2-Nitroimidazole Chemical Properties

Melting point:

287 °C (dec.) (lit.)

Boiling point:

211.75°C (rough estimate)

Density 

1.5988 (rough estimate)

refractive index 

1.4264 (estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

NH4OH: soluble50mg/mL, clear, yellow to orange

form 

Powder

pka

8.72±0.10(Predicted)

color 

Light yellow to khaki-green

Water Solubility 

insoluble

Merck 

14,921

BRN 

116444

InChIKey

YZEUHQHUFTYLPH-UHFFFAOYSA-N

CAS DataBase Reference

527-73-1(CAS DataBase Reference)

EPA Substance Registry System

1H-Imidazole, 2-nitro- (527-73-1)

Safety Information

Hazard Codes 

Xn,T

Risk Statements 

22-36/37/38-23/24/25-20/21/22

Safety Statements 

26-36-45-36/37/39

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

3

RTECS 

NI7875000

TSCA 

Yes

HazardClass 

6.1

PackingGroup 

III

HS Code 

29332990

Toxicity

LD50 i.v. in mice: 80 mg/kg (Maeda)

MSDS

• Language:English Provider:Azomycin
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

2-Nitroimidazole Usage And Synthesis

Chemical Properties

Pale Yellow Solid

Uses

2-Nitroimidazole, is used as an antibiotic in pharma industry.

Uses

2-Nitroimidazole is a antibiotic substance produced by an unidentified Streptomyces,it is used to prepare nitroimidazole substituted boronic acids as precursors for imaging hypoxic tissue 1.It is also used to prepare potential site-selective radiosensitizers for estrogen receptor-rich tumors.

Definition

ChEBI: An imidazole that is 1H-imidazole substituted at position 2 by a nitro group.

General Description

2-Nitroimidazole is a natural antibiotic.

Synthesis

General procedure for the synthesis of 2-nitroimidazole from 2-aminoimidazole sulfate: 2-aminoimidazole sulfate (1.57 g, 6.01 mmol) was dissolved in water (10 mL) and 50% w/v fluoroboric acid (7 mL). The reaction solution was cooled to -20 °C in an acetone/dry ice bath and a solution of sodium nitrite (4.14 g, 59.6 mmol) in water (10 mL) was added slowly and dropwise. The reaction temperature was maintained at -10 °C and stirred for 30 min. Subsequently, the reaction solution was poured into a solution of copper sulfate (20.0 g, 119 mmol) in water (200 mL). Sodium nitrite (4.14 g, 59.6 mmol) was then added and the reaction mixture was stirred for 2 hours at room temperature. After completion of the reaction, the extract was carried out for 6 hours using a continuous extractor with ethyl acetate (200 mL) as the extractant. The organic phases were combined, concentrated under reduced pressure and the residue was recrystallized from ethanol to give the target compound 2-nitroimidazole as yellow needle-like crystals (870 mg, 65% yield).

References

[1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 17, p. 5102 - 5106

2-Nitroimidazole(527-73-1)Related Product Information

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• TRITON
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• 8-Bromo-6-nitroimidazo[1,2-a]pyridine
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