5-AMINOBENZOTRIAZOLE

5-AMINOBENZOTRIAZOLE Property

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

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

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

5-AMINOBENZOTRIAZOLE Chemical Properties,Usage,Production

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