3-Bromo-1,2-diaminobenzene Chemical Properties

Melting point:

125-126 °C

Boiling point:

127-128 °C

Density 

1.697±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,2-8°C

form 

solid

pka

3.09±0.10(Predicted)

color 

Light yellow to yellow

Safety Information

Risk Statements 

43

Safety Statements 

36/37

HS Code 

2921511990

3-Bromo-1,2-diaminobenzene Usage And Synthesis

Uses

3-Bromo-1,2-diaminobenzene is used in the preparation of isomeric bromo analogues of Benzo-1H-triazole as potential inhibitors of protein kinases.

Synthesis

General procedure for the synthesis of 3-bromo-1,2-diaminobenzene from 4-bromo-2,1,3-benzothiadiazole: 4-bromo-benzo[c][1,2,5]thiadiazole (10 g, 46.5 mmol) and NaBH4 (17.6 g, 465 mmol) were added to a 2000 mL single-necked flask followed by 900 mL of ethanol (EtOH). The reaction mixture was stirred at room temperature for 16 hours. After completion of the reaction, the solvent was removed using a rotary evaporator. Subsequently, the reaction mixture was extracted with chloroform (CHCl3). The organic layer was washed with saturated brine solution and then the organic layer was dried with anhydrous magnesium sulfate (MgSO4). Finally, the solvent was removed by rotary evaporator to afford 3-bromo-1,2-diaminobenzene (8.0 g, 47.6 mmol, 92% yield).

References

[1] Patent: KR101612903, 2016, B1. Location in patent: Paragraph 0110-0112
[2] Journal of Physical Chemistry B, 2012, vol. 116, # 24, p. 7259 - 7268
[3] Patent: WO2009/111260, 2009, A1. Location in patent: Page/Page column 31-32
[4] Patent: WO2009/108838, 2009, A1. Location in patent: Page/Page column 95-96
[5] Chemical Communications, 2013, vol. 49, # 39, p. 4304 - 4306

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• ZERENEX E/6026596