1,2-BENZENEDIAMINE, 4-BROMO-N2-METHYL- Chemical Properties

Boiling point:

289℃

Density 

1.578

Flash point:

129℃

storage temp. 

2-8°C(protect from light)

pka

5.85±0.10(Predicted)

form 

viscous liquid

color 

Brown to balck

Safety Information

HS Code 

2921599090

1,2-BENZENEDIAMINE, 4-BROMO-N2-METHYL- Usage And Synthesis

Synthesis

The reaction of 5-bromo-N-methyl-2-nitroaniline (350 mg, 1.51 mmol) with zinc powder (495 mg, 7.57 mmol) and ammonium chloride (810 mg, 15.15 mmol) in a solvent mixture of methanol (4 mL) and water (2 mL) was stirred for 1 h at room temperature. Upon completion of the reaction, insoluble material was removed by filtration and the filtrate was neutralized with saturated sodium bicarbonate solution. Subsequently, the reaction mixture was concentrated and extracted with ethyl acetate. The organic layer was separated, washed sequentially with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to afford 4-bromo-2-methylaminobenzenamine as a brown solid (282 mg, 93% yield). The product was confirmed by 1H NMR (400 MHz, DMSO-d6): δ 2.68 (3H, d, J = 4.9 Hz), 4.60 (2H, s), 4.87 (1H, d, J = 4.9 Hz), 6.32-6.58 (3H, m). The mass spectrum (ESI/APCI) showed m/z = 202.09 [M + H]+.

References

[1] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 11, p. 2486 - 2503
[2] Patent: CN108689942, 2018, A. Location in patent: Paragraph 0463; 0468-0469
[3] Patent: WO2012/174312, 2012, A2. Location in patent: Page/Page column 216-217
[4] Patent: WO2008/82487, 2008, A2. Location in patent: Page/Page column 111-112
[5] Patent: WO2004/111036, 2004, A1. Location in patent: Page 21

1,2-BENZENEDIAMINE, 4-BROMO-N2-METHYL-(337915-79-4)Related Product Information

• (5-Bromo-2-nitro-phenyl)-methyl-amine
• 1H-Benzimidazole-1-carboxylic acid, 5-bromo-2,3-dihydro-3-methyl-2-oxo-, 1,1-dimethylethyl ester