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Name Voriconazole
EINECS629-701-5
CAS No. 137234-62-9
Density1.42 g/cm³
PSA76.72000
LogP2.17690
SolubilityN/A
Melting Point127-130 °C
FormulaC₁₆H₁₄F₃N₅O
Boiling Point508.6 °C at 760 mmHg
Molecular Weight349.315
Flash Point261.4 °C
Transport InformationN/A
Appearancecyrstalline solid
Safety26-36
Risk Codes22-36/38
Molecular Structure
Hazard SymbolsXn
SynonymsXn
Article Data35

Voriconazole 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%

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.

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Product Name

Voriconazole

Voriconazole Synthetic route

Voriconazole Chemical Properties

Voriconazole History

Voriconazole Uses

Voriconazole Toxicity Data With Reference

Voriconazole Safety Profile

Voriconazole Specification

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