5-PHENYL-1H-1,2,4-TRIAZOL-3-AMINE Chemical Properties

Melting point:

191-193℃

Boiling point:

276.07°C (rough estimate)

Density 

1.315±0.06 g/cm3 (20 ºC 760 Torr)

refractive index 

1.5872 (estimate)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

powder to crystal

pka

10.78±0.40(Predicted)

color 

Crystals from water

InChI

InChI=1S/C8H8N4/c9-8-10-7(11-12-8)6-4-2-1-3-5-6/h1-5H,(H3,9,10,11,12)

InChIKey

GHUDJFJZFUVPIQ-UHFFFAOYSA-N

SMILES

N1C(N)=NC(C2=CC=CC=C2)=N1

Safety Information

Hazard Codes 

Xi

HazardClass 

IRRITANT

HS Code 

2922390090

5-PHENYL-1H-1,2,4-TRIAZOL-3-AMINE Usage And Synthesis

Uses

5-Phenyl-4h-1,2,4-triazol-3-amine, is an intermediate in the synthesis of WP155. 5-Phenyl-4h-1,2,4-triazol-3-amine is also used in biological studies to evaluate its pharmacological activity as it can be applied to a method for reducing susceptibility to tumor formation induced by 3-deoxyglucosone and precursors thereof.

Safety Profile

Reaction with nitrous acid gives atouch sensitive explosive product. Upon decomposition itemits toxic fumes of NOx.

Synthesis

N-benzamidoguanidine (4.76 g, 26.7 mmol) was used as raw material and dissolved in 40 mL of water. The reaction mixture was heated to 110 °C and refluxed for 6 hours. After completion of the reaction, the solvent was removed by distillation under reduced pressure to afford the target product 3-phenyl-1H-1,2,4-triazol-5-amine (3.0 g, 18.7 mmol, 70.1% yield).

References

[1] Patent: JP6099045, 2017, B2. Location in patent: Paragraph 0064
[2] Journal of Medicinal Chemistry, 1996, vol. 39, # 15, p. 3019 - 3029
[3] Bioorganic Chemistry, 2013, vol. 50, p. 34 - 40
[4] European Journal of Medicinal Chemistry, 2016, vol. 113, p. 11 - 27
[5] European Journal of Medicinal Chemistry, 2018, vol. 156, p. 774 - 789

5-PHENYL-1H-1,2,4-TRIAZOL-3-AMINE(4922-98-9)Related Product Information

• 5-(2-Methylphenyl)-4H-1,2,4-triazol-3-amine
• 5-(2-Methoxyphenyl)-4H-1,2,4-triazol-3-amine
• TRIAMIPHOS
• 5-(4-Methylphenyl)-4H-1,2,4-triazol-3-amine
• 5-(4-Methoxyphenyl)-4H-1,2,4-triazol-3-amine
• 5-(3-Nitrophenyl)-4H-1,2,4-triazol-3-amine
• 5-(4-Nitrophenyl)-4H-1,2,4-triazol-3-amine
• 5-(4-(Trifluoromethyl)phenyl)-4H-1,2,4-triazol-3-amine
• 5-(3-(Trifluoromethyl)phenyl)-4H-1,2,4-triazol-3-amine
• 3-Amino-1,2,4-Triazole
• 5-METHYL-[1,2,4]TRIAZOLO[1,5-C]QUINAZOLIN-2-YLAMINE
• 5-(4-FLUOROPHENYL)-4H-1,2,4-TRIAZOL-3-AMINE
• 5-(2,4-DICHLORO-PHENYL)-4H-[1,2,4]TRIAZOL-3-YLAMINE
• 5-PHENYL-1H-1,2,4-TRIAZOL-3-AMINE
• N-PHENYL-1H-1,2,4-TRIAZOL-5-AMINE
• 3-(benzylsulfanyl)-5-phenyl-4H-1,2,4-triazol-4-amine
• 2-Phenyl-2H-1,2,3-triazol-4-amine
• 5-[3-(DIMETHYLAMINO)PHENYL]-4H-1,2,4-TRIAZOL-3-AMINE