4-PYRAZOL-1-YL-BENZONITRILE

4-PYRAZOL-1-YL-BENZONITRILE Property

Melting point:

89 °C

Boiling point:

316.5±25.0 °C(Predicted)

Density 

1.13±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

-0.63±0.10(Predicted)

color 

White to Light yellow

InChI

InChI=1S/C10H7N3/c11-8-9-2-4-10(5-3-9)13-7-1-6-12-13/h1-7H

InChIKey

SLPWCEHHSRUSKN-UHFFFAOYSA-N

SMILES

C(#N)C1=CC=C(N2C=CC=N2)C=C1

Safety

Hazard Codes 

Xi

RIDADR 

UN3439

HazardClass 

6.1

PackingGroup 

III

HS Code 

2933199090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

P501Dispose of contents/container to..…

4-PYRAZOL-1-YL-BENZONITRILE Chemical Properties,Usage,Production

Synthesis

The general procedure for the synthesis of 4-(1-pyrazolyl)benzonitrile from pyrazole and p-fluorobenzonitrile was as follows: 4-fluorobenzonitrile (204.2 g, 1.0 eq.), pyrazole (138.6 g, 1.22 eq.), and potassium carbonate (281.5 g, 1.22 eq.) were dissolved in DMF (1110 mL), and heated to a temperature of 120°C for 7 hours. After completion of the reaction, the suspension was cooled to 25 °C and diluted with water (2920 mL). The reaction mixture was extracted with methyl tert-butyl ether (MTBE, 3 x 1460 mL), and the organic phases were combined and washed sequentially with water (3 x 1460 mL) and saturated aqueous sodium chloride solution (1460 mL). The organic phase was concentrated at atmospheric pressure until the tank temperature rose to 65 °C, then heptane (1700 mL) was added over 30 min at 60-65 °C and distillation was continued to collect 300 mL of distillate. The solution was stirred at 60-65°C for 15 minutes and subsequently cooled to <5°C. The resulting slurry was filtered, the solid was washed with heptane (2 x 200 mL) and dried under vacuum to constant weight to afford the target product 4-(1-pyrazolyl)benzonitrile as a white solid (245.3 g, 87% yield). The product was characterized by 1H NMR (400 MHz, CDCl3): δ 6.51 (q, 1H), 7.71 (d, 2H), 7.75 (d, 1H), 7.81 (d, 2H), 7.98 (d, 1H).

References

[1] Patent: WO2009/61271, 2009, A1. Location in patent: Page/Page column 45-46
[2] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 11, p. 2955 - 2959
[3] Patent: US2011/224229, 2011, A1. Location in patent: Page/Page column 19
[4] Patent: WO2017/87837, 2017, A1. Location in patent: Paragraph 00269
[5] Patent: US9301951, 2016, B2. Location in patent: Page/Page column 231