Voriconazole supplier | CasNO.137234-62-9

Name
Voriconazole
EINECS 629-701-5
CAS No. 137234-62-9
Article Data35
CAS DataBase
Density 1.42 g/cm³
Solubility
Melting Point 127-130 °C
Formula C₁₆H₁₄F₃N₅O
Boiling Point 508.6 °C at 760 mmHg
Molecular Weight 349.315
Flash Point 261.4 °C
Transport Information
Appearance cyrstalline solid
Safety 26-36
Risk Codes 22-36/38
Molecular Structure
Hazard Symbols Xn
Synonyms 4-Pyrimidineethanol, alpha-(2,4-difluorophenyl)-5-fluoro-beta-methyl-alpha-(1H-1,2,4-triazol-1-ylmethyl)-,(alphaR,betaS)-;DRG-0301;UK-109,496;UNII-JFU09I87TR;Vfend;VRC;
PSA 76.72000
LogP 2.17690

Synthetic route

: 188416-34-4, 137234-71-0
(2R,3S)-2-(2,4-difluorophenyl)-3-(5-fluoro-4-pyrimidinyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol (1R)-10-camphorsulfonate

: 137234-62-9
voriconazole

Conditions

Conditions	Yield
With sodium hydrogencarbonate In dichloromethane for 0.5h;	92%
With sodium hydrogencarbonate In water; ethyl acetate	90.47%
With sodium hydroxide In water at 45 - 55℃; for 2.5h; Product distribution / selectivity;	87.22%

: (2R,3S)-2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol R-(-)-10-camphorsulfonate

: 137234-62-9
voriconazole

Conditions

Conditions	Yield
With sodium hydroxide In dichloromethane; water pH=11 - 12;	92%

: voriconazole L-camphorsulfate

: 137234-62-9
voriconazole

Conditions

Conditions	Yield
With sodium hydrogencarbonate In dichloromethane for 0.5h;	92%
With sodium hydroxide In dichloromethane; water at 15 - 25℃; pH=10 - 11;

: voriconazole L-camphor sulfonate

: 137234-62-9
voriconazole

Conditions

Conditions	Yield
With sodium hydrogencarbonate In dichloromethane for 0.5h;	90.8%
With sodium hydroxide In dichloromethane; water pH=12.3; Product distribution / selectivity; Alkaline aqueous solution; Industry scale;	72%
With sodium hydroxide In dichloromethane; water pH=11; Product distribution / selectivity; Alkaline aqueous solution;

: C26H28F3N5O5S

: 137234-62-9
voriconazole

Conditions

Conditions	Yield
With 5%-palladium/activated carbon; hydrogen In ethanol under 760.051 Torr;	86.3%

: 188416-38-8
(2R,3S)-3-(6-chloro-5-fluoropyrimidin-4-yl)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1 yl)butan-2-ol

: 137234-62-9
voriconazole

Conditions

Conditions	Yield
With palladium 10% on activated carbon; potassium formate In ethanol; water at 30℃; for 1h; Temperature; Reagent/catalyst; Inert atmosphere;	84.9%
With palladium 10% on activated carbon; hydrogen; sodium acetate In water; toluene at -21 - 40℃; under 3750.38 Torr; for 22h;

: 848469-32-9
(2R,3S)-2-(2,4-diflurophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1yl)butan-2-ol R-(-)-10-camphor sulphonate salt

: 137234-62-9
voriconazole

Conditions

Conditions	Yield
With sodium carbonate In dichloromethane; water at 20℃; for 0.333333h; pH=~ 10; Product distribution / selectivity;	76%
With sodium hydroxide In dichloromethane; water pH=11 - 12; Product distribution / selectivity;

: (2R,3S)-2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol ((1R,4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1yl)methanesulfonate

: 137234-62-9
voriconazole

Conditions

Conditions	Yield
With water In ethanol at 32.5℃; Concentration; Solvent; Temperature;	76%

: 2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butane-2-ol

: 137234-62-9
voriconazole

Conditions

Conditions	Yield
With [(1R)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonic acid In methanol; acetone for 2h; Reflux;	43%
With (R)-10-camphorsulfonic acid In methanol; acetone at 0 - 5℃; Resolution of racemate;	40.1%
Multi-step reaction with 2 steps 1: acetone; methanol / 15 h / -20 - 25 °C 2: sodium hydroxide / dichloromethane; water / 0.25 h / pH 11 - 14 View Scheme
Multi-step reaction with 2 steps 1: methanol; acetone / Reflux 2: sodium hydroxide / water; dichloromethane / pH 11 View Scheme

: 1602485-93-7
5-fluoro-4-vinylpyrimidine

: 86404-63-9
1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazolyl)ethanone

: 137234-62-9
voriconazole

Conditions

Conditions	Yield
With CuF(PPh3)3 methanol solvate; (R)-(−)-1-[(R)-2-(2′-diphenylphosphinophenyl)ferrocenyl]ethylbis(di-3,5-trifluoromethylphenyl)phosphine at 0℃; for 21.5h; Reagent/catalyst; Inert atmosphere;	40%

: 188416-35-5
3-(6-chloro-5-fluoropyrimidin-4-yl)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol

: 137234-62-9
voriconazole

Conditions

Conditions	Yield
Stage #1: 3-(6-chloro-5-fluoropyrimidin-4-yl)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol With 5%-palladium/activated carbon; hydrogen; sodium acetate In methanol at 25℃; under 760.051 Torr; Stage #2: With [(1R)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonic acid In methanol; acetone for 2h; Reflux;	35%
Multi-step reaction with 3 steps 1.1: sodium acetate / ethyl acetate; water / 0.5 h / 25 - 30 °C 1.2: 25 - 30 °C / 3677.86 Torr 1.3: 0.5 h / 20 - 25 °C 2.1: acetone; methanol / 15 h / -20 - 25 °C 3.1: sodium hydroxide / dichloromethane; water / 0.25 h / pH 11 - 14 View Scheme
Multi-step reaction with 4 steps 1.1: hydrogen; sodium acetate / palladium 10% on activated carbon / ethyl acetate; water / 25 - 30 °C / 3677.86 Torr 1.2: 0.5 h / 20 - 25 °C 1.3: 12.5 h / 25 - 30 °C 2.1: sodium hydroxide / dichloromethane; water / 0.5 h / pH 9 - 12 3.1: acetone; methanol / 15 h / -20 - 25 °C 4.1: sodium hydroxide / dichloromethane; water / 0.25 h / pH 11 - 14 View Scheme
Multi-step reaction with 4 steps 1.1: hydrogen; sodium acetate; sodium carbonate / palladium 10% on activated carbon / ethyl acetate; water / 25 - 30 °C / 3677.86 Torr 1.2: 0.5 h / 20 - 25 °C 1.3: 10 - 25 °C 2.1: potassium carbonate / dichloromethane; water / 0.5 h / pH 8 - 10 3.1: acetone; methanol / 15 h / -20 - 25 °C 4.1: sodium hydroxide / dichloromethane; water / 0.25 h / pH 11 - 14 View Scheme

: 288-88-0
1,2,4-Triazole

: 1474024-68-4
4-((S)-1-((R)-2-(2,4-difluorophenyl)oxirane-2-yl)ethyl)-5-fluoropyrimidine

A: 1028563-65-6
(2R,3S)-2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(4H-1,2,4-triazol-4-yl)butan-2-ol

B: (2S,3R)-2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol

C: 137234-62-9
voriconazole

Conditions

Conditions	Yield
In ethanol at 80℃; for 18h; Inert atmosphere;	A 27% B n/a C n/a

...Expand

: 1003706-87-3
4-bromo-5-fluoro-pyrimidine

: (3S)-2-(2,4-difluorophenyl)-3-methyl-[(1H-1,2,4-triazol-1-yl)methyl]oxirane

: 137234-62-9
voriconazole

Conditions

Conditions	Yield
In tetrahydrofuran at -70 - 30℃; for 25h; Temperature; Inert atmosphere;	26.3%

: (3S)-2-(2,4-difluorophenyl)-3-methyl-[(1H-1,2,4-triazol-1-yl)methyl]oxirane

: 347418-42-2
2,4-dichloro-5-fluoropyrimidine

: 137234-62-9
voriconazole

Conditions

Conditions	Yield
In tetrahydrofuran at -70 - 30℃; for 25h; Temperature; Inert atmosphere;	20.7%

: (2R,3S/2S,3R)-3-(4-chloro-5-fluoropyrimidin-6-yl)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol

A: (2S,3R)-2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol

B: 137234-62-9
voriconazole

Conditions

Conditions	Yield
With hydrogen; sodium acetate; palladium on activated charcoal In ethanol at 20℃;

: 759-67-1
2-fluoro-3-oxopentanoic acid ethyl ester

: 137234-62-9
voriconazole

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 1) MeONa, MeOH 2: POCl3 / Heating 3: LDA / tetrahydrofuran 4: H2, AcONa / Pd/C / ethanol / 20 °C View Scheme

: 137234-87-8
6-Ethyl-5-fluoropyrimidin-4(3H)-one

: 137234-62-9
voriconazole

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: POCl3 / Heating 2: LDA / tetrahydrofuran 3: H2, AcONa / Pd/C / ethanol / 20 °C View Scheme

: 137234-74-3
4-chloro-5-fluoro-6-ethylpyrimidine

: 137234-62-9
voriconazole

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: LDA / tetrahydrofuran 2: H2, AcONa / Pd/C / ethanol / 20 °C View Scheme
Multi-step reaction with 4 steps 1.1: diisopropylamine; n-butyllithium / n-heptane; hexane; tetrahydrofuran / 0.25 h / -80 - -70 °C / Inert atmosphere 1.2: 2 h / -80 - -55 °C 1.3: -70 - -10 °C 2.1: sodium acetate / ethyl acetate; water / 0.5 h / 25 - 30 °C 2.2: 25 - 30 °C / 3677.86 Torr 2.3: 0.5 h / 20 - 25 °C 3.1: acetone; methanol / 15 h / -20 - 25 °C 4.1: sodium hydroxide / dichloromethane; water / 0.25 h / pH 11 - 14 View Scheme
Multi-step reaction with 5 steps 1.1: diisopropylamine; n-butyllithium / n-heptane; hexane; tetrahydrofuran / 0.25 h / -80 - -70 °C / Inert atmosphere 1.2: 2 h / -80 - -55 °C 1.3: -70 - -10 °C 2.1: hydrogen; sodium acetate / palladium 10% on activated carbon / ethyl acetate; water / 25 - 30 °C / 3677.86 Torr 2.2: 0.5 h / 20 - 25 °C 2.3: 12.5 h / 25 - 30 °C 3.1: sodium hydroxide / dichloromethane; water / 0.5 h / pH 9 - 12 4.1: acetone; methanol / 15 h / -20 - 25 °C 5.1: sodium hydroxide / dichloromethane; water / 0.25 h / pH 11 - 14 View Scheme

: 321589-01-9
2-(2,4difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)-butan-2-ol-R(-)-10-camphor sulphonate

: 137234-62-9
voriconazole

Conditions

Conditions	Yield
With sodium hydroxide In dichloromethane; water at 25 - 35℃; pH=11 - 12; Alkaline conditions;

: 188416-28-6
1-(4-chloro-5-fluoropyrimidin-6-yl)bromoethane

: 86404-63-9
1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazolyl)ethanone

A: (2S,3R)-2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol

B: 137234-62-9
voriconazole

Conditions

Conditions	Yield
Stage #1: 1-(4-chloro-5-fluoropyrimidin-6-yl)bromoethane; 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazolyl)ethanone With zinc(II) chloride; zinc In tetrahydrofuran at -5 - 5℃; for 1h; Stage #2: With ammonium formate; zinc In methanol at 20℃; for 16h; Stage #3: Product distribution / selectivity; Heating / reflux;

...Expand

: 3-(6-chloro-5-fluoro-4-pyrimidinyl)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol hydrochloride

A: (2S,3R)-2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol

B: 137234-62-9
voriconazole

Conditions

Conditions	Yield
With ammonium formate; zinc In methanol Product distribution / selectivity;

: C10H16O4S*C16H14F3N5O

A: (2S,3R)-2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol

B: 137234-62-9
voriconazole

Conditions

Conditions	Yield
With sodium hydrogencarbonate In water; ethyl acetate at 20 - 25℃;

: 182230-43-9
2-(2,4-Difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol

: 137234-62-9
voriconazole

Conditions

Conditions	Yield
Stage #1: 2-(2,4-Difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol With (R)-10-camphorsulfonic acid In methanol; acetone at 25 - 60℃; for 2h; Stage #2: With sodium hydroxide In dichloromethane; water; isopropyl alcohol at 20 - 30℃; pH=12 - 13; Product distribution / selectivity;
With (1S)-10-camphorsulfonic acid In methanol; acetone at 20 - 30℃; for 3.5h; Reflux;
Multi-step reaction with 2 steps 1: sodium hydroxide / water / 3 h / 45 °C 2: camphor-10-sulfonic acid / methanol; acetone View Scheme

: 1289559-75-6
C6H5FN2O

: 137234-62-9
voriconazole

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: sodium tetrahydroborate / ethanol / 5 h 2.1: triethylamine / dmap / dichloromethane / 20 - 30 °C 3.1: zinc; zinc(II) chloride / tetrahydrofuran / 0 - 30 °C 4.1: (R)-10-camphorsulfonic acid / acetone; methanol / 2 h / 25 - 60 °C 4.2: 20 - 30 °C / pH 12 - 13 View Scheme

: 1289559-65-4
1-(2,6-dichloro-5-fluoropyrimidin-4-yl)ethanone

: 137234-62-9
voriconazole

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: hydrogen; sodium acetate / palladium on activated carbon / ethanol / 25 °C 2.1: sodium tetrahydroborate / ethanol / 5 h 3.1: triethylamine / dmap / dichloromethane / 20 - 30 °C 4.1: zinc; zinc(II) chloride / tetrahydrofuran / 0 - 30 °C 5.1: (R)-10-camphorsulfonic acid / acetone; methanol / 2 h / 25 - 60 °C 5.2: 20 - 30 °C / pH 12 - 13 View Scheme

: 1289559-66-5
1-(5-fluoropyrimidin-4-yl)ethanol

: 137234-62-9
voriconazole

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: triethylamine / dmap / dichloromethane / 20 - 30 °C 2.1: zinc; zinc(II) chloride / tetrahydrofuran / 0 - 30 °C 3.1: (R)-10-camphorsulfonic acid / acetone; methanol / 2 h / 25 - 60 °C 3.2: 20 - 30 °C / pH 12 - 13 View Scheme

: 51336-94-8
2-chloro-1-(2,4-dichlorophenyl)ethanone

: 137234-62-9
voriconazole

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: potassium carbonate / tetrahydrofuran / 7 h / 20 °C 2: lead; zinc; iodine / tetrahydrofuran / -15 - 20 °C / Inert atmosphere 3: ammonium formate / palladium on carbon / toluene / 3 h / 80 °C 4: acetone; methanol / 1 h / Reflux 5: sodium hydrogencarbonate / dichloromethane / 0.5 h View Scheme
Multi-step reaction with 5 steps 1: potassium carbonate / tetrahydrofuran / 7 h / 20 °C 2: lead; zinc; iodine / tetrahydrofuran / 2 h / -15 - -10 °C / Inert atmosphere 3: ammonium formate / 10% palladium on charcoal / toluene / 3 h / 80 °C 4: acetone; methanol / 1 h / Reflux 5: sodium hydrogencarbonate / dichloromethane / 0.5 h View Scheme

: 137234-87-8
6-ethyl-5-fluoro-4-hydroxypyrimidine

: 137234-62-9
voriconazole

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: triethylamine / dichloromethane / 5 h / 20 °C 2: 2,2'-azobis(isobutyronitrile); N-Bromosuccinimide / dichloromethane / 12 h / 45 - 50 °C 3: lead; zinc; iodine / tetrahydrofuran / -15 - 20 °C / Inert atmosphere 4: ammonium formate / palladium on carbon / toluene / 3 h / 80 °C 5: acetone; methanol / 1 h / Reflux 6: sodium hydrogencarbonate / dichloromethane / 0.5 h View Scheme
Multi-step reaction with 5 steps 1.1: triethylamine / dichloromethane / 5 - 10 °C 1.2: 8 h / 10 - 55 °C / Reflux 1.3: 0.5 h / 15 - 20 °C 2.1: diisopropylamine; n-butyllithium / n-heptane; hexane; tetrahydrofuran / 0.25 h / -80 - -70 °C / Inert atmosphere 2.2: 2 h / -80 - -55 °C 2.3: -70 - -10 °C 3.1: sodium acetate / ethyl acetate; water / 0.5 h / 25 - 30 °C 3.2: 25 - 30 °C / 3677.86 Torr 3.3: 0.5 h / 20 - 25 °C 4.1: acetone; methanol / 15 h / -20 - 25 °C 5.1: sodium hydroxide / dichloromethane; water / 0.25 h / pH 11 - 14 View Scheme
Multi-step reaction with 6 steps 1.1: triethylamine / dichloromethane / 5 - 10 °C 1.2: 8 h / 10 - 55 °C / Reflux 1.3: 0.5 h / 15 - 20 °C 2.1: diisopropylamine; n-butyllithium / n-heptane; hexane; tetrahydrofuran / 0.25 h / -80 - -70 °C / Inert atmosphere 2.2: 2 h / -80 - -55 °C 2.3: -70 - -10 °C 3.1: hydrogen; sodium acetate / palladium 10% on activated carbon / ethyl acetate; water / 25 - 30 °C / 3677.86 Torr 3.2: 0.5 h / 20 - 25 °C 3.3: 12.5 h / 25 - 30 °C 4.1: sodium hydroxide / dichloromethane; water / 0.5 h / pH 9 - 12 5.1: acetone; methanol / 15 h / -20 - 25 °C 6.1: sodium hydroxide / dichloromethane; water / 0.25 h / pH 11 - 14 View Scheme

: 1237496-99-9
6-ethyl-5-fluoropyrimidin-4-yl methanesulfonate

: 137234-62-9
voriconazole

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 2,2'-azobis(isobutyronitrile); N-Bromosuccinimide / dichloromethane / 12 h / 45 - 50 °C 2: lead; zinc; iodine / tetrahydrofuran / -15 - 20 °C / Inert atmosphere 3: ammonium formate / palladium on carbon / toluene / 3 h / 80 °C 4: acetone; methanol / 1 h / Reflux 5: sodium hydrogencarbonate / dichloromethane / 0.5 h View Scheme
Multi-step reaction with 5 steps 1: 2,2'-azobis(isobutyronitrile); N-Bromosuccinimide / dichloromethane / 12 h / 45 - 50 °C 2: lead; zinc; iodine / tetrahydrofuran / 2 h / -15 - -10 °C / Inert atmosphere 3: ammonium formate / 10% palladium on charcoal / toluene / 3 h / 80 °C 4: acetone; methanol / 1 h / Reflux 5: sodium hydrogencarbonate / dichloromethane / 0.5 h View Scheme

: 150994-82-4
4-((1,3-bis(octanoyloxy)propan-2-yl)oxy)-4-oxobutanoic acid

: 137234-62-9
voriconazole

: 4-((1,3-bis(octanoyloxy)propan-2-yl)oxy)-4-oxobutanoate 4-((2S,3R)-3-(2,4-difluorophenyl)-3-hydroxy-4-(1H-1,2,4-triazol-1-yl)butan-2-yl)-5-fluoropyrimidin-1-ium

Conditions

Conditions	Yield
In acetonitrile at 50℃; for 6h;	100%

: (2E)-4-((1,3-bis(dodecanoyloxy)propan-2-yl)oxy)-4-oxobut-2-enoic acid

: 137234-62-9
voriconazole

: (2E)-4-((1,3-bis(dodecanoyloxy)propan-2-yl)oxy)-4-oxobut-2-enoate 4-((2S,3R)-3-(2,4-difluorophenyl)-3-hydroxy-4-(1H-1,2,4-triazol-1-yl)butan-2-yl)-5-fluoropyrimidin-1-ium

Conditions

Conditions	Yield
In acetonitrile at 50℃; for 3h;	100%

: 137234-62-9
voriconazole

: voriconazole hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In water at 20℃; for 1h;	100%

: 56456-50-9
(2-chloro-6-fluorophenyl)methanol

: 137234-62-9
voriconazole

: 194798-93-1
Bis(2-chloro-6-fluorobenzyl) (2R,3S)-2-(2,4-difluorophenyl)-3-(5-fluoro-4-pyrimidinyl)-1-(1H-1,2,4-triazol-1-yl)-2-butyl phosphate

Conditions

Conditions	Yield
With 1-methyl-1H-imidazole; anhydrous phosphorus trichloride; dihydrogen peroxide In dichloromethane; tert-butyl methyl ether; water	88%

: 137234-62-9
voriconazole

: 1620283-07-9
C16H13F3N6O3

Conditions

Conditions	Yield
With sulfuric acid; nitric acid at 20℃; for 3h;	88%
With sulfuric acid; nitric acid at 0 - 20℃; for 3h;	77%

: C9H16ClNO5

: 137234-62-9
voriconazole

: C20H22F3N6O4(1+)*I(1-)

Conditions

Conditions	Yield
Stage #1: C9H16ClNO5; voriconazole With potassium iodide In acetonitrile for 15h; Reflux; Stage #2: With hydrogenchloride; water In methanol at 50 - 55℃; for 20h; Stage #3: In methanol; tert-butyl methyl ether at 10 - 65℃; for 18h;	87%

: 137234-62-9
voriconazole

: C16H14F3N5O*HNO3

Conditions

Conditions	Yield
With nitric acid In methanol; water	86.62%

: 432037-32-6
chloromethyl 2-methoxyethyl carbonate

: 137234-62-9
voriconazole

: C21H23F3N5O5(1+)*Cl(1-)

Conditions

Conditions	Yield
In acetonitrile for 10h; Reflux;	85%

: 432037-32-6
chloromethyl 2-methoxyethyl carbonate

: 137234-62-9
voriconazole

: C21H23F3N5O5(1+)*Cl(1-)

Conditions

Conditions	Yield
In acetonitrile for 12h; Reflux;	80%

: 431894-46-1
chloromethyl 2-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)ethyl carbonate

: 137234-62-9
voriconazole

: C38H56F3N5O15(2+)*2Cl(1-)

Conditions

Conditions	Yield
In acetonitrile for 14h; Reflux;	79%

: 137234-62-9
voriconazole

: voriconazole hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In methanol; water	78.62%

: 79-31-2
isobutyric Acid

: 137234-62-9
voriconazole

A: (2R,3S)-2-(2,4-difluorophenyl)-3-(5-fluoro-6-isopropylpyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol

B: (2R,3S)-2-(2,4-difluorophenyl)-3-(5-fluoro-2,6-diisopropylpyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol

Conditions

Conditions	Yield
With bis-[(trifluoroacetoxy)iodo]benzene; 9-mesityl-10-methylacridinium ion In acetonitrile at 20℃; Irradiation;	A 77% B 11%

...Expand

: 76-05-1
trifluoroacetic acid

: 137234-62-9
voriconazole

: (2R,3S)-2-(5-bromo-2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol trifluoroacetic acid

Conditions

Conditions	Yield
With N-Bromosuccinimide for 16h; Inert atmosphere;	73%

: potassium trifluoro(isopropenyl)borate(1-)

: 137234-62-9
voriconazole

: (2R,3S)-2-(2,4-difluorophenyl)-3-(5-fluoro-6-isopropylpyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol

Conditions

Conditions	Yield
With N,N,N,N-tetraethylammonium tetrafluoroborate; trifluoroacetic acid; 9-(2-mesityl)-10-methylacridinium perchlorate In water; acetonitrile at 20℃; for 10h; Inert atmosphere; Schlenk technique; Irradiation; regioselective reaction;	72%

: C9H17ClN2O4

: 137234-62-9
voriconazole

: C20H23F3N7O3(1+)*I(1-)

Conditions

Conditions	Yield
Stage #1: C9H17ClN2O4; voriconazole With potassium iodide In acetonitrile for 15h; Reflux; Stage #2: With hydrogenchloride; water In methanol at 50 - 55℃; for 20h; Stage #3: In methanol; tert-butyl methyl ether at 10 - 65℃; for 15h;	70%

: 3144-16-9
(1S)-10-camphorsulfonic acid

: 137234-62-9
voriconazole

: 848469-32-9
(2R,3S)-2-(2,4-diflurophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1yl)butan-2-ol R-(-)-10-camphor sulphonate salt

Conditions

Conditions	Yield
In methanol; acetone at 30 - 50℃; for 1.33333h; Heating / reflux;	65%

: C23H43ClN4O8

: 137234-62-9
voriconazole

: C24H33F3N9O3(1+)*I(1-)

Conditions

Conditions	Yield
Stage #1: C23H43ClN4O8; voriconazole With potassium iodide In acetonitrile for 15h; Reflux; Stage #2: With hydrogenchloride; water In methanol at 50 - 55℃; for 20h; Stage #3: In methanol; tert-butyl methyl ether at 10 - 65℃; for 18h;	65%

: 1402915-09-6
chloromethyl (2-methoxyethyl)carbamate

: 137234-62-9
voriconazole

: C21H24F3N6O4(1+)*I(1-)

Conditions

Conditions	Yield
Stage #1: chloromethyl (2-methoxyethyl)carbamate; voriconazole With potassium iodide In acetonitrile for 15h; Reflux; Stage #2: In methanol; tert-butyl methyl ether at 10 - 65℃; for 20h;	63%

: 137234-62-9
voriconazole

: 98-89-5
Cyclohexanecarboxylic acid

: (2R,3S)-3-(6-cyclohexyl-5-fluoropyrimidin-4-yl)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol

Conditions

Conditions	Yield
With hydrogenchloride; cerium(III) chloride heptahydrate; tetrabutyl-ammonium chloride In 2,2,2-trifluoroethanol; water for 17h; Schlenk technique; Inert atmosphere; Electrochemical reaction; Irradiation;	60%

: potassium trifluoro(isopropenyl)borate(1-)

: 76-05-1
trifluoroacetic acid

: 137234-62-9
voriconazole

: (2R,3S)-2-(2,4-difluorophenyl)-3-(5-fluoro-6-isopropylpyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol trifluoroacetic acid

Conditions

Conditions	Yield
Stage #1: potassium trifluoro(isopropenyl)borate(1-); voriconazole With manganese triacetate; acetic acid In water at 50℃; for 18h; Inert atmosphere; Stage #2: trifluoroacetic acid In water; acetonitrile Inert atmosphere;	58%

...Expand

: silver perchlorate

: 137234-62-9
voriconazole

: Ag(1+)*ClO4(1-)*2C16H14F3N5O

Conditions

Conditions	Yield
In ethanol; water	58%

Voriconazole Chemical Properties

Molecular structure of Voriconazole (CAS NO.137234-62-9) is:

Product Name: Voriconazole
CAS Registry Number: 137234-62-9
IUPAC Name: (2R,3S)-2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1,2,4-triazol-1-yl)butan-2-ol
Molecular Weight: 349.31047 [g/mol]
Molecular Formula: C₁₆H₁₄F₃N₅O
XLogP3-AA: 1.5
H-Bond Donor: 1
H-Bond Acceptor: 8
Melting Point: 127-130 °C
Surface Tension: 45.1 dyne/cm
Density: 1.42 g/cm³
Flash Point: 261.4 °C
Enthalpy of Vaporization: 82.02 kJ/mol
Boiling Point: 508.6 °C at 760 mmHg
Vapour Pressure: 3.63E-11 mmHg at 25°C
Product Categories: API; Antifungal (Systemic); Inhibitors; Intermediates & Fine Chemicals; Pharmaceuticals

Voriconazole History

London, UK, 16 December 2008 - The effectiveness of voriconazole in combating fungal infections has been confirmed by a new study to be featured in the International Journal of Antimicrobial Agents ，published by Elsevier.

Voriconazole Uses

Voriconazole (CAS NO.137234-62-9) is generally used to treat serious, invasive fungal infections. These are generally seen in patients who are immunocompromised, and include invasive candidiasis, invasive aspergillosis, and certain emerging fungal infections.

Voriconazole Toxicity Data With Reference

The most common side effects associated with voriconazole(137234-62-9) include transient visual disturbances, fever, rash, vomiting, nausea, diarrhea, headache, sepsis, peripheral edema, abdominal pain, and respiratory disorder.This medication may also cause the skin to peel easily. It is best to apply lotion and/or coconut oil to help with this side effect.

Voriconazole Safety Profile

Safty information about Voriconazole (CAS NO.137234-62-9) is:
Hazard Codes: Harmful Xn
Risk Statements: 22-36/38
R22:Harmful if swallowed.
R36/38:Irritating to eyes and skin.
Safety Statements: 26-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.

Voriconazole Specification

Voriconazole , its cas register number is 137234-62-9. It also can be called Voriconazole [USAN:INN:BAN] ; (alphaR,betaS)-alpha-(2,4-Difluorophenyl)-5-fluoro-beta-methyl-alpha-(1H-1,2,4-triazol-1-ylmethyl)-4-pyrimidineethanol ; 4-Pyrimidineethanol, alpha-(2,4-difluorophenyl)-5-fluoro-beta-methyl-alpha-(1H-1,2,4-triazol-1-ylmethyl)-,(alphaR,betaS)- ; DRG-0301 ; UK-109,496 ; UNII-JFU09I87TR ; VRC ; Vfend ; Voriconazole ; (R-(R*,S*))-alpha-(2,4-difluorophenyl)-5-fluoro-beta-methyl-alpha-(1H-1,2,4-triazol-1-ylmethyl)-4-pyrimidineethanol ; 4-Pyrimidineethanol, alpha-(2,4-difluorophenyl)-5-fluoro-beta-methyl-alpha-(1H-1,2,4-triazol-1-ylmethyl)-, (R-(R*,S*))- . It is a cyrstalline solid.

Product Name

Voriconazole

Synthetic route

Voriconazole Chemical Properties

Voriconazole History

Voriconazole Uses

Voriconazole Toxicity Data With Reference

Voriconazole Safety Profile

Voriconazole Specification

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