |
---|---|
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In tetrahydrofuran; toluene at 20℃; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 71h; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In tetrahydrofuran; ethyl acetate; toluene at 20℃; Inert atmosphere; | 100% |
The Acetic acid,2-(diethoxyphosphinyl)-, with the CAS registry number 3095-95-2, is also known as Diethylphosphonoacetic acid. It belongs to the product categories of C-C Bond Formation; Horner-Wadsworth-Emmons Reagents; Olefination. This chemical's molecular formula is C6H13O5P and molecular weight is 196.138181. Its IUPAC name is called 2-diethoxyphosphorylacetic acid. The product should be sealed and stored in cool, dry place.
Physical properties of Acetic acid,2-(diethoxyphosphinyl)-: (1)ACD/LogP: -0.08; (2)ACD/LogD (pH 5.5): -2.09; (3)ACD/LogD (pH 7.4): -3.6; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 1; (7)ACD/KOC (pH 7.4): 1; (8)#H bond acceptors: 5; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 6; (11)Index of Refraction: 1.438; (12)Molar Refractivity: 41.77 cm3; (13)Molar Volume: 159 cm3; (14)Surface Tension: 41.6 dyne/cm; (15)Density: 1.233 g/cm3; (16)Flash Point: 144.9 °C; (17)Enthalpy of Vaporization: 61.27 kJ/mol; (18)Boiling Point: 315.9 °C at 760 mmHg; (19)Vapour Pressure: 9.07E-05 mmHg at 25°C.
Preparation: this chemical can be prepared by diethoxyphosphoryl-acetic acid ethyl ester. This reaction will need reagent potassium hydroxide and solvent ethanol, H2O. The reaction time is 15 hours with reaction temperature of 20 °C. The yield is about 69%.
Uses of Acetic acid,2-(diethoxyphosphinyl)-: it can be used to produce (1-pyrrolidin-1-ylmethyl-vinyl)-phosphonic acid diethyl ester by heating. This reaction will need solvent benzene with reaction time of 6 hours. The yield is about 80%.
When you are using this chemical, please be cautious about it as the following:
This chemical may cause damage to health. It is harmful if swallowed. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. Whenever you will contact it, please wear suitable protective gloves and eye/face protection.
You can still convert the following datas into molecular structure:
(1)Canonical SMILES: CCOP(=O)(CC(=O)O)OCC
(2)InChI: InChI=1S/C6H13O5P/c1-3-10-12(9,11-4-2)5-6(7)8/h3-5H2,1-2H3,(H,7,8)
(3)InChIKey: DVQMPWOLBFKUMM-UHFFFAOYSA-N
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