5-AMINOBENZOTRIAZOLE Chemical Properties

Melting point:

152-154°C

Boiling point:

479.4±18.0 °C(Predicted)

Density 

1.480±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

crystalline powder

pka

9.61±0.40(Predicted)

color 

Light beige/light brown

Water Solubility 

Insoluble in water.

BRN 

121262

CAS DataBase Reference

3325-11-9

EPA Substance Registry System

1H-Benzotriazol-5-amine (3325-11-9)

Safety Information

Hazard Codes 

Xi

Risk Statements 

20/21/22-36/37/38

Safety Statements 

22-36/37-26

RIDADR 

1325

TSCA 

Yes

HazardClass 

IRRITANT

PackingGroup 

III

HS Code 

2933998090

MSDS

• Language:English Provider:ALFA

5-AMINOBENZOTRIAZOLE Usage And Synthesis

Uses

5-Amino-1H-benzotriazole is used as azole building block.

Synthesis

General procedure for the synthesis of 1H-benzo[d][1,2,3]triazol-5-amine from 5-nitrobenzotriazole: a mixture of 5-nitrobenzotriazole (10 mmol) and SnCl2-2H2O (50 mmol) in EtOAc (50 mL) was refluxed for 12 hours. The progress of the reaction was monitored by TLC and after confirming the completion of the reaction, the reaction mixture was cooled to room temperature. Subsequently, the pH of the reaction mixture was adjusted to 8-9 with saturated aqueous NaHCO3. The reaction mixture was extracted with EtOAc (2 × 150 mL) and the organic phases were combined. The organic phase was washed with brine (200 mL), dried over anhydrous Na2SO4, concentrated and purified by silica gel column chromatography (200-300 mesh) to afford 1H-benzo[d][1,2,3]triazol-5-amine. Yield: 90% as an orange solid, Melting point: 157-159°C (literature value not reported); IR (KBr, cm-1): 3375, 3077, 1630, 1521, 1430, 1320, 885, 842, 739; 1H NMR (500 MHz, DMSO-d6) δ: 7.65 (d, J = 8.5 Hz, 1H) , 6.73 (d, J = 8.0 Hz, 1H), 6.61 (s, 1H); HRMS (ESI): C6H7N4 ([M + H]+) Calculated value: 135.0665, measured value: 135.0665.

References

[1] Farmaco, 1989, vol. 44, # 6, p. 609 - 618
[2] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 2, p. 181 - 187
[3] Collection of Czechoslovak Chemical Communications, 1992, vol. 57, # 3, p. 531 - 539

5-AMINOBENZOTRIAZOLE(3325-11-9)Related Product Information

• 5-AMINOBENZOTRIAZOLE
• 5-NITROBENZOTRIAZOLE
• 5-AMINOBENZOTRIAZOLE
• 1-AMINOBENZOTRIAZOLE,1-Aminobenzotriazole 97%
• BOC-THIONOLEU-1-(6-NITRO)BENZOTRIAZOLIDE
• 2-PHENYL-2H-BENZOTRIAZOL-5-YLAMINE
• 2-(4-METHOXY-PHENYL)-2H-BENZOTRIAZOL-5-YLAMINE
• 2-AMINOBENZOTRIAZOLE
• N-(α-Methylbenzyl)-1-aminobenzotriazole,n-benzyl-1-aminobenzotriazol
• N-alpha-ethylbenzyl-1-aminobenzotriazole
• 1-HYDROXY-5-NITRO-1,2,3-BENZOTRIAZOLE
• 6-NITRO-1H-BENZOTRIAZOLE-4-CARBOXYLIC ACID
• 6-METHYL-2-PHENYL-2H-BENZOTRIAZOL-5-YLAMINE
• 5-AMINOBENZOTRIAZOLE DIHYDROCHLORIDE
• AKOS BB-9424
• 5,7-DIBROMO-4,6-DINITRO-1H-1,2,3-BENZOTRIAZOLE
• 5-AMINO-2-(P-TOLYL)-2H-BENZOTRIAZOLE
• 2-(4-ETHOXY-PHENYL)-2H-BENZOTRIAZOL-5-YLAMINE