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137234-62-9

Basic Information
CAS No.: 137234-62-9
Name: Voriconazole
Article Data: 35
Cas Database
Molecular Structure:
Molecular Structure of 137234-62-9 (Voriconazole)
Formula: C16H14F3N5O
Molecular Weight: 349.315
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;
EINECS: 629-701-5
Density: 1.42 g/cm3
Melting Point: 127-130 °C
Boiling Point: 508.6 °C at 760 mmHg
Flash Point: 261.4 °C
Appearance: cyrstalline solid
Hazard Symbols: HarmfulXn
Risk Codes: 22-36/38
Safety: 26-36
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
ConditionsYield
With sodium hydrogencarbonate In dichloromethane for 0.5h;92%
With sodium hydrogencarbonate In water; ethyl acetate90.47%
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
ConditionsYield
With sodium hydroxide In dichloromethane; water pH=11 - 12;92%

voriconazole L-camphorsulfate

137234-62-9

voriconazole

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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%
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Chemistry

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

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.

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.

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.

Safety Profile

Safty information about Voriconazole (CAS NO.137234-62-9) is:
Hazard Codes: HarmfulXn
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.

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.