5-PHENYL-1H-IMIDAZOL-2-AMINE Chemical Properties

Melting point:

245 °C(Solv: ethanol (64-17-5))

Boiling point:

421.3±38.0 °C(Predicted)

Density 

1.238±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

14.75±0.10(Predicted)

Appearance

Yellow to brown Solid

InChI

InChI=1S/C9H9N3/c10-9-11-6-8(12-9)7-4-2-1-3-5-7/h1-6H,(H3,10,11,12)

InChIKey

NODFMZCEEBQXME-UHFFFAOYSA-N

SMILES

C1(N)NC(C2=CC=CC=C2)=CN=1

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36/38

Safety Statements 

26

WGK Germany 

3

5-PHENYL-1H-IMIDAZOL-2-AMINE Usage And Synthesis

Synthesis

Compound 17 (500 mg) was taken as raw material and mixed with 6M hydrochloric acid (2.2 mL) and methanol (2.5 mL) and reacted at reflux for 3 hours. After completion of the reaction, the mixture was cooled to room temperature and the precipitate was collected by filtration. The filtrate was concentrated under vacuum and the residue was dissolved in water and neutralized with 1 M sodium hydroxide solution. A precipitate was precipitated from the neutralized solution, collected by vacuum filtration and washed sequentially with water and ether to afford the target product 5-phenyl-1H-imidazol-2-amine (18, 131 mg, 33% yield) as a light brown solid. The product was characterized by 1H NMR (DMSO-d6): δ 5.25 (2H, s), 6.96 (1H, s), 7.07 (1H, t, J = 7.5 Hz), 7.26 (2H, t, J = 7.5 Hz), 7.57 (2H, d, J = 7.5 Hz), 10.53 (1H, br s). Mass spectrometry analysis showed FAB MS m/e (M + H)+ 160; high-resolution mass spectrometry (ESI) measured 160.0875 calculated and 160.0871 measured values for C9H10N3 (M + H)+. Elemental analyses of the calculated values (C9H9N3-3H2O): C, 65.68; H, 5.88; N, 25.53; measured values: C. 65.81; H, 5.49; N, 25.19.

References

[1] Journal of Medicinal Chemistry, 2018, vol. 61, # 7, p. 2806 - 2822
[2] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 13, p. 3873 - 3881
[3] Journal of Heterocyclic Chemistry, 2017, vol. 54, # 1, p. 524 - 530
[4] Journal of Heterocyclic Chemistry, 2018, vol. 55, # 6, p. 1410 - 1418

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