2-Chloro-4-nitroimidazole Chemical Properties

Melting point:

216-217 °C

Boiling point:

386.8±34.0 °C(Predicted)

Density 

1.740±0.06 g/cm3(Predicted)

storage temp. 

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

solubility 

DMSO (Slightly, Sonicated), Methanol (Slightly, Sonicated)

pka

5.65±0.10(Predicted)

form 

Solid

color 

Off-White to Pale Beige

InChI

InChI=1S/C3H2ClN3O2/c4-3-5-1-2(6-3)7(8)9/h1H,(H,5,6)

InChIKey

BOJZBRDIZUHTCE-UHFFFAOYSA-N

SMILES

C1(Cl)NC([N+]([O-])=O)=CN=1

CAS DataBase Reference

57531-37-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

HazardClass 

IRRITANT

HS Code 

2933299090

2-Chloro-4-nitroimidazole Usage And Synthesis

Chemical Properties

Light yellow solid

Uses

4-Nitroimidazole derivative with poetenial use as radiosensitizers of hypoxic cells. It is used in the preparation of antitubercular nitroimidazoles.

Uses

4-Nitroimidazole derivative with poetenial use as radiosensitizers of hypoxic cells. 2-Chloro-4-nitroimidazole is used in the preparation of antitubercular nitroimidazoles.

Synthesis

Example 9 Preparation of 2-chloro-4-nitroimidazole: 2-chloro-5-iodo-4-nitroimidazole (273 mg, 1.0 mmol) was dissolved in anhydrous ethanol (5 mL), followed by sequential addition of triethylamine (420 μL, 3.0 mmol) and 10% palladium-carbon catalyst (27 mg) to the solution. The reaction mixture was hydrogenated by stirring for 3 hours at room temperature and under an atmosphere of hydrogen at atmospheric pressure. Upon completion of the reaction, the catalyst was removed by filtration and the filtrate was concentrated under reduced pressure to afford the colorless solid product 2-chloro-4-nitroimidazole (124 mg, 84.1% yield). The product was characterized by 1H-NMR (DMSO-d6): δ 8.44 (1H, s), 14.19 (1H, bs). Example 11 Preparation of 2-chloro-4-nitroimidazole: 2-chloro-5-iodo-4-nitroimidazole (545 mg, 2.0 mmol) was dissolved in anhydrous ethanol (10 mL), followed by sequential addition of triethylamine (840 μL, 6.0 mmol) and 10% palladium-carbon catalyst (54 mg) to the solution. The reaction mixture was hydrogenated under hydrogen pressure of 4 kg/cm2 in a pearl reduction apparatus. Upon completion of the reaction, the catalyst was removed by filtration and the filtrate was concentrated under reduced pressure to give the colorless solid product 2-chloro-4-nitroimidazole (246 mg, 83.4% yield). The product was characterized by 1H-NMR (DMSO-d6): δ 8.44 (1H, s), 14.19 (1H, bs).

References

[1] Patent: WO2005/77913, 2005, A1. Location in patent: Page/Page column 76-77
[2] Patent: EP1553088, 2005, A1. Location in patent: Page/Page column 58-59
[3] Patent: EP1553088, 2005, A1. Location in patent: Page/Page column 58
[4] Patent: EP1553088, 2005, A1. Location in patent: Page/Page column 59

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