4-FLUOROBENZOYLACETONITRILE Chemical Properties

Melting point:

84-88 °C

Boiling point:

311.9±22.0 °C(Predicted)

Density 

1?+-.0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Soluble in dimethylformamide, dimethyl sulfoxide.

pka

7.67±0.10(Predicted)

form 

Solid

color 

Yellow

λmax

247nm(EtOH)(lit.)

InChI

InChI=1S/C9H6FNO/c10-8-3-1-7(2-4-8)9(12)5-6-11/h1-4H,5H2

InChIKey

LOJBBLDAJBJVBZ-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

4640-67-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-22

Safety Statements 

26-36/37/39

WGK Germany 

3

Hazard Note 

Irritant

HazardClass 

6.1

HS Code 

29269090

4-FLUOROBENZOYLACETONITRILE Usage And Synthesis

Chemical Properties

White to light brown solid

Uses

4-Fluorobenzoylacetonitrile is used as a reagent in the synthesis of Blonanserin (B595850); a 5-HT2 serotonin receptor and D2 dopamine receptor antagonist, used as an antipsychotic. 4-Fluorobenzoylacetonitrile is also used in the preparation of pyrazolopyrimidines as potential antimicrobial and antioxidant agents.

Synthesis

The general procedure for the synthesis of 4-fluorobenzoylacetonitrile from methyl 4-fluorobenzoate and acetonitrile was as follows: methyl 4-fluorobenzoate (29.44 kg), toluene (177 L), and acetonitrile (59 L; 5.9 mole equivalents relative to methyl 4-fluorobenzoate) were added to a reactor. The reaction mixture was cooled to -5 to 0°C. A solution of sodium bis(trimethylmethylsilyl)amide (NaHMDS, 40% in THF) (192 L; 2 molar equivalents relative to methyl 4-fluorobenzoate) was slowly added while maintaining the temperature between -5 and +5 °C. The addition line was flushed with toluene (9 L) to ensure complete transfer. The reaction mixture was quenched by the addition of dilute hydrochloric acid while maintaining a temperature between -5 and +25°C. Continue to add acid until the pH falls below 5. Separate the layers and discard the lower aqueous layer. A small amount of solvent was removed by vacuum distillation. Toluene (59 L) was added and the mixture was heated to 85 to 90 °C to obtain a homogeneous solution. The mixture was cooled to 50 to 55 °C and n-heptane (29 L) was added to induce precipitation. The mixture was further cooled to 20 to 25 °C and the solid product was isolated by filtration and washed with n-heptane (59L). The wet product was dried under vacuum at 40 to 45°C to give 4-fluorobenzoylacetonitrile (26 kg, 83% yield) with 98.7% GC purity. The main impurity, 4-methoxybenzoylacetonitrile, was present in 0.03% (% GC area).

References

[1] Patent: JP2018/43989, 2018, A. Location in patent: Paragraph 0124-0131

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