1,2-BIS(BROMOMETHYL)-4-NITROBENZENE Chemical Properties

Melting point:

68-72 °C

Boiling point:

384.6±32.0 °C(Predicted)

Density 

1.927±0.06 g/cm3(Predicted)

storage temp. 

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

Appearance

Light yellow to light brown Solid

1,2-BIS(BROMOMETHYL)-4-NITROBENZENE Usage And Synthesis

Synthesis

General procedure for the synthesis of 1,2-bis(bromomethyl)-4-nitrobenzene from 1,2-bis(bromomethyl)benzene: KNO3 (33.0 g, 330 mmol) was added in batches to a stirred solution of 1,2-bis(bromomethyl)benzene (72.2 g, 300 mmol) dissolved in CH2SO4 (600 mL) at 0 °C, and the addition process lasted for 1 hour. After the addition was completed, the reaction mixture continued to be stirred at 0 °C for 3 hours. Subsequently, the reaction mixture was poured into ice water and stirred at 0 °C for 2 hours. The solid product was collected by filtration, washed with water several times and dried to afford 1,2-bis(bromomethyl)-4-nitrobenzene (63.1 g, 68% yield) as a white solid with a melting point of 73-74 °C (EtOAc/petroleum ether). The structure of the product was confirmed by 1H NMR and 13C NMR: 1H NMR (δ, ppm): 8.25 (d, J = 2.3 Hz, 1H, H-3), 8.15 (dd, J = 8.4, 2.3 Hz, 1H, H-5), 7.56 (d, J = 8.4 Hz, 1H, H-6), 4.67 (s, 2H, CH2Br), 4.66 (s, 2H, CH2Br); 13C NMR (δ, ppm): 148.0, 143.4, 138.3, 132.1, 125.9, 124.1, 28.0, 27.5 Elemental analyses are consistent with calculated values for C8H7NBr2O2: C, 31.1%; H, 2.3%; N, 4.5%. Measured values: C, 31.1%; H, 2.3%; N, 4.5%.

References

[1] Journal of Medicinal Chemistry, 2008, vol. 51, # 21, p. 6853 - 6865
[2] Patent: WO2006/104406, 2006, A1. Location in patent: Page/Page column 109
[3] Patent: WO2016/90079, 2016, A1. Location in patent: Paragraph 00475-00476
[4] Patent: WO2017/135897, 2017, A1. Location in patent: Page/Page column 39

1,2-BIS(BROMOMETHYL)-4-NITROBENZENE(6425-66-7)Related Product Information

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