4-(1H-IMIDAZOL-1-YL)BENZONITRILE

4-(1H-IMIDAZOL-1-YL)BENZONITRILE Property

Melting point:

151-153 °C

Boiling point:

358.1±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

4.85±0.10(Predicted)

color 

White to Light yellow to Light orange

CAS DataBase Reference

25372-03-6(CAS DataBase Reference)

Safety

Hazard Codes 

Xn

Risk Statements 

20/21/22

Safety Statements 

36/37

RIDADR 

3276

HazardClass 

IRRITANT

PackingGroup 

III

HS Code 

2933299090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

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.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

P405Store locked up.

P501Dispose of contents/container to..…

4-(1H-IMIDAZOL-1-YL)BENZONITRILE Chemical Properties,Usage,Production

Chemical Properties

off-white crystalline powder

Uses

4-(1H-Imidazol-1-yl)benzonitrile is a nitroimidazoles with mutagenic properties. A useful research chemical.

Synthesis

Under nitrogen protection, 1500 mL of anhydrous dimethylformamide (DMF) was added to a 1000 mL four-necked flask, followed by 72.67 g (0.6 mol) of p-fluorobenzonitrile and 61.2 g (0.9 mol) of imidazole sequentially. Finally, 21.6 g (0.9 mol) of sodium hydride was slowly added. The reaction mixture was heated to 100 °C, kept at this temperature and stirred for 4 hours, followed by continued stirring at room temperature overnight. Upon completion of the reaction, the mixture was poured into water and extracted with dichloromethane several times. The organic phases were combined, dried over anhydrous sodium sulfate and concentrated on a rotary evaporator. Finally, the product was dried under reduced pressure at 60 °C to give 94 g of 4-(imidazol-1-yl)benzonitrile in 93% yield of the theoretical value. The product was characterized by 1H-NMR (400 MHz, CDCl3): δ= 7.27 (s, 1H); 7.35 (s, 1H); 7.54 (d, J = 8.8 Hz, 2H); 7.81 (d, J = 8.8 Hz, 2H); 7.95 (s, 1H).

References

[1] Synthetic Communications, 2008, vol. 38, # 4, p. 626 - 636
[2] Patent: WO2006/56418, 2006, A2. Location in patent: Page/Page column 57
[3] Patent: US2009/18330, 2009, A1. Location in patent: Page/Page column 14
[4] Advanced Synthesis and Catalysis, 2007, vol. 349, # 11-12, p. 1938 - 1942
[5] Monatshefte fur Chemie, 2004, vol. 135, # 4, p. 419 - 423