3-Bromoindazole Chemical Properties

Melting point:

143-147 °C

Boiling point:

333.8±15.0 °C(Predicted)

Density 

1.770±0.06 g/cm3(Predicted)

storage temp. 

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

form 

solid

pka

11.82±0.40(Predicted)

Appearance

White to off-white Solid

CAS DataBase Reference

40598-94-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

T

Risk Statements 

25-36/37/38

Safety Statements 

26-45

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

3

HazardClass 

6.1

PackingGroup 

Ⅲ

HS Code 

29349990

3-Bromoindazole Usage And Synthesis

Chemical Properties

White solid

Uses

3-Bromoindazole was studied in its ability to inhibit blue light-mediated seedling development. Used to study the blue light mechanism and the genetic control of cryptochromes in the growth and development of plant species.

Synthesis

General procedure for the synthesis of 3-bromoindazole from indazole: 1H-indazole (3.00 g, 25.4 mmol) was suspended in 2.0 M sodium hydroxide solution (70 mL) at ambient temperature and a solution of bromine (3.00 g, 18.8 mmol) was slowly added. Subsequently, 2.0 M sodium hydroxide solution (30 mL) was added dropwise. The reaction mixture was stirred for 3 h. Sodium bisulfite (0.1 g) was added to quench the reaction, followed by acidification with the addition of 2.0 N hydrochloric acid solution (80 mL). The precipitate was collected by filtration and washed with water to give the final 3-bromoindazole (3.98 g, 80% yield). The product characterization data were as follows: melting point 136 °C; 1H NMR (CDCl3) δ 13.4 (broad single peak, 1H), 7.57 (multiple peaks, 2H), 7.45 (triple peak, 1H), 7.22 (triple peak, 1H); EI-MS (m/z) 198 [M+2]+, 196 [M]+.

References

[1] RSC Advances, 2016, vol. 6, # 93, p. 90031 - 90034
[2] Journal of Organic Chemistry, 2018, vol. 83, # 2, p. 930 - 938
[3] Organic Letters, 2015, vol. 17, # 4, p. 1042 - 1045
[4] Patent: US2002/103229, 2002, A1
[5] Patent: US2004/127536, 2004, A1

3-Bromoindazole(40598-94-5)Related Product Information

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