5-BROMO-4-NITRO-1H-IMIDAZOLE Chemical Properties

Melting point:

281-282℃ (DEC.)

Boiling point:

345 °C

Density 

2.156

storage temp. 

Sealed in dry,Room Temperature

pka

5.60±0.10(Predicted)

Appearance

White to off-white Solid

InChI

InChI=1S/C3H2BrN3O2/c4-2-3(7(8)9)6-1-5-2/h1H,(H,5,6)

InChIKey

KSEFBYAEHWXHLM-UHFFFAOYSA-N

SMILES

C1NC(Br)=C([N+]([O-])=O)N=1

Safety Information

HS Code 

2933299090

5-BROMO-4-NITRO-1H-IMIDAZOLE Usage And Synthesis

Synthesis

Example 312A Synthesis of 5-bromo-4-nitro-1H-imidazole: 4-bromo-1H-imidazole (2.0 g, 13.6 mmol) was mixed with concentrated nitric acid (0.947 mL, 14.96 mmol) in concentrated sulfuric acid (20 mL), and reacted for 1 hr at 110°C. After completion of the reaction, the mixture was cooled to 25 °C and slowly poured into 200 mL of ice water. The precipitated white solid was collected by filtration to give 5-bromo-4-nitroimidazole (2.3 g, 87% yield). Mass spectrum (ESI-) m/z 191 ([M-H]-). 1H NMR (300 MHz, DMSO-d6) δ 7.99 (s, 1H).

References

[1] Patent: US2004/162285, 2004, A1
[2] Patent: US2004/87577, 2004, A1. Location in patent: Page 122-123
[3] Journal of the American Chemical Society, 2001, vol. 123, # 49, p. 12147 - 12151

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