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Name	Adefovir dipivoxil	EINECS	200-001-8
CAS No.	142340-99-6	Density	1.35 g/cm³
PSA	176.79000	LogP	3.28370
Solubility	N/A	Melting Point	98-102 °C
Formula	C₂₀H₃₂N₅O₈P	Boiling Point	641 °C at 760 mmHg
Molecular Weight	501.477	Flash Point	341.5 °C
Transport Information	N/A	Appearance	It has broad-spectrum antiviral activity
Safety	36/37	Risk Codes	20/21/22
Molecular Structure		Hazard Symbols	Xi
Synonyms	9-(2-((-Bis((pivaloyloxy)methoxy)phosphinyl)methoxy)ethyl)adenine;Adefovir pivoxil;Bis(POM)-PMEA;Preveon;Propanoic acid,2,2-dimethyl-,[[[2-(6-amino- 9H-purin-9-yl)ethoxy]methyl]phosphinylidene]- bis(oxymethylene) ester;Hepsera (TN);[2-(6-aminopurin-9-yl)ethoxymethyl-(2,2-dimethylpropanoyloxymethoxy)phosphoryl]oxymethyl 2,2-dimethylpropanoate;Bis(pivaloyloxymethyl)-9-(2-phosphonylmethoxyethyl)adenine;Adefovir pivoxil (JAN);Phosphonyl Methoxy Ethyl Adenine;Adefovirdipivoxil;Adefovir dipivoxyl;	Article Data	19

Adefovir dipivoxil Synthetic route

: 18997-19-8
Chloromethyl pivalate

: 106941-25-7
Adefovir

: 142340-99-6
adefovir dipivoxyl

Conditions

Conditions	Yield
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%

: [[2-chloroethoxy]methyl]phosphonic acid bis(pivaloyloxymethyl) ester

: 73-24-5
7H-purin-6-ylamine

: 142340-99-6
adefovir dipivoxyl

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 90 - 95℃; for 9h; Large scale;	46.18%

: chloropentyl pivalate

: 106941-25-7
Adefovir

: 142340-99-6
adefovir dipivoxyl

Conditions

Conditions	Yield
With triethylamine In 1-methyl-pyrrolidin-2-one at 30 - 60℃; for 16h; Reagent/catalyst;	32.6%

: 2,2-Dimethyl-propionic acid (2,2-dimethyl-propionyloxymethoxy)-[2-(6-{[(4-methoxy-phenyl)-diphenyl-methyl]-amino}-purin-9-yl)-ethoxymethyl]-phosphinoyloxymethyl ester

: 142340-99-6
adefovir dipivoxyl

Conditions

Conditions	Yield
With acetic acid In methanol for 12h; Ambient temperature; Yield given;

: 53064-79-2
iodomethyl pivaloate

: 142340-99-6
adefovir dipivoxyl

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine / 36 h / Ambient temperature 2: aq. AcOH / methanol / 12 h / Ambient temperature View Scheme

: 153235-86-0
N6-(4-monomethoxytrityl)-9-(2-phosphonomethoxyethyl)adenine

: 142340-99-6
adefovir dipivoxyl

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine / 36 h / Ambient temperature 2: aq. AcOH / methanol / 12 h / Ambient temperature View Scheme

: 922494-99-3
N4-dimethylaminomethyledino-9-(2-phosphonomethoxyethyl)adenine di(pivaloyloxymethyl) ester

: 142340-99-6
adefovir dipivoxyl

Conditions

Conditions	Yield
Stage #1: N4-dimethylaminomethylideno-9-(2-phosphonomethoxyethyl)adinine di(pivaloyloxymethyl) ester With acetic acid In water at 25 - 55℃; for 3h; Stage #2: With triethylamine In water; ethyl acetate pH=7.5;
Stage #1: N4-dimethylaminomethylideno-9-(2-phosphonomethoxyethyl)adinine di(pivaloyloxymethyl) ester With water; acetic acid at 25 - 55℃; for 3h; Stage #2: With triethylamine In water; ethyl acetate pH=7.5;

: 18997-19-8
Chloromethyl pivalate

: 106941-25-7
Adefovir

A: 323201-04-3
9-[2-({bis[(pivaloyloxy)methoxy]phosphinyl}methoxy)ethyl]-6-[(hydroxymethyl)amino]purine

B: 142340-99-6
adefovir dipivoxyl

Conditions

Conditions	Yield
In dimethyl sulfoxide; triethylamine at 43℃; for 4h;
Stage #1: Chloromethyl pivalate; Adefovir With triethylamine In dimethyl sulfoxide at 40℃; for 5h; Stage #2: With water In dichloromethane; dimethyl sulfoxide at 10 - 20℃; for 0.0833333h; Product distribution / selectivity;

: 66224-66-6, 66224-67-7, 66224-68-8, 66224-69-9, 134434-48-3, 134434-49-4, 134454-76-5, 134461-75-9
adenine

: 142340-99-6
adefovir dipivoxyl

Conditions

Conditions	Yield
Multi-step reaction with 3 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 3.1: triethylamine; tetrabutylammomium bromide / ethyl acetate; N,N-dimethyl-formamide / 1 h / 25 - 35 °C 3.2: 25 - 35 °C View Scheme
Multi-step reaction with 4 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 16 h / 60 °C 2.1: ammonia / methanol / 14 h 3.1: magnesium 2-methylpropan-2-olate / N,N-dimethyl-formamide / 1 h / 20 °C / Inert atmosphere 3.2: 20 h / 35 °C / Inert atmosphere 4.1: sodium bromide; 1-methyl-pyrrolidin-2-one; chloro-trimethyl-silane / 12 h / 60 °C / Inert atmosphere 4.2: 6 h / 60 °C View Scheme
Multi-step reaction with 4 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 4: triethylamine / 1-methyl-pyrrolidin-2-one / 16 h / 30 - 60 °C View Scheme

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

: 142340-99-6
adefovir dipivoxyl

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: water; hydrogen bromide / 4 h / 90 - 95 °C 1.2: 25 - 30 °C / pH 2.8 2.1: triethylamine; tetrabutylammomium bromide / ethyl acetate; N,N-dimethyl-formamide / 1 h / 25 - 35 °C 2.2: 25 - 35 °C View Scheme

Adefovir dipivoxil Chemical Properties

Molecular Structure of Adefovir dipivoxil (CAS NO. 142340-99-6):

IUPAC Name: [2-(6-Aminopurin-9-yl)ethoxymethyl-(2,2-dimethylpropanoyloxymethoxy)phosphoryl]oxymethyl 2,2-dimethylpropanoate
Molecular Formula: C₂₀H₃₂N₅O₈P
Molecular Weight: 501.470541 g/mol
Index of Refraction: 1.569
Molar Refractivity: 120.96 cm³
Molar Volume: 369.1 cm³
Surface Tension: 51.1 dyne/cm
Density: 1.35 g/cm³
Flash Point: 341.5 °C
Enthalpy of Vaporization: 94.62 kJ/mol
Boiling Point: 641 °C at 760 mmHg
Vapour Pressure: 2.52E-16 mmHg at 25 °C
Melting Point: 98-102 °C
Storage Temp.: −20 °C
EINECS: 200-001-8
Product Categories: Active Pharmaceutical Ingredients; Adefovir

Adefovir dipivoxil Production

Adefovir dipivoxil can be obtained by two similar ways: 1) The reaction of adenine (I) with 2-(diisopropoxyphosphorylmethoxy)ethyl methanesulfonate (II) by means of cesium carbonate in DMF gives the expected condensation product (III), which is converted into the phosphonic acid (IV) by treatment with trimethylsilyl bromide in acetonitrile (1). Finally, this compound is condensed with chloromethyl pivalate (V) by means of N,N'-dicyclohexylmorpholine-4-carboxamidine in DMF. 2) The final condensation of the phosphonic acid (IV) can also be performed with iodomethyl pivalate (VI) in pyridine.

Adefovir dipivoxil Safety Profile

Safety Information of Adefovir dipivoxil (CAS NO. 142340-99-6):
Hazard Codes: Xn Harmful
Risk Statements: 20/21/22
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed
Safety Statements: 36/37
S36/37:Wear suitable protective clothing and gloves

Adefovir dipivoxil Specification

Adefovir dipivoxil is also called (((2-(6-Amino-9H-purin-9-yl)ethoxy)methyl)phosphinylidene)bis(oxymethylene) 2,2-dimethylpropanoate ; ((2-(6-Amino-9H-purin-9-yl)ethoxy)methyl)phosphonic acid, diester with hydroxymethyl pivalate ; 9-(2-((-Bis((pivaloyloxy)methoxy)phosphinyl)methoxy)ethyl)adenine ; 9-(2-((Bis((pivaloyloxy)methoxy)phosphinyl)methoxy)ethyl)adenine ; Adefovir dipivoxil ; GS 840 ; GS-0840 ; Hepsera ; Preveon ; Propanoic acid, 2,2-dimethyl-, (((2-(6-amino-9H-purin-9-yl)ethoxy)methyl)phosphinylidene)bis(oxymethylene) ester ; UNII-U6Q8Z01514 .

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