4-(1H-1,2,4-Triazol-1-ylmethyl)aniline Chemical Properties

Melting point:

124 °C

Boiling point:

402.1±47.0 °C(Predicted)

Density 

1.26±0.1 g/cm3(Predicted)

storage temp. 

-20°C Freezer

solubility 

Chloroform (Slightly), Methanol (Slightly)

pka

4.42±0.10(Predicted)

form 

Powder

color 

White to pale yellow

InChI

InChI=1S/C9H10N4/c10-9-3-1-8(2-4-9)5-13-7-11-6-12-13/h1-4,6-7H,5,10H2

InChIKey

ZGLQVRIVLWGDNA-UHFFFAOYSA-N

SMILES

C1(N)=CC=C(CN2C=NC=N2)C=C1

CAS DataBase Reference

119192-10-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

20/21/22-36/37/38-41-37/38

Safety Statements 

22-26-36/37/39

HazardClass 

6.1

HazardClass 

IRRITANT

HS Code 

2933998090

4-(1H-1,2,4-Triazol-1-ylmethyl)aniline Usage And Synthesis

Chemical Properties

Brown Solid

Uses

Rizatriptan intermediate

Uses

4-(1H-1,2,4-Triazol-1-ylmethyl)benzenamine is an intermediate useful in organic synthesis and other chemical processes.

Synthesis

General procedure for the synthesis of 4-[1H-1,2,4-triazol-1-ylmethyl]aniline from 1-(4-nitrophenyl)methyl-1,2,4-triazole: 1-(4-nitrophenyl)methyl-1,2,4-triazole (10.0 g, 49 mmol) was dissolved in a mixed solvent of ethanol (50 ml) and ethyl acetate (50 ml), 5N HCl (10 ml) and water (1 g). The hydrogenation reaction was carried out in a Parr hydrogenation unit at 40 psi hydrogen pressure using 10% Pd/C catalyst (1.0 g) until the hydrogen uptake reached 188 psi (about 10 min). Upon completion of the reaction, the catalyst was removed by Hyflo filtration and the solvent was removed by concentration under vacuum. The residue was azeotroped twice with ethanol to afford the target product 1-(4-aminophenyl)methyl-1,2,4-triazole hydrochloride (10.6 g, 100%). The product was confirmed by NMR hydrogen spectrum (360 MHz, D2O): δ 5.53 (2H, s, CH2), 7.37-7.48 (4H, m, Ar-H), 8.12 (1H, s, Ar-H), 8.66 (1H, s, Ar-H).

References

[1] Patent: US5567726, 1996, A
[2] Patent: US5298520, 1994, A
[3] Farmaco, 1989, vol. 44, # 9, p. 831 - 841
[4] European Journal of Medicinal Chemistry, 1989, vol. 24, # 5, p. 537 - 540
[5] Patent: US5567819, 1996, A

4-(1H-1,2,4-Triazol-1-ylmethyl)aniline(119192-10-8)Related Product Information

• N,N-Dimethylaniline
• ANILINE BLACK
• 3,3',5,5'-Tetramethylbenzidine dihydrochloride
• Tolyltriazole
• N,N-Dimethyl-1,4-phenylenediamine
• Aniline
• o-Toluidine
• N-Methylaniline
• 4-(1H-1,2,4-Triazol-1-ylmethyl)benzenamine hydrochloride
• 1-[(4-Hydrazinophenyl)methyl]-1H-1,2,4-triazole hydrochloride
• 1-(4-Nitrophenyl)methyl-1,2,4-triazole
• Rizatriptan
• 1,2,4-Triazole
• 1,2,3-1H-Triazole
• 1-(4-HYDRAZINOBENZYL)-1H-1,2,4-TRIAZOLE
• 2-(1H-1,2,4-TRIAZOL-1-YLMETHYL)ANILINE
• 3-(1H-1,2,4-TRIAZOL-1-YLMETHYL)ANILINE
• 4-(1H-1,2,4-Triazol-1-ylmethyl)aniline