2-BROMO-4-METHYL-6-NITROANILINE Chemical Properties

Melting point:

64-66

Boiling point:

329.1±37.0 °C(Predicted)

Density 

1.698±0.06 g/cm3(Predicted)

storage temp. 

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

pka

-1.74±0.25(Predicted)

Appearance

Light brown to orange Solid

InChI

InChI=1S/C7H7BrN2O2/c1-4-2-5(8)7(9)6(3-4)10(11)12/h2-3H,9H2,1H3

InChIKey

VFPKZASVVCBVMG-UHFFFAOYSA-N

SMILES

C1(N)=C([N+]([O-])=O)C=C(C)C=C1Br

CAS DataBase Reference

827-24-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

HazardClass 

IRRITANT

HS Code 

2921420090

2-BROMO-4-METHYL-6-NITROANILINE Usage And Synthesis

Synthesis

4-Methyl-2-nitroaniline (131.2 g, 862 mmol) was used as a raw material and suspended in glacial acetic acid (1.25 L). Bromine (54 mL, 1.05 mol) was added slowly over 1 h at ambient temperature. After addition, the reaction mixture was continued to be stirred for 1 hour. Subsequently, the reaction solution was poured into water (7.5 L) and the suspension was stirred for 30 minutes. The solid product was collected by filtration, washed thoroughly with water (5 x 1 L) and dried to give 2-bromo-4-methyl-6-nitroaniline (187.2 g, 94%) as an orange solid. Its 1H NMR (CDCl3) data were as follows: δ 7.94 (1H, s), 7.56 (1H, s), 6.47 (2H, br s), 2.27 (3H, s).

References

[1] Organic Letters, 2006, vol. 8, # 22, p. 4989 - 4992
[2] Chemistry - A European Journal, 2015, vol. 21, # 52, p. 18915 - 18920
[3] Journal of Labelled Compounds and Radiopharmaceuticals, 1995, vol. 36, # 3, p. 281 - 288
[4] Journal of Antibiotics, 1994, vol. 47, # 12, p. 1456 - 1465
[5] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 20, p. 6026 - 6032

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