1480-96-2

Basic information

• Product Name: 2-Methoxy-5-fluorouracil
• Synonyms: 5-FLUORO-2-METHOXY-4(1H)PYRIMIDINONE, 9&;5-Fluoro-2-methoxy-pyrimidin-4-ol;4(1H)-Pyrimidinone, 5-fluoro-2-methoxy- (9CI);2-Methoxyl-5-fluorouracil;2-O-METHYL-5-FLUOROURACIL;5-Fluoro-2-methoxy-4(3H)-pyrimidinone;2-Methoxy-5-fluorouracil;5-fluoro-2-methoxy-1H-pyrimidin-6-one
• CAS NO: 1480-96-2
• Molecular Formula: C₅H₅FN₂O₂
• Molecular Weight: 144.1
• EINECS: 473-810-9
• Product Categories: PYRIMIDINE;Pyridines, Pyrimidines, Purines and Pteredines;INTERMEDIATESOFFINASTERIDE;Heterocyclic Compounds;Bases & Related Reagents;Heterocycles;Nucleotides;Building Blocks;Heterocyclic Building Blocks;Pyrimidines
• Mol File: 1480-96-2.mol
• Article Data: 2

Chemical Properties

• Melting Point: 204-208 °C(lit.)
• Boiling Point: 225.1℃[at 101 325 Pa]
• Appearance: /
• Density: 1.44 g/cm³
• Vapor Pressure: 0.001Pa at 25℃
• Refractive Index: 1.536
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 6.34±0.50(Predicted)
• Water Solubility: 5.49g/L at 20℃
• CAS DataBase Reference: 2-Methoxy-5-fluorouracil(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methoxy-5-fluorouracil(1480-96-2)
• EPA Substance Registry System: 2-Methoxy-5-fluorouracil(1480-96-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 1480-96-2(Hazardous Substances Data)

Usage

Description

2-Methoxy-5-fluorouracil, also known as 5-Fluoro-4-hydroxy-2-methoxypyrimidine (CAS# 1480-96-2), is an organic compound with off-white solid properties. It is primarily used in the field of organic synthesis due to its unique chemical structure and reactivity.

Uses

Used in Organic Synthesis:
2-Methoxy-5-fluorouracil is used as a synthetic building block for the development of various chemical compounds. Its application in organic synthesis is attributed to its unique structure, which allows for further functionalization and the creation of a wide range of molecules with potential applications in different industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-Methoxy-5-fluorouracil is used as an intermediate in the synthesis of therapeutic agents, particularly those with potential anticancer properties. Its incorporation into drug molecules can enhance their efficacy and selectivity towards cancer cells, making it a valuable component in the development of novel cancer treatments.
Used in Research and Development:
2-Methoxy-5-fluorouracil is also utilized in research and development settings, where it serves as a key compound for studying the mechanisms of action, structure-activity relationships, and potential applications of various drug candidates. Its unique chemical properties make it an attractive candidate for exploring new avenues in drug discovery and development.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C5H5FN2O2/c1-10-5-7-2-3(6)4(9)8-5/h2H,1H3,(H,7,8,9)

Synthetic route

potassium-compound of 2-fluoro-3-oxo-propionic acid ethyl ester + O-methyl-uronium chloride → 2-methoxy-5-fluorouracil (1480-96-2)

ethanol (64-17-5) + sodium methylate (124-41-4) + o-methylisourea hydrochloride (5329-33-9) + potassium-compound of 2-fluoro-3-hydroxy-acrylic acid ethyl ester → 2-methoxy-5-fluorouracil (1480-96-2)

O-methylisourea hemisulphate + methyl fluoroacetate (453-18-9) + formic acid ethyl ester (109-94-4) → 2-methoxy-5-fluorouracil (1480-96-2)

Conditions	Yield
Stage #1: formic acid ethyl ester With sodium methylate In toluene at 10 - 20℃; Large scale; Stage #2: methyl fluoroacetate In toluene at 8 - 40℃; for 20h; Large scale; Stage #3: O-methylisourea hydrosulfate With sodium methylate In methanol at 40℃; for 6h; Large scale;

2-methoxy-5-fluorouracil (1480-96-2) → 2-methoxy-4-chloro-5-fluoropyrimidine (1801-06-5)

Conditions	Yield
With triethylamine; trichlorophosphate In toluene at 50 - 80℃;	95%
With N,N-dimethyl-aniline; trichlorophosphate at 110℃; for 1.5h;	34%

2-methoxy-5-fluorouracil (1480-96-2) → 5-fluorouracil (51-21-8)

Conditions	Yield
With hydrogenchloride In methanol at 28℃; for 5h; Temperature;	78.3%
With hydrogenchloride In water at 55℃; for 3h; Large scale;	65.24 kg

Upstream product

• 4330-22-7 5-fluoro-2,4-dimethoxypyrimidine 
• 24285-39-0 O-methylisourea hydrosulfate 
• 453-18-9 methyl fluoroacetate 
• 109-94-4 formic acid ethyl ester 
• 64-17-5 ethanol 
• 124-41-4 sodium methylate 
• 5329-33-9 o-methylisourea hydrochloride 

Downstream Products

• 51-21-8 5-fluorouracil 
• 1801-06-5 2-methoxy-4-chloro-5-fluoropyrimidine 

Relevant articles and documents

Composition of 5-fluorouracil and preparation method of composition

The invention discloses a refining method of 5-fluorouracil. The method comprises the following steps: dissolving 5-fluorouracil into an organic solvent, preferably DMSO (dimethyl sulfoxide), and performing heating and stirring till dissolution; naturally cooling filtrate till a crystal is separated; performing filtration, washing filter cakes by using a polar solvent, and performing pumping and vacuum drying. By adopting the novel refining method, the content of impurities in the 5-fluorouracil can be reduced to 0.01% or less, the product purity is 99.98% or greater, and the refining yield isgreater than 70%. In addition, the refining method disclosed by the invention is simple in process, convenient in operation, low in production cost, high in product purity, stable in process and applicable to industrial production.