2-Fluoro-6-methoxybenzonitrile Chemical Properties

Melting point:

103-105 °C(lit.)

Boiling point:

232.1±20.0 °C(Predicted)

Density 

1.18±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

color 

White to Almost white

BRN 

4179192

InChI

InChI=1S/C8H6FNO/c1-11-8-4-2-3-7(9)6(8)5-10/h2-4H,1H3

InChIKey

YPMSIWYNTPSPMV-UHFFFAOYSA-N

SMILES

C(#N)C1=C(OC)C=CC=C1F

CAS DataBase Reference

94088-46-7(CAS DataBase Reference)

NIST Chemistry Reference

Benzonitrile, 2-fluoro-6-methoxy-(94088-46-7)

Safety Information

Hazard Codes 

Xi,T,Xn

Risk Statements 

36/37/38-20/21/22

Safety Statements 

26-36

RIDADR 

3276

WGK Germany 

3

Hazard Note 

Toxic

HazardClass 

6.1

PackingGroup 

III

HS Code 

2926907090

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

2-Fluoro-6-methoxybenzonitrile Usage And Synthesis

Chemical Properties

White crystals

General Description

2-Fluoro-6-methoxybenzonitrile (FMBN) is a fluorinated organic building block used in organic synthesis. Molecular structure and vibrational spectra of FMBN have been investigated.

Synthesis

Synthetic route 2.1.5: 2-fluoro-6-methoxybenzonitrile (similar to WO 99/14187): 640.5 g (4.6 mol) of 2,6-difluorobenzonitrile was dissolved in 3.5 L of methanol and subsequently cooled to 0-5 °C. In this temperature range, 828.8 g of 30% sodium methanol solution was slowly added dropwise. After the dropwise addition, the reaction mixture was stirred at room temperature overnight. After completion of the reaction, the mixture was poured into 20 L of water and the precipitate was collected by filtration. The precipitate was washed sequentially twice with water and twice with heptane. The resulting solid was dried under vacuum at 50 °C. A final 740 g of white solid product was obtained in 99% yield of the theoretical value. The product was analyzed by GC and 1H NMR (CDCl3 as solvent) and the purity of the product was >95%.1H NMR data were as follows: δ = 3.95 ppm (single peak, 3H, O-CH3), 6.85 ppm (multiple peaks, 2H, aromatic H), 7.5 ppm (quadruple peak, 1H, aromatic H).

References

[1] Patent: WO2006/56433, 2006, A2. Location in patent: Page/Page column 29
[2] Journal of Heterocyclic Chemistry, 1988, vol. 25, p. 1173 - 1177
[3] Patent: WO2007/93530, 2007, A1. Location in patent: Page/Page column 244
[4] Journal of Medicinal Chemistry, 2012, vol. 55, # 7, p. 3135 - 3143
[5] Patent: WO2017/221092, 2017, A1. Location in patent: Paragraph 00153

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