3,5-Difluorobenzonitrile Chemical Properties

Melting point:

84-86 °C(lit.)

Boiling point:

160 °C

Density 

1.2490 (estimate)

storage temp. 

Sealed in dry,Room Temperature

Water Solubility 

Insoluble in water

form 

powder to crystal

color 

White to Almost white

BRN 

2082206

InChI

InChI=1S/C7H3F2N/c8-6-1-5(4-10)2-7(9)3-6/h1-3H

InChIKey

CQXZSEXZQVKCHW-UHFFFAOYSA-N

SMILES

C(#N)C1=CC(F)=CC(F)=C1

CAS DataBase Reference

64248-63-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-36-36/37/39-36/37

RIDADR 

3276

WGK Germany 

3

Hazard Note 

Harmful/Irritant

HazardClass 

6.1

PackingGroup 

III

HS Code 

29269090

MSDS

• Language:English Provider:3,5-Difluorobenzonitrile
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

3,5-Difluorobenzonitrile Usage And Synthesis

Uses

3,5-Difluorobenzonitrile is an aromatic nitrile compound. Aromatic nitrile compounds have a wide range of applications, serving not only as important chemical intermediates but also as key components in certain dyes, pesticides, and pharmaceuticals. 3,5-Difluorobenzonitrile can be synthesized from arylboronic acid.

Chemical Properties

white crystals

Synthesis Reference(s)

Journal of Medicinal Chemistry, 30, p. 486, 1987 DOI: 10.1021/jm00386a008

General Description

The vibrational wavenumbers, geometry and various thermodynamic parameters were studied for 3,5-difluorobenzonitrile.

Synthesis

General procedure for the synthesis of 3,5-difluorobenzonitrile from 3,5-difluorobromobenzene: iPrMgCl (2M in THF, 4.1 mL) and THF (5 mL) were added to a flask containing dry LiCl (0.35 g, 8.24 mmol) at 15 °C. After stirring for 15 min, a solution of 3,5-difluorobromobenzene (1.46 g, 8.03 mmol) in THF (1 mL) was slowly added to the reaction mixture and stirring was continued for 15 min. Subsequently, DMF (1.3 mL, 12 mmol) was added at 0 °C and the mixture was stirred for 2 hours. After completion of the reaction, aqueous NH3 (7 mL, 28-30%) and I2 (4.06 g, 16 mmol) were added to the mixture. After stirring at room temperature for 2 h, the reaction mixture was poured into saturated aqueous Na2SO3 solution and extracted with CHCl3 (3 x 30 mL). The organic layers were combined, dried with Na2SO4 and filtered. After removing the solvent under reduced pressure, the residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate = 9:1, v/v) to afford pure 3,5-difluorobenzonitrile (0.73 g) in 71% yield. Most of the nitrile compounds involved in this study were commercially available and were identified by comparison with real samples.

References

[1] Tetrahedron, 2013, vol. 69, # 5, p. 1462 - 1469

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