4-(1H-BENZOIMIDAZOL-2-YL)-PHENYLAMINE Chemical Properties

Melting point:

248.0 to 252.0 °C

Boiling point:

466.3±47.0 °C(Predicted)

Density 

1.286±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

11.77±0.10(Predicted)

color 

White to Light yellow to Light orange

λmax

314nm(HCl aq.)(lit.)

Safety Information

Hazard Codes 

Xi

HS Code 

2933.99.8290

HazardClass 

IRRITANT

4-(1H-BENZOIMIDAZOL-2-YL)-PHENYLAMINE Usage And Synthesis

Synthesis Reference(s)

Journal of Medicinal Chemistry, 39, p. 3375, 1996 DOI: 10.1021/jm9600959

Synthesis

The reaction was carried out with 4-aminobenzoic acid (5 g, 5.78 mmol) and o-phenylenediamine (3.9 g, 3.68 mmol) in polyphosphoric acid (12.5 g) with stirring at 200 °C for 5 hours. Upon completion of the reaction, the mixture was cooled to room temperature and slowly poured into crushed ice. Subsequently, the precipitate was stirred in cold water. The pH was adjusted with ammonium hydroxide solution to 7. The solid product was collected by filtration and washed several times with methanol. Finally, the target compound 4-(1H-benzimidazol-2-yl)aniline (5) was purified as a white solid by silica gel column chromatography using ethyl acetate: hexane (4:1) as eluent. Yield: 82%; Melting point: 207-209 °C; 1H NMR (400 MHz, DMSO-d6): δ= 7.96 (d, 2H, J = 8.72 Hz, ArH), 7.55-7.51 (m, 2H, ArH), 7.16-7.14 (m, 2H, ArH), 6.75 (d, 2H, J = 8.24 Hz, ArH) , 4.45 (bs, 2H, NH2); 13C NMR (100 MHz, DMSO-d6): δ= 152.2,148.4,127.5,120.9,118.6,113.8 (ArC); MS (ESI), m/z: 210.2 (M++1).

References

[1] Chemical and Pharmaceutical Bulletin, 2007, vol. 55, # 1, p. 115 - 117
[2] Chinese Chemical Letters, 2011, vol. 22, # 3, p. 296 - 299
[3] European Journal of Medicinal Chemistry, 2017, vol. 126, p. 24 - 35
[4] European Journal of Medicinal Chemistry, 2016, vol. 117, p. 59 - 69
[5] Journal of the Chilean Chemical Society, 2012, vol. 57, # 2, p. 1122 - 1125,4

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