2-chloroethyl chloromethyl ether
triethyl phosphite
2-chloroethoxymethyl phosphonic acid diethyl ester
Conditions | Yield |
---|---|
at 125 - 140℃; for 4h; Arbuzov Reaction; | 100% |
at 125℃; Arbuzov reaction; | 82% |
at 110℃; for 7h; | |
at 80℃; for 3h; Neat (no solvent); |
diethyl 2-hydroxyethoxymethanephosphonate
2-chloroethoxymethyl phosphonic acid diethyl ester
Conditions | Yield |
---|---|
With tetrachloromethane; triphenylphosphine for 4h; Heating; | 50% |
2-chloroethyl chloromethyl ether
triethyl phosphite
A
methylene chloride
B
2-chloroethoxymethyl phosphonic acid diethyl ester
Conditions | Yield |
---|---|
1) 90 min at 90 deg C 2) 4 h at 125 deg C; Yield given; |
2-((diethoxyphosphoryl)methoxy)ethyl acetate
2-chloroethoxymethyl phosphonic acid diethyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 99 percent / Dowex 50X8 (H(+)-form) / ethanol / 30 h / Heating 2: 50 percent / CCl4, triphenylphosphine / 4 h / Heating View Scheme |
2-chloroethoxymethyl phosphonic acid diethyl ester
4-chloro-2-oxabutanyl-1-phosphonic acid
Conditions | Yield |
---|---|
With trimethylsilyl bromide In acetonitrile at 20℃; Inert atmosphere; | 100% |
ethyl 6-methyl-4-phenyl-3,4-dihydropyrimidin-2(1H)-one-5-carboxylate
2-chloroethoxymethyl phosphonic acid diethyl ester
C21H31N2O7P
Conditions | Yield |
---|---|
Stage #1: ethyl 6-methyl-4-phenyl-3,4-dihydropyrimidin-2(1H)-one-5-carboxylate With potassium carbonate In acetonitrile at 20℃; Inert atmosphere; Stage #2: 2-chloroethoxymethyl phosphonic acid diethyl ester In acetonitrile at 20 - 85℃; Inert atmosphere; | 92% |
With potassium carbonate In acetonitrile at 20 - 85℃; |
2-chloroethoxymethyl phosphonic acid diethyl ester
nifetepimine
C21H30N3O9P
Conditions | Yield |
---|---|
Stage #1: nifetepimine With potassium carbonate In acetonitrile at 20℃; Inert atmosphere; Stage #2: 2-chloroethoxymethyl phosphonic acid diethyl ester In acetonitrile at 20 - 85℃; Inert atmosphere; | 92% |
With potassium carbonate In acetonitrile at 20 - 85℃; |
5-ethoxycarbonyl-4-phenyl-6-methyl-3,4-dihydropyrimidine-2(1H)-thione
2-chloroethoxymethyl phosphonic acid diethyl ester
Conditions | Yield |
---|---|
Stage #1: 5-ethoxycarbonyl-4-phenyl-6-methyl-3,4-dihydropyrimidine-2(1H)-thione With potassium carbonate In acetonitrile at 20℃; Inert atmosphere; Stage #2: 2-chloroethoxymethyl phosphonic acid diethyl ester In acetonitrile at 20 - 85℃; Inert atmosphere; | 90% |
ethyl 4-(4-hydroxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
2-chloroethoxymethyl phosphonic acid diethyl ester
ethyl 3-(2-((diethoxyphosphoryl)methoxy)ethyl)-4-(4-hydroxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
Conditions | Yield |
---|---|
Stage #1: ethyl 4-(4-hydroxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate With potassium carbonate In acetonitrile at 20℃; Inert atmosphere; Stage #2: 2-chloroethoxymethyl phosphonic acid diethyl ester In acetonitrile at 20 - 85℃; Inert atmosphere; | 85% |
With potassium carbonate In N,N-dimethyl-formamide; acetonitrile at 20 - 85℃; for 20h; |
2-chloroethoxymethyl phosphonic acid diethyl ester
Conditions | Yield |
---|---|
Stage #1: 5-ethoxycarbonyl-6-methyl-4-(4-hydroxyphenyl)-3,4-dihydropyrimidin-2(1H)-thione With potassium carbonate In acetonitrile at 20℃; Inert atmosphere; Stage #2: 2-chloroethoxymethyl phosphonic acid diethyl ester In acetonitrile at 20 - 85℃; Inert atmosphere; | 85% |
2-chloroethoxymethyl phosphonic acid diethyl ester
Conditions | Yield |
---|---|
Stage #1: 6-methyl-4-(4-nitro-phenyl)-2-thioxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid ethyl ester With potassium carbonate In acetonitrile at 20℃; Inert atmosphere; Stage #2: 2-chloroethoxymethyl phosphonic acid diethyl ester In acetonitrile at 20 - 85℃; Inert atmosphere; | 85% |
2-chloroethoxymethyl phosphonic acid diethyl ester
ethyl 6-methyl-4-(4-nitrophenyl)-2-oxo-1,2,3,4-tetrahydro-5-pyrimidinecarboxylate
C21H30N3O9P
Conditions | Yield |
---|---|
Stage #1: ethyl 6-methyl-4-(4-nitrophenyl)-2-oxo-1,2,3,4-tetrahydro-5-pyrimidinecarboxylate With potassium carbonate In acetonitrile at 20℃; Inert atmosphere; Stage #2: 2-chloroethoxymethyl phosphonic acid diethyl ester In acetonitrile at 20 - 85℃; Inert atmosphere; | 83% |
With potassium carbonate In acetonitrile at 20 - 85℃; |
2-chloroethoxymethyl phosphonic acid diethyl ester
ethyl 6-methyl-4-(3-nitrophenyl)-2-thioxo-1,2,3,4-tetrahydropyrimidin-5-carboxylate
Conditions | Yield |
---|---|
Stage #1: ethyl 6-methyl-4-(3-nitrophenyl)-2-thioxo-1,2,3,4-tetrahydropyrimidin-5-carboxylate With potassium carbonate In acetonitrile at 20℃; Inert atmosphere; Stage #2: 2-chloroethoxymethyl phosphonic acid diethyl ester In acetonitrile at 20 - 85℃; Inert atmosphere; | 83% |
2-chloroethoxymethyl phosphonic acid diethyl ester
Conditions | Yield |
---|---|
With sodium iodide In acetone for 24h; Finkelstein Reaction; Reflux; Green chemistry; | 83% |
With potassium iodide In tetrahydrofuran at 45℃; for 1h; |
2-chloroethoxymethyl phosphonic acid diethyl ester
ethyl 4-(4-fluorophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
Conditions | Yield |
---|---|
Stage #1: ethyl 4-(4-fluorophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate With potassium carbonate In acetonitrile at 20℃; Inert atmosphere; Stage #2: 2-chloroethoxymethyl phosphonic acid diethyl ester In acetonitrile at 20 - 85℃; Inert atmosphere; | 82% |
ethyl 4-(2-hydroxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
2-chloroethoxymethyl phosphonic acid diethyl ester
C21H31N2O8P
Conditions | Yield |
---|---|
Stage #1: ethyl 4-(2-hydroxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate With potassium carbonate In acetonitrile at 20℃; Inert atmosphere; Stage #2: 2-chloroethoxymethyl phosphonic acid diethyl ester In acetonitrile at 20 - 85℃; Inert atmosphere; | 80% |
With potassium carbonate In acetonitrile at 20 - 85℃; |
2-chloroethoxymethyl phosphonic acid diethyl ester
ethyl 1,2,3,4-tetrahydro-4-(2-hydroxyphenyl)-6-methyl-2-thioxopyrimidine-5-carboxylate
Conditions | Yield |
---|---|
Stage #1: ethyl 1,2,3,4-tetrahydro-4-(2-hydroxyphenyl)-6-methyl-2-thioxopyrimidine-5-carboxylate With potassium carbonate In acetonitrile at 20℃; Inert atmosphere; Stage #2: 2-chloroethoxymethyl phosphonic acid diethyl ester In acetonitrile at 20 - 85℃; Inert atmosphere; | 80% |
2-chloroethoxymethyl phosphonic acid diethyl ester
5-methoxycarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid
Conditions | Yield |
---|---|
Stage #1: 5-methoxycarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid With potassium carbonate In acetonitrile at 20℃; Inert atmosphere; Stage #2: 2-chloroethoxymethyl phosphonic acid diethyl ester In acetonitrile at 20 - 85℃; Inert atmosphere; | 78% |
2-chloroethoxymethyl phosphonic acid diethyl ester
4-(4-fluoro-phenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid ethyl ester
Conditions | Yield |
---|---|
Stage #1: 4-(4-fluoro-phenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid ethyl ester With potassium carbonate In acetonitrile at 20℃; Inert atmosphere; Stage #2: 2-chloroethoxymethyl phosphonic acid diethyl ester In acetonitrile at 20 - 85℃; Inert atmosphere; | 77% |
2-chloroethoxymethyl phosphonic acid diethyl ester
diethyl <(2-azidoethoxy)methyl>phosphonate
Conditions | Yield |
---|---|
With sodium azide; tetrabutylammomium bromide In toluene at 90℃; for 4h; | 73% |
With sodium azide; tetrabutylammomium bromide In toluene at 90℃; for 4h; | 68% |
2-chloroethoxymethyl phosphonic acid diethyl ester
potassium phtalimide
[2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-ethoxymethyl]-phosphonic acid diethyl ester
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 120℃; for 7h; | 73% |
2-chloroethoxymethyl phosphonic acid diethyl ester
6-methylthiopurine
[2-(6-Methylsulfanyl-purin-9-yl)-ethoxymethyl]-phosphonic acid diethyl ester
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide 1)At 50 deg C for 1 h 2) addition of IIb,50 deg C for 22 h; | 71% |
2-chloroethoxymethyl phosphonic acid diethyl ester
2-Amino-6-chloropurin
A
2-amino-6-chloro-9-[2-(phosphonomethoxy)ethyl]purine bisethyl ester
B
7-(2-Diethoxyphosphonylmethoxyethyl)-2-amino-6-chloropurine
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 16h; | A 64% B 12% |
2-benzyl-2H-1,2,4-benzothiadiazin-3(4H)-one 1,1-dioxide
2-chloroethoxymethyl phosphonic acid diethyl ester
Conditions | Yield |
---|---|
With sodium hydride; potassium iodide In N,N-dimethyl-formamide at 80℃; Cooling with ice; | 60% |
2-chloroethoxymethyl phosphonic acid diethyl ester
2,6-diaminopurine
[2-(2,6-Diamino-purin-9-yl)-ethoxymethyl]-phosphonic acid diethyl ester
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide 1) 80 deg C for 1 h 2) After addition IIb 80 deg C for 24 h; | 58% |
2-chloroethoxymethyl phosphonic acid diethyl ester
4H-benzo[e][1,2,4]thiadiazine-1,1-dioxide
Conditions | Yield |
---|---|
Stage #1: 4H-benzo[e][1,2,4]thiadiazine-1,1-dioxide With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.5h; Cooling with ice; Stage #2: 2-chloroethoxymethyl phosphonic acid diethyl ester With potassium iodide In N,N-dimethyl-formamide; mineral oil at 50℃; | 49% |
2-chloroethoxymethyl phosphonic acid diethyl ester
[[2-(6-amino-9H-purine-9-yl)ethoxy]methyl]phosphonic acid diethyl ester
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 80℃; for 15h; | 46% |
Stage #1: adenine With potassium carbonate In N,N-dimethyl-formamide at 25 - 85℃; for 1h; Stage #2: 2-chloroethoxymethyl phosphonic acid diethyl ester In N,N-dimethyl-formamide for 20h; | |
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 80℃; for 5h; |
4-methoxy-5-methyl-pyrimidin-2(1H)-one
2-chloroethoxymethyl phosphonic acid diethyl ester
[2-(4-Methoxy-5-methyl-2-oxo-2H-pyrimidin-1-yl)-ethoxymethyl]-phosphonic acid diethyl ester
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide 1) 80 deg C for 1 h b) addition of IIb,100 deg C for 15 h; | 45% |
2-chloroethoxymethyl phosphonic acid diethyl ester
O,O-diethyl (2-aminoethoxy)methylphosphonate
Conditions | Yield |
---|---|
Stage #1: 2-chloroethoxymethyl phosphonic acid diethyl ester With sodium azide; tetramethylammonium bromide In toluene at 70℃; Stage #2: With triphenylphosphine In toluene at 20℃; | |
Multi-step reaction with 2 steps 1: 73 percent / dimethylformamide / 7 h / 120 °C 2: hydrazine / ethanol / 1 h / Heating View Scheme | |
Multi-step reaction with 2 steps 1: 68 percent / tetrabutylammonium bromide, sodium azide / toluene / 4 h / 90 °C 2: 75 percent / triphenylphosphine / toluene / 1 h / Ambient temperature View Scheme |
2-chloroethoxymethyl phosphonic acid diethyl ester
6-ethyl>amino>-2(1H)-amino-5-nitropyrimidin-4(3H)-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: NaN3; N(CH3)4Br / toluene / 70 °C 1.2: Ph3P / toluene / 20 °C 2.1: 65 percent / acetone; methanol / 24 h / 20 °C View Scheme | |
Multi-step reaction with 3 steps 1: 68 percent / tetrabutylammonium bromide, sodium azide / toluene / 4 h / 90 °C 2: 75 percent / triphenylphosphine / toluene / 1 h / Ambient temperature 3: 50.2 percent / acetone / 12 h / Ambient temperature View Scheme |
Diethyl [(2-chloroethoxy)methyl]phosphonate , with the CAS register number 116384-56-6, has its systematic name which is diethyl [(2-chloroethoxy)methyl]phosphonate . And it also has other names, such as phosphonic acid,P-[(2-chloroethoxy)methyl]-,diethyl ester .
Characteristics of Diethyl [(2-chloroethoxy)methyl]phosphonate are as followings: (1)ACD/LogP: 0.90 ; (2)ACD/LogD (pH 5.5): 1 ; (3)ACD/LogD (pH 7.4): 1 ; (4)ACD/BCF (pH 5.5): 3 ; (5)ACD/BCF (pH 7.4): 3 ; (6)ACD/KOC (pH 5.5): 73 ; (7)ACD/KOC (pH 7.4): 73 ; (8)#H bond acceptors: 4 ; (9)#Freely Rotating Bonds: 8 ; (10)Polar Surface Area: 54.57 ; (11)Index of Refraction: 1.431 ; (12)Molar Refractivity: 51.438 cm3 ; (13)Molar Volume: 198.702 cm3 ; (14)Polarizability: 20.391 ×10-24cm3 ; (15)Surface Tension: 34.11 dyne/cm ; (16)Density: 1.161 g/cm3 ; (17)Flash Point: 164.17 °C ; (18)Enthalpy of Vaporization: 51.052 kJ/mol ; (19)Boiling Point: 292.335 °C at 760 mmHg ; (20)Vapour Pressure: 0.003 mmHg at 25°C.
Diethyl [(2-chloroethoxy)methyl]phosphonate is usually used in the medicine intermediate. And it is a very important intermediate in compounding the adefovir dipivoxil which is the new style of drug resisting hepatitis B virus, so it is very necessary in resisting virus.
Diethyl [(2-chloroethoxy)methyl]phosphonate could be used in the lab to be as the reactant to produce other substance. Diethyl [(2-chloroethoxy)methyl]phosphonate reacts with 4-methoxy-5-methyl-1H-pyrimidin-2-one in the reagent of Sodium hydride and the solvent of dimethylformamide, and the condition is as below: the temperature is 80 deg C; the reaction time is one hour. Through this way, you could get [2-(4-methoxy-5-methyl-2-oxo-2H-pyrimidin-1-yl)-ethoxymethyl]-phosphonic acid diethyl ester .
And you also could obtain Diethyl [(2-chloroethoxy)methyl]phosphonate in the lab. Prepare the reactant of Diethyl 2-Hydroxyethoxymethanephosphonate , and then let it react in the chemical reagent of CCl4, triphenylphosphine . Under the heating condition, and react for about 4 hours, finally you could get the Diethyl [(2-chloroethoxy)methyl]phosphonate . The productivity is 50%.
If you need, you could convert the following data information into the molecular structure:
SMILES: O=P(OCC)(OCC)COCCCl
InChI: InChI=1/C7H16ClO4P/c1-3-11-13(9,12-4-2)7-10-6-5-8/h3-7H2,1-2H3
InChIKey: SRYMPIRBPPQDPD-UHFFFAOYAE
Std. InChI: InChI=1S/C7H16ClO4P/c1-3-11-13(9,12-4-2)7-10-6-5-8/h3-7H2,1-2H3
Diethyl [(2-chloroethoxy)methyl]phosphonate has many suppliers in China, such as Ningbo Hi-Tech Biochemicals Co., Ltd, Chico Pharmaceutical Co., Ltd, and Fuxin Huifeng Chemical Co., Ltd, etc.
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