137234-88-9

Basic information

• Product Name: 4-Ethyl-5-fluoropyridine
• Synonyms: 4-ethyl-5-fluoropyridine;4-ETHYL-5-FLUOROPYRIMIDINE;4-ETHYL-5-FLUOROPYRI;Pyrimidine, 4-ethyl-5-fluoro- (9CI);Ubidearenone;4-Ethyl-5-fluoropyrimidin...;5-Fluoro-4-ethylpyriMidine;Voriconazole IMpurity C
• CAS NO: 137234-88-9
• Molecular Formula: C6H7FN2
• Molecular Weight: 126.13
• EINECS: 1308068-626-2
• Product Categories: PYRIMIDINE;Amines;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;Fluorine series
• Mol File: 137234-88-9.mol

Chemical Properties

• Boiling Point: 169.5 ºC at 760 mmHg
• Flash Point: 56.3 ºC
• Appearance: /
• Density: 1.117 g/cm³
• Vapor Pressure: 4.45mmHg at 25°C
• Refractive Index: 1.478
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 0.95±0.16(Predicted)
• Stability: Volatile
• CAS DataBase Reference: 4-Ethyl-5-fluoropyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Ethyl-5-fluoropyridine(137234-88-9)
• EPA Substance Registry System: 4-Ethyl-5-fluoropyridine(137234-88-9)

Safety Data

• Hazardous Substances Data: 137234-88-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Ethyl-5-fluoropyridine is used as an impurity in the production of Voriconazole (V760000), which is an antifungal medication. It plays a significant role in ensuring the quality and safety of the final drug product by being identified and controlled during the manufacturing process.
As a Voriconazole (V760000) impurity, 4-Ethyl-5-fluoropyrimidine (Voriconazole EP Impurity C) is essential for maintaining the purity and efficacy of the antifungal medication. The presence of this impurity is monitored and regulated to ensure that the therapeutic benefits of Voriconazole are not compromised, and the potential risks associated with impurities are minimized.

InChI:InChI=1/C7H8FN/c1-2-6-3-4-9-5-7(6)8/h3-5H,2H2,1H3

Upstream product

• 137234-85-6 2,4-dichloro-6-ethyl-5-fluoropyrimidine 

Downstream Products

• 137234-63-0 2-(2,4-difluorophenyl)-3-(5-fluoro-4-pyrimidinyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol 
• 137234-63-0 2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butane-2-ol 
• 137234-62-9 voriconazole 
• 188416-34-4 (2R,3S)-2-(2,4-difluorophenyl)-3-(5-fluoro-4-pyrimidinyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol (1R)-10-camphorsulfonate 

Relevant articles and documents

Process development of voriconazole: A novel broad-spectrum triazole antifungal agent

In the synthesis of (2R,3S)-2-(2,4-difluorophenyl)-3-(5-fluoro-4-pyrimidinyl)-1-(1H-1,2,4-triazol-1- yl)-2-butanol (voriconazole), the relative stereochemistry is set in the addition of a 4-(1-metalloethyl)-5-fluoropyrimidine derivative to 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)-1-ethanone. The diastereo-control of this reaction has been examined by variation of pyrimidine substitution pattern and by changes in the metalation and reaction conditions. Excellent diastereoselection (12: 1) is obtained using an organozinc derivative of 6-(1-bromoethyl)-4-chloro-5-fluoropyrimidine. After removal of the chlorine from the pyrimidine ring, the absolute stereochemistry of voriconazole is established via a diastereomeric salt resolution process using (1R)-10-camphorsulfonic acid. Synthetic routes to the pyrimidine partner have also been evaluated. The initial six-step development route from 5-fluorouracil has been superseded by a four-step synthesis involving fluorination of methyl 3-oxopentanoate and cyclisation with formamidine acetate.

Triazole antifungal agents

The invention provide antifungal compounds of the formula: STR1 and pharmaceutically acceptable salts thereof, wherein R is phenyl substituted by 1 to 3 substituents each independently selected from halo, --CF3 and --OCF3 ; R1 is C1 -C4 alkyl; R2 is H or C1 -C4 alkyl; X is CH or N; and Y is F or Cl.