5-Fluoro-2-nitroanisole Chemical Properties

Melting point:

49-51°C

Boiling point:

272°C(lit.)

Density 

1.321±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

form 

powder to crystal

color 

White to Amber

InChI

InChI=1S/C7H6FNO3/c1-12-7-4-5(8)2-3-6(7)9(10)11/h2-4H,1H3

InChIKey

WLKUSVNHZXUEFO-UHFFFAOYSA-N

SMILES

C1([N+]([O-])=O)=CC=C(F)C=C1OC

CAS DataBase Reference

448-19-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22-52

HazardClass 

IRRITANT

HS Code 

2909309090

5-Fluoro-2-nitroanisole Usage And Synthesis

Uses

3-Fluoro-6-nitroanisole is a reagent used in the synthetic preparation of imidazopyridines as inhibitors of insulin-like growth factor-1 receptor.

Synthesis

In a 5L four-necked flask, 2500 g of N,N-dimethylformamide (DMF), 5-fluoro-2-nitrophenol (500 g, 3.20 mol) and anhydrous potassium carbonate (483 g, 3.50 mol) were added and the mixture was heated up to 60 °C. Dimethyl sulfate (424 g, 3.36 mol) was slowly added dropwise for a controlled period of 2-3 hours. After the dropwise addition, the reaction temperature was raised to 90-100 °C and the reaction was maintained for 5-6 hours. The reaction progress was monitored by gas chromatography (GC) until the content of 5-fluoro-2-nitrophenol was below 0.5%. The reaction mixture was cooled to 50 °C, at which point the monomethyl potassium sulfate salt precipitated. The filtrate was subjected to decompression distillation to recover DMF, resulting in 2-nitro-5-fluoroanisole (515 g, yellow oily liquid). The product was analyzed by GC with 99.5% purity and 94.1% yield.

References

[1] Chemical and Pharmaceutical Bulletin, 1991, vol. 39, # 9, p. 2323 - 2332
[2] Patent: CN106083536, 2016, A. Location in patent: Paragraph 0035; 0036
[3] Heterocycles, 1992, vol. 34, # 12, p. 2301 - 2311
[4] Patent: WO2010/71885, 2010, A1. Location in patent: Page/Page column 443
[5] Patent: WO2010/115688, 2010, A1. Location in patent: Page/Page column 146

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