| Identification | More | [Name]
4-(1H-IMIDAZOL-1-YL)BENZONITRILE | [CAS]
25372-03-6 | [Synonyms]
1-(4-CYANOPHENYL)IMIDAZOLE
4-(1H-IMIDAZOL-1-YL)BENZENECARBONITRILE
4-(1H-IMIDAZOL-1-YL)BENZONITRILE
4-(1-IMIDAZOLYL)BENZONITRILE
4-IMIDAZOL-1-YL-BENZONITRILE
BUTTPARK 96\50-66 | [Molecular Formula]
C10H7N3 | [MDL Number]
MFCD00127147 | [Molecular Weight]
169.18 | [MOL File]
25372-03-6.mol |
| Chemical Properties | Back Directory | [Appearance]
off-white crystalline powder | [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 Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S36/37:Wear suitable protective clothing and gloves . | [RIDADR ]
3276 | [HazardClass ]
IRRITANT | [PackingGroup ]
III | [HS Code ]
2933299090 |
| Hazard Information | Back Directory | [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 |
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