Product Name

  • Name

    Adefovir

  • EINECS 600-789-7
  • CAS No. 106941-25-7
  • Article Data21
  • CAS DataBase
  • Density 1.88 g/cm3
  • Solubility
  • Melting Point >260 °C
  • Formula C8H12N5O4P
  • Boiling Point 632.5 °C at 760 mmHg
  • Molecular Weight 273.188
  • Flash Point 336.3 °C
  • Transport Information
  • Appearance white to off-white powder
  • Safety 45
  • Risk Codes 25
  • Molecular Structure Molecular Structure of 106941-25-7 (Adefovir)
  • Hazard Symbols T
  • Synonyms ((2-(6-Amino-9H-purin-9-yl)ethoxy)methyl)phosphonic acid;9-(2-Phosphorylmethoxyethyl)adenine;PMEA;Adefovir [USAN:INN];2-(6-aminopurin-9-yl)ethoxymethylphosphonic acid;N-(2-Phophonomethoxyethyl-2,6-diaminopurine);GS 0393;GS 393;9-(2-(Phosphonomethoxy)ethyl)adenine;Phosphonic acid, ((2-(6-amino-9H-purin-9-yl)ethoxy)methyl)-;9-[2-Phosphonylmethoxyethyl]adenine;9-[2-(Phosphonomethoxy)ethyl]adenine (PMEA);9-[2-phosphonyl methoxyethyl]adenine;Adefovir dipivox;9-[2-(phosphonomethoxy)ethyl]adenine;[[2-(6-amino-9H-purin-9-yl) ethoxy] methyl] phosphonic acid;9-(2-phosphonyl methoxyethyl)adenine;Adefovir Dipivozil;9-(2-Phosphonylmethoxyethyl)adenine;
  • PSA 146.19000
  • LogP 0.14150

Synthetic route

[[2-(6-amino-9H-purine-9-yl)ethoxy]methyl]phosphonic acid diethyl ester
116384-53-3

[[2-(6-amino-9H-purine-9-yl)ethoxy]methyl]phosphonic acid diethyl ester

Adefovir
106941-25-7

Adefovir

Conditions
ConditionsYield
With trimethylsilyl bromide95%
Stage #1: [[2-(6-amino-9H-purine-9-yl)ethoxy]methyl]phosphonic acid diethyl ester With trimethylsilyl bromide In acetonitrile at 20℃; for 3h; Large scale;
Stage #2: With sodium hydroxide In water for 2h; Reflux; Large scale;
86.3%
With hydrogen bromide In water at 90℃; for 5h; Temperature; Time;86%
[2-(6-Amino-purin-9-yl)-ethoxymethyl]-phosphonic acid diisopropyl ester
142340-94-1

[2-(6-Amino-purin-9-yl)-ethoxymethyl]-phosphonic acid diisopropyl ester

Adefovir
106941-25-7

Adefovir

Conditions
ConditionsYield
With hydrogenchloride In water at 140℃; for 0.166667h; Microwave irradiation; Sealed tube;95%
Multi-step reaction with 2 steps
1: acetonitrile
2: aq. NH3
View Scheme
Methyl Ester of 9-(2-Phosphonylmethoxyethyl)adenine
107021-27-2

Methyl Ester of 9-(2-Phosphonylmethoxyethyl)adenine

Adefovir
106941-25-7

Adefovir

Conditions
ConditionsYield
With trimethylsilyl iodide; triethylamine carbonate 1) DMF, R.T., 16 h 2) 80 deg C; Yield given. Multistep reaction;
diethyl (p-toluenesulfonyloxymethane)phosphonate
31618-90-3

diethyl (p-toluenesulfonyloxymethane)phosphonate

9-(2-hydroxyethyl)adenine
707-99-3

9-(2-hydroxyethyl)adenine

Adefovir
106941-25-7

Adefovir

Conditions
ConditionsYield
With trimethylsilyl bromide; sodium t-butanolate 1.) DMF; Yield given. Multistep reaction;
C14H28N5O4PSi2

C14H28N5O4PSi2

Adefovir
106941-25-7

Adefovir

Conditions
ConditionsYield
With ammonium hydroxide Yield given;
With water33.0 g
[2-(5-Amino-6-chloro-pyrimidin-4-ylamino)-ethoxymethyl]-phosphonic acid diethyl ester
212894-84-3

[2-(5-Amino-6-chloro-pyrimidin-4-ylamino)-ethoxymethyl]-phosphonic acid diethyl ester

Adefovir
106941-25-7

Adefovir

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 92 percent / 3 h / 120 °C
2: 87 percent / NH3 liquid / tetrahydrofuran; dimethylsulfoxide / 24 h / 25 °C
3: 95 percent / TMSBr
View Scheme
O,O-diethyl((2-(6-chloro-9H-purin-9-yl)ethoxy)methyl)phosphonate
185900-69-0

O,O-diethyl((2-(6-chloro-9H-purin-9-yl)ethoxy)methyl)phosphonate

Adefovir
106941-25-7

Adefovir

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 87 percent / NH3 liquid / tetrahydrofuran; dimethylsulfoxide / 24 h / 25 °C
2: 95 percent / TMSBr
View Scheme
9-(2-Hydroxyethyl)-N6-benzoyladenine
55343-28-7

9-(2-Hydroxyethyl)-N6-benzoyladenine

Adefovir
106941-25-7

Adefovir

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1) NaH 2) 0.5 mol l-1 NaOH / 1)DMF, R.T., 48 h, 2) 50 deg C, 6 h
2: 1) iodotrimethylsilane 2) 2 mol l-1 triethylammonium hydrogen carbonate / 1) DMF, R.T., 16 h 2) 80 deg C
View Scheme
9-(2-hydroxyethyl)adenine
707-99-3

9-(2-hydroxyethyl)adenine

Adefovir
106941-25-7

Adefovir

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 81 percent / chlorotrimethylsilane / pyridine
2: 1) NaH 2) 0.5 mol l-1 NaOH / 1)DMF, R.T., 48 h, 2) 50 deg C, 6 h
3: 1) iodotrimethylsilane 2) 2 mol l-1 triethylammonium hydrogen carbonate / 1) DMF, R.T., 16 h 2) 80 deg C
View Scheme
Multi-step reaction with 2 steps
1: 1) NaH, 2) 0.5 mol l-1 NaOH / 1) DMF, R.T., 48 h, 2) 50 deg C, 6 h
2: 1) iodotrimethylsilane 2) 2 mol l-1 triethylammonium hydrogen carbonate / 1) DMF, R.T., 16 h 2) 80 deg C
View Scheme
Multi-step reaction with 2 steps
1.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 5 °C / Large scale
1.2: 5 h / 5 °C / Large scale
2.1: trimethylsilyl bromide / acetonitrile / 3 h / 20 °C / Large scale
2.2: 2 h / Reflux; Large scale
View Scheme
Multi-step reaction with 2 steps
1: magnesium 2-methylpropan-2-olate / N,N-dimethyl-formamide / 12 h / 80 °C
2: chloro-trimethyl-silane / chlorobenzene / 10 h / 120 °C
View Scheme
Multi-step reaction with 2 steps
1.1: magnesium 2-methylpropan-2-olate / N,N-dimethyl-formamide / 1 h / 78 - 82 °C
1.2: 78 - 82 °C
2.1: trimethylsilyl bromide / 80 - 85 °C
View Scheme
9-(2-Diethoxyphosphonomethoxyethyl)adenine

9-(2-Diethoxyphosphonomethoxyethyl)adenine

trimethylsilyl bromide
2857-97-8

trimethylsilyl bromide

Adefovir
106941-25-7

Adefovir

Conditions
ConditionsYield
In dichloromethane; water; acetone
disodium {[2-(6-amino-9H-purin-9-yl)ethoxy]methyl}phosphonothioate

disodium {[2-(6-amino-9H-purin-9-yl)ethoxy]methyl}phosphonothioate

Adefovir
106941-25-7

Adefovir

Conditions
ConditionsYield
for 24h; Conversion of starting material; Complete medium (extra-cellular medium mimick);
With CEM-SS culture medium at 37℃; pH=7.4; aq. buffer;
{[2-(6-amino-9H-purin-9-yl)ethoxy]methyl}phosphinic acid
159531-21-2

{[2-(6-amino-9H-purin-9-yl)ethoxy]methyl}phosphinic acid

Adefovir
106941-25-7

Adefovir

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: pyridine; N,O-bis-(trimethylsilyl)-acetamide / 1 h / 20 °C / Inert atmosphere
1.2: 0.5 h / Inert atmosphere
1.3: Dowex 50WX2 (Na+ form)
2.1: CEM-SS culture medium / 37 °C / pH 7.4 / aq. buffer
View Scheme
Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 25 - 85 °C
1.2: 20 h
2.1: water; hydrogen bromide / 4 h / 90 - 95 °C
2.2: 25 - 30 °C / pH 2.8
View Scheme
Multi-step reaction with 3 steps
1: triethylamine / acetonitrile / 14 h / 125 °C / Inert atmosphere
2: magnesium 2-methylpropan-2-olate / N,N-dimethyl-formamide / 12 h / 80 °C
3: chloro-trimethyl-silane / chlorobenzene / 10 h / 120 °C
View Scheme
C32H41FN7O6P

C32H41FN7O6P

A

Adefovir
106941-25-7

Adefovir

B

PMEA-F

PMEA-F

Conditions
ConditionsYield
With ethylenediaminetetraacetic acid; DL-dithiothreitol; water; magnesium chloride In aq. buffer at 37℃; for 18h; pH=7.5; Enzymatic reaction;
adefovir dipivoxyl
142340-99-6

adefovir dipivoxyl

Adefovir
106941-25-7

Adefovir

Conditions
ConditionsYield
With ethylenediaminetetraacetic acid; DL-dithiothreitol; water; magnesium chloride In aq. buffer at 37℃; for 1h; pH=7.5; Enzymatic reaction;
C32H42N7O6P

C32H42N7O6P

Adefovir
106941-25-7

Adefovir

Conditions
ConditionsYield
With ethylenediaminetetraacetic acid; DL-dithiothreitol; water; magnesium chloride In aq. buffer at 37℃; for 18h; pH=7.5; Enzymatic reaction;
C18H30N7O6P
168537-58-4

C18H30N7O6P

Adefovir
106941-25-7

Adefovir

Conditions
ConditionsYield
With ethylenediaminetetraacetic acid; DL-dithiothreitol; water; magnesium chloride In aq. buffer at 37℃; for 18h; pH=7.5; Enzymatic reaction;
6-Chloro-9-(β-hydroxyethylamino)purine
1670-62-8

6-Chloro-9-(β-hydroxyethylamino)purine

Adefovir
106941-25-7

Adefovir

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium hydride / tetrahydrofuran / -20 - 0 °C / Inert atmosphere
1.2: 48 h / 50 °C
2.1: trimethylhalosilane / acetonitrile / 20 °C / Inert atmosphere; Cooling with ice
View Scheme
6-chloro-9-(ethoxycarbonylmethyl)-9H-purine
56791-59-4

6-chloro-9-(ethoxycarbonylmethyl)-9H-purine

Adefovir
106941-25-7

Adefovir

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: methanol; sodium tetrahydroborate / 0 °C
2.1: sodium hydride / tetrahydrofuran / -20 - 0 °C / Inert atmosphere
2.2: 48 h / 50 °C
3.1: trimethylhalosilane / acetonitrile / 20 °C / Inert atmosphere; Cooling with ice
View Scheme
6-chloropurine
87-42-3

6-chloropurine

Adefovir
106941-25-7

Adefovir

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: scandium tris(trifluoromethanesulfonate) / acetonitrile / 0.17 h / 20 °C
2.1: methanol; sodium tetrahydroborate / 0 °C
3.1: sodium hydride / tetrahydrofuran / -20 - 0 °C / Inert atmosphere
3.2: 48 h / 50 °C
4.1: trimethylhalosilane / acetonitrile / 20 °C / Inert atmosphere; Cooling with ice
View Scheme
(di-tert-butoxyphosphoryl)methyl methanesulfonate

(di-tert-butoxyphosphoryl)methyl methanesulfonate

9-(2-hydroxyethyl)adenine
707-99-3

9-(2-hydroxyethyl)adenine

Adefovir
106941-25-7

Adefovir

Conditions
ConditionsYield
Stage #1: 9-(2-hydroxyethyl)adenine With magnesium 2-methylpropan-2-olate In N,N-dimethyl acetamide at 90℃; for 0.5h; Schlenk technique; Inert atmosphere;
Stage #2: (di-tert-butoxyphosphoryl)methyl methanesulfonate In N,N-dimethyl acetamide at 90℃; for 22h; Schlenk technique; Inert atmosphere;
Stage #3: With hydrogenchloride In water at 60℃; Schlenk technique; Inert atmosphere;
morpholine
110-91-8

morpholine

N,N'-di-cyclohexylformamidine
2303-89-1

N,N'-di-cyclohexylformamidine

Adefovir
106941-25-7

Adefovir

9-(2-Morpholinophosphonylmethoxyethyl)adenine N,N'-dicyclohexylcarboxamidinium salt

9-(2-Morpholinophosphonylmethoxyethyl)adenine N,N'-dicyclohexylcarboxamidinium salt

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In water; tert-butyl alcohol for 11h; Heating;96%
Adefovir
106941-25-7

Adefovir

9-(2-Phosphonylmethoxyethyl)hypoxanthine
113884-65-4

9-(2-Phosphonylmethoxyethyl)hypoxanthine

Conditions
ConditionsYield
With isopentyl nitrite In acetic acid for 72h; Ambient temperature;93%
3,5-Dihydroxybenzoic acid
99-10-5

3,5-Dihydroxybenzoic acid

Adefovir
106941-25-7

Adefovir

C8H12N5O4P*C7H6O4*H2O

C8H12N5O4P*C7H6O4*H2O

Conditions
ConditionsYield
With water at 90℃; for 3h;90%
N-formyldiethylamine
617-84-5

N-formyldiethylamine

Adefovir
106941-25-7

Adefovir

C13H19Cl2N6O2P
1056998-35-6

C13H19Cl2N6O2P

Conditions
ConditionsYield
With oxalyl dichloride In dichloromethane for 4.5h; Heating / reflux;89%
With oxalyl dichloride In dichloromethane for 4.5h; Heating / reflux;
Adefovir
106941-25-7

Adefovir

(Z)-4-(2-chloroethylidenyl)-2,3-dimethoxy-Δα,β-butenolide
347363-99-9

(Z)-4-(2-chloroethylidenyl)-2,3-dimethoxy-Δα,β-butenolide

[2-(6-amino-purin-9-yl)-ethoxymethyl]-phosphonic acid mono-[2-(3,4-dimethoxy-5-oxo-5H-furan-2-ylidene)-ethyl] ester

[2-(6-amino-purin-9-yl)-ethoxymethyl]-phosphonic acid mono-[2-(3,4-dimethoxy-5-oxo-5H-furan-2-ylidene)-ethyl] ester

Conditions
ConditionsYield
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 25℃; for 1h;88%
1,1,1-trichloroethanol
115-20-8

1,1,1-trichloroethanol

Adefovir
106941-25-7

Adefovir

9-<2-(phosphonomethoxy)ethyl>adenine, mono-2,2,2-trichloroethyl ester

9-<2-(phosphonomethoxy)ethyl>adenine, mono-2,2,2-trichloroethyl ester

Conditions
ConditionsYield
With thionyl chloride In N,N-dimethyl-formamide for 16h; Ambient temperature;86%
methanol
67-56-1

methanol

Adefovir
106941-25-7

Adefovir

Methyl Ester of 9-(2-Phosphonylmethoxyethyl)adenine
107021-27-2

Methyl Ester of 9-(2-Phosphonylmethoxyethyl)adenine

Conditions
ConditionsYield
With thionyl chloride In N,N-dimethyl-formamide for 16h; Ambient temperature;85%
Adefovir
106941-25-7

Adefovir

ethylenediamine
107-15-3

ethylenediamine

C10H18N7O3P

C10H18N7O3P

Conditions
ConditionsYield
With hydrogenchloride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In water at 20℃;85%
Adefovir
106941-25-7

Adefovir

vitamin E
895518-38-4

vitamin E

C66H108N5O6P

C66H108N5O6P

Conditions
ConditionsYield
With triethylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; for 24h;79.36%
2-chloroethanal
107-20-0

2-chloroethanal

Adefovir
106941-25-7

Adefovir

9-(2-phosphonylmethoxyethyl)-1,N6-ethenoadenine
120139-27-7

9-(2-phosphonylmethoxyethyl)-1,N6-ethenoadenine

Conditions
ConditionsYield
In water at 40℃; for 24h; pH 4.5;78.1%
Chloromethyl pivalate
18997-19-8

Chloromethyl pivalate

Adefovir
106941-25-7

Adefovir

adefovir dipivoxyl
142340-99-6

adefovir dipivoxyl

Conditions
ConditionsYield
With triethylamine In 1-methyl-pyrrolidin-2-one at 50 - 55℃; Solvent; Reagent/catalyst; Temperature; Inert atmosphere; Large scale;78.1%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 25℃; for 24h;75%
With tetrabutylammomium bromide; triethylamine In 1-methyl-pyrrolidin-2-one at 65 - 75℃; for 2h; Temperature; Reagent/catalyst; Solvent;57.5%
Pyridine-2,6-dicarboxylic acid
499-83-2

Pyridine-2,6-dicarboxylic acid

Adefovir
106941-25-7

Adefovir

C8H12N5O4P*C7H5NO4

C8H12N5O4P*C7H5NO4

Conditions
ConditionsYield
In ethanol; water at 90℃; for 3h;75%
2,2,2-trifluoroethanol
75-89-8

2,2,2-trifluoroethanol

Adefovir
106941-25-7

Adefovir

9-(2-phosphonomethoxyethyl)adenine 2,2,2-trifluoroethyl ester

9-(2-phosphonomethoxyethyl)adenine 2,2,2-trifluoroethyl ester

Conditions
ConditionsYield
With thionyl chloride In N,N-dimethyl-formamide for 16h; Ambient temperature;74%
propan-1-ol
71-23-8

propan-1-ol

Adefovir
106941-25-7

Adefovir

9-(2-phosphonomethoxyethyl)adenine propyl ester

9-(2-phosphonomethoxyethyl)adenine propyl ester

Conditions
ConditionsYield
With thionyl chloride In N,N-dimethyl-formamide for 16h; Product distribution; Ambient temperature; various hydroxylic components under different reaction conditions;73%
With thionyl chloride In N,N-dimethyl-formamide for 16h; Ambient temperature;73%
Adefovir
106941-25-7

Adefovir

4-amino-benzoic acid
150-13-0

4-amino-benzoic acid

2C8H12N5O4P*C7H7NO2*3H2O

2C8H12N5O4P*C7H7NO2*3H2O

Conditions
ConditionsYield
With water at 90℃; for 2h;70%
2-(morpholin-4-yl)ethanol
622-40-2

2-(morpholin-4-yl)ethanol

Adefovir
106941-25-7

Adefovir

9-(2-phosphonomethoxyethyl)adenine 2-morpholinoethyl ester

9-(2-phosphonomethoxyethyl)adenine 2-morpholinoethyl ester

Conditions
ConditionsYield
With thionyl chloride In N,N-dimethyl-formamide for 16h; Ambient temperature;68%
2,2,2-tribromoethanol
75-80-9

2,2,2-tribromoethanol

Adefovir
106941-25-7

Adefovir

9-(2-phosphonomethoxyethyl)adenine 2,2,2-tribromoethyl ester

9-(2-phosphonomethoxyethyl)adenine 2,2,2-tribromoethyl ester

Conditions
ConditionsYield
With thionyl chloride In N,N-dimethyl-formamide for 48h; Ambient temperature;64%
N,N-dimethylformamide dibenzyl acetal
2016-04-8

N,N-dimethylformamide dibenzyl acetal

Adefovir
106941-25-7

Adefovir

9-(2-phosphonomethoxyethyl)adenine benzyl ester

9-(2-phosphonomethoxyethyl)adenine benzyl ester

Conditions
ConditionsYield
at 60℃; for 48h;60%
Adefovir
106941-25-7

Adefovir

ethylene glycol
107-21-1

ethylene glycol

9-(2-phosphonomethoxyethyl)adenine 2-hydroxyethyl ester

9-(2-phosphonomethoxyethyl)adenine 2-hydroxyethyl ester

Conditions
ConditionsYield
With thionyl chloride In N,N-dimethyl-formamide for 16h; Ambient temperature;57%
Adefovir
106941-25-7

Adefovir

hexan-1-ol
111-27-3

hexan-1-ol

9-(2-phosphonomethoxyethyl)adenine hexyl ester

9-(2-phosphonomethoxyethyl)adenine hexyl ester

Conditions
ConditionsYield
With thionyl chloride In N,N-dimethyl-formamide for 16h; Ambient temperature;56%
Adefovir
106941-25-7

Adefovir

3-Hydroxypropionitrile
109-78-4

3-Hydroxypropionitrile

9-(2-phosphonomethoxyethyl)adenine 2-cyanoethyl ester

9-(2-phosphonomethoxyethyl)adenine 2-cyanoethyl ester

Conditions
ConditionsYield
With thionyl chloride In N,N-dimethyl-formamide for 4h; Ambient temperature;51%
Adefovir
106941-25-7

Adefovir

glycine ethyl ester hydrochloride
5680-79-5

glycine ethyl ester hydrochloride

9-(bis(N,N'-(methoxycarbonylmethyl)phosphonamido)methoxyethyl)adenine
1041402-65-6

9-(bis(N,N'-(methoxycarbonylmethyl)phosphonamido)methoxyethyl)adenine

Conditions
ConditionsYield
With 2,2'-dipyridyldisulphide; triethylamine; triphenylphosphine In pyridine at 90℃; for 24h; Mukaiyama reaction; Inert atmosphere;51%
3,6,9,12,15,1 8-hexaoxaicosyl p-toluensulfonate

3,6,9,12,15,1 8-hexaoxaicosyl p-toluensulfonate

Adefovir
106941-25-7

Adefovir

9-[2-(phosphonomethoxy)ethyl]adenine bis(3,6,9,12,15,18-hexaoxaeicosyl) ester
1313815-78-9

9-[2-(phosphonomethoxy)ethyl]adenine bis(3,6,9,12,15,18-hexaoxaeicosyl) ester

Conditions
ConditionsYield
Stage #1: Adefovir With tetra(n-butyl)ammonium hydroxide In methanol
Stage #2: 3,6,9,12,15,1 8-hexaoxaicosyl p-toluensulfonate In N,N-dimethyl-formamide at 100℃;
50%
(aqua(diethylenetriamine)platinum(II))nitrate

(aqua(diethylenetriamine)platinum(II))nitrate

Adefovir
106941-25-7

Adefovir

(diehylenetriamine)Pt(dianion of 9-[2-(phosphonomethoxy)ethyl]adenine)*HNO3*NaNO3*H2O

(diehylenetriamine)Pt(dianion of 9-[2-(phosphonomethoxy)ethyl]adenine)*HNO3*NaNO3*H2O

Conditions
ConditionsYield
With aq. HNO3 In water aq. soln. of org. compd. slowly added to soln. of complex (pH= 1.3 adjusted with 1 M HNO3) during 3 h, stirred for 24 h at 35°C; volatiles evapd. at room temp. in N2 stream, treated twice with MeOH (12 h, ambient temp.), foltered, elem. anal.;49%
Adefovir
106941-25-7

Adefovir

dimethylformamide 1,3-butylene acetal

dimethylformamide 1,3-butylene acetal

A

9-(2-phosphonomethoxyethyl)adenine 3-hydroxybutyl ester

9-(2-phosphonomethoxyethyl)adenine 3-hydroxybutyl ester

B

[2-(6-Amino-purin-9-yl)-ethoxymethyl]-phosphonic acid mono-(3-hydroxy-1-methyl-propyl) ester

[2-(6-Amino-purin-9-yl)-ethoxymethyl]-phosphonic acid mono-(3-hydroxy-1-methyl-propyl) ester

Conditions
ConditionsYield
at 70℃; for 16h;A 48%
B n/a
(S)-(-)-1-(3'-Chlorophenyl)-1,3-Propanediol
51699-45-7

(S)-(-)-1-(3'-Chlorophenyl)-1,3-Propanediol

Adefovir
106941-25-7

Adefovir

(rac)-cis-9-{2-[4-(3-chlorophenyl)-2-oxo-1,3,2-dioxaphosphorinan-2-methyleneoxy]eth-1-yl}adenine

(rac)-cis-9-{2-[4-(3-chlorophenyl)-2-oxo-1,3,2-dioxaphosphorinan-2-methyleneoxy]eth-1-yl}adenine

(rac)-trans-9-{2-[4-(3-chlorophenyl)-2-oxo-1,3,2-dioxaphosphorinan-2-methyleneoxy]eth-1-yl}adenine

(rac)-trans-9-{2-[4-(3-chlorophenyl)-2-oxo-1,3,2-dioxaphosphorinan-2-methyleneoxy]eth-1-yl}adenine

Conditions
ConditionsYield
With pyridine; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 100℃;A 48%
B n/a
With pyridine; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 100℃;
Adefovir
106941-25-7

Adefovir

1,2,3-tri-O-acetylthreitol

1,2,3-tri-O-acetylthreitol

9-(2-phosphonomethoxyethyl)adenine 2,3,4-trihydroxy-1-butyl ester

9-(2-phosphonomethoxyethyl)adenine 2,3,4-trihydroxy-1-butyl ester

Conditions
ConditionsYield
With thionyl chloride In N,N-dimethyl-formamide for 16h; Ambient temperature;47%
octanol
111-87-5

octanol

Adefovir
106941-25-7

Adefovir

9-(2-phosphonomethoxyethyl)adenine octyl ester

9-(2-phosphonomethoxyethyl)adenine octyl ester

Conditions
ConditionsYield
With thionyl chloride In N,N-dimethyl-formamide for 16h; Ambient temperature;46%

Adefovir Chemical Properties

Molecular Structure of 9-(2-Phosphonylmethoxyethyl)adenine (CAS NO.106941-25-7):

Molecular Formula: C8H12N5O4P
Molecular Weight: 273.1857
IUPAC Name: 2-(6-Aminopurin-9-yl)ethoxymethylphosphonic acid
Synonyms of 9-(2-Phosphonylmethoxyethyl)adenine (CAS NO.106941-25-7): Adefovir [USAN:INN] ; ((2-(6-Amino-9H-purin-9-yl)ethoxy)methyl)phosphonic acid ; 9-(2-(Phosphonomethoxy)ethyl)adenine ; Adefovir ; BRN 3561094 ; DRG-0156 ; GS 0393 ; GS 393 ; GS-0393 ; N-(2-Phophonomethoxyethyl-2,6-diaminopurine) ; N-(2-Phosphonylmethoxyethyl)adenine ; PMEA ; Phosphonic acid, ((2-(6-amino-9H-purin-9-yl)ethoxy)methyl)- ; UNII-6GQP90I798
CAS NO: 106941-25-7
Classification Code: Anti-Infective Agents ; Anti-Retroviral Agents ; Antiviral ; Antiviral agents ; Enzyme Inhibitors ; Mutation data ; Nucleic Acid Synthesis Inhibitors ; Reverse Transcriptase Inhibitors
Melting point: >260°C 
Index of Refraction: 1.768
Molar Refractivity: 60.14 cm3
Molar Volume: 144.9 cm3
Surface Tension: 103.8 dyne/cm
Density: 1.88 g/cm3
Flash Point: 336.3 °C
Enthalpy of Vaporization: 98.29 kJ/mol
Boiling Point: 632.5 °C at 760 mmHg
Vapour Pressure: 7.24E-17 mmHg at 25°C

Adefovir Uses

 9-(2-Phosphonylmethoxyethyl)adenine (CAS NO.106941-25-7) can be used for antiviral.

Adefovir Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD intravenous > 1gm/kg (1000mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Antimicrobial Agents and Chemotherapy. Vol. 40, Pg. 1072, 1996.
mouse LDLo intraperitoneal 1600mg/kg (1600mg/kg)   Antimicrobial Agents and Chemotherapy. Vol. 40, Pg. 1072, 1996.

Adefovir Safety Profile

Mutation data reported. When heated to decomposition it emits toxic vapors of NOx and POx.

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