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Diethyl [(2-chloroethoxy)methyl]phosphonate

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Name

Diethyl [(2-chloroethoxy)methyl]phosphonate

EINECS 1592732-453-0
CAS No. 116384-56-6 Density 1.161 g/cm3
PSA 54.57000 LogP 2.46540
Solubility N/A Melting Point N/A
Formula C7H16ClO4P Boiling Point 292.335 °C at 760 mmHg
Molecular Weight 230.628 Flash Point 164.17 °C
Transport Information N/A Appearance N/A
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 116384-56-6 (Diethyl [(2-chloroethoxy)methyl]phosphonate) Hazard Symbols N/A
Synonyms

Phosphonicacid, [(2-chloroethoxy)methyl]-, diethyl ester (9CI);

Article Data 7

Diethyl [(2-chloroethoxy)methyl]phosphonate Synthetic route

1462-33-5

2-chloroethyl chloromethyl ether

122-52-1

triethyl phosphite

116384-56-6

2-chloroethoxymethyl phosphonic acid diethyl ester

Conditions
ConditionsYield
at 125 - 140℃; for 4h; Arbuzov Reaction;100%
at 125℃; Arbuzov reaction;82%
at 110℃; for 7h;
at 80℃; for 3h; Neat (no solvent);
116384-55-5

diethyl 2-hydroxyethoxymethanephosphonate

116384-56-6

2-chloroethoxymethyl phosphonic acid diethyl ester

Conditions
ConditionsYield
With tetrachloromethane; triphenylphosphine for 4h; Heating;50%
1462-33-5

2-chloroethyl chloromethyl ether

122-52-1

triethyl phosphite

A

74-87-3

methylene chloride

B

116384-56-6

2-chloroethoxymethyl phosphonic acid diethyl ester

Conditions
ConditionsYield
1) 90 min at 90 deg C 2) 4 h at 125 deg C; Yield given;
100708-15-4

2-((diethoxyphosphoryl)methoxy)ethyl acetate

116384-56-6

2-chloroethoxymethyl phosphonic acid diethyl ester

Conditions
ConditionsYield
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
116384-56-6

2-chloroethoxymethyl phosphonic acid diethyl ester

1391871-33-2

4-chloro-2-oxabutanyl-1-phosphonic acid

Conditions
ConditionsYield
With trimethylsilyl bromide In acetonitrile at 20℃; Inert atmosphere;100%
123237-03-6, 5395-36-8

ethyl 6-methyl-4-phenyl-3,4-dihydropyrimidin-2(1H)-one-5-carboxylate

116384-56-6

2-chloroethoxymethyl phosphonic acid diethyl ester

1442461-39-3

C21H31N2O7P

Conditions
ConditionsYield
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℃;
116384-56-6

2-chloroethoxymethyl phosphonic acid diethyl ester

123371-44-8

nifetepimine

1442461-32-6

C21H30N3O9P

Conditions
ConditionsYield
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℃;
123043-88-9, 33458-26-3

5-ethoxycarbonyl-4-phenyl-6-methyl-3,4-dihydropyrimidine-2(1H)-thione

116384-56-6

2-chloroethoxymethyl phosphonic acid diethyl ester

C21H31N2O6PS

Conditions
ConditionsYield
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%
123629-41-4

ethyl 4-(4-hydroxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

116384-56-6

2-chloroethoxymethyl phosphonic acid diethyl ester

1442461-41-7

ethyl 3-(2-((diethoxyphosphoryl)methoxy)ethyl)-4-(4-hydroxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

Conditions
ConditionsYield
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;
116384-56-6

2-chloroethoxymethyl phosphonic acid diethyl ester

5-ethoxycarbonyl-6-methyl-4-(4-hydroxyphenyl)-3,4-dihydropyrimidin-2(1H)-thione

C21H31N2O7PS

Conditions
ConditionsYield
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%

Diethyl [(2-chloroethoxy)methyl]phosphonate Specification

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 cm ; (13)Molar Volume:  198.702 cm ; (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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