5-Bromo-1,3-phenylenediamine Chemical Properties

Melting point:

92 °C

Boiling point:

336.1±22.0 °C(Predicted)

Density 

1.697±0.06 g/cm3(Predicted)

storage temp. 

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

form 

solid

pka

3.81±0.10(Predicted)

color 

Brown

Safety Information

HS Code 

2921511990

5-Bromo-1,3-phenylenediamine Usage And Synthesis

Synthesis

General procedure for the synthesis of 5-bromo-1,3-benzenediamine from 3,5-dinitrobromobenzene: To a methanol:water (V/V: 50 mL/50 mL) solution of 1-bromo-3,5-dinitrobenzene (10 g, 40 mmol) was added ammonium chloride (17.33 g, 323.9 mmol) and iron powder (11.31 g, 202.5 mmol). The reaction mixture was stirred and refluxed at 95 °C overnight. Upon completion of the reaction, it was filtered through a diatomaceous earth pad to remove the iron powder and the filtrate was concentrated by rotary evaporation to remove methanol. The remaining aqueous phase was extracted with dichloromethane (3 x 50 mL), the organic layers were combined, washed sequentially with water and saturated saline, and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography using appropriate eluents to afford 5-bromo-1,3-benzenediamine (7.01 g, 92% yield) as a yellow solid. The structure of the product was confirmed by 1H NMR (400 MHz, CDCl3): δ 6.25 (d, 2H, J=2.0 Hz), 5.90 (t, 1H, J=2.0 Hz), 3.60 (s, 4H).

References

[1] European Journal of Medicinal Chemistry, 2017, vol. 126, p. 1107 - 1117
[2] Patent: WO2011/75515, 2011, A1. Location in patent: Page/Page column 259-260
[3] Mendeleev Communications, 2015, vol. 25, # 6, p. 443 - 445
[4] Patent: WO2018/18091, 2018, A1. Location in patent: Paragraph 00125-00126

5-Bromo-1,3-phenylenediamine(33786-90-2)Related Product Information

• DIMETHYL 5-BROMOISOPHTHALATE
• 5-BROMOISOPHTHALALDEHYDE
• DIETHYL 5-BROMOISOPHTHALATE
• 5-Bromo-1,3-benzenediol
• 5-BROMOISOPHTHALIC ACID
• 1-BROMO-3,5-DINITRO-BENZENE
• 2-Bromo-4,6-dinitroaniline
• 5-Bromo-1,3-phenylenediamine
• 4-Chlorophenethylamine
• Disperse Blue 79
• 5-BROMO-2-METHYL-1,3-DINITROBENZENE
• Disperse Blue 291
• 4-BROMO-2,6-DINITROBENZOIC ACID
• Disperse Blue 94
• 1-BROMO-2-METHYL-3,5-DINITROBENZENE
• 2-BROMO-4,6-DINITROBENZOIC ACID
• 5-AMINO1-BROMO-2-METHYL-3-NITROBENZENE
• 4-BROMO-2,6-DINITROPHENYL ACETALDEHYDE