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195650

Sigma-Aldrich

2-Nitroimidazole

98%

Synonym(s):

Azomycin

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About This Item

Empirical Formula (Hill Notation):
C3H3N3O2
CAS Number:
527-73-1
Molecular Weight:
113.07
Beilstein/REAXYS Number:
116444
EC Number:
208-425-5
MDL number:
MFCD00005185
UNSPSC Code:
12352005
PubChem Substance ID:
24851703
NACRES:
NA.22

assay

98%

form

solid

mp

287 °C (dec.) (lit.)

SMILES string

[O-][N+](=O)c1ncc[nH]1

InChI

1S/C3H3N3O2/c7-6(8)3-4-1-2-5-3/h1-2H,(H,4,5)

InChI key

YZEUHQHUFTYLPH-UHFFFAOYSA-N

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General description

2-Nitroimidazole is a natural antibiotic.

Application

2-Nitroimidazole was used in the synthesis of:
  • tert-butyl 2-(2-nitro-1H-imidazol-1-yl)ethylcarbamate
  • 1-(2-(tert-butyldimethylsilyloxy)ethyl)-2-nitro-1H-imidazole
  • 2-fluoro-N-(2-(2-nitro-1H-imidazol-1-yl)ethyl)acetamide
  • 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl 2-fluoroacetate
  • radiolabeling precursors - the bromo substituted analogs
  • nitroimidazole substituted boronic acids, precursors for imaging hypoxic tissue
  • potential site-selective radiosensitizers for estrogen receptor-rich tumors

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Analysis Note

solubility :
50 mg/mL in NH4OH : soluble, clear, green-yellow, to very dark green-yellow to very dark yellow

related product

Product No.
Description
Pricing

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Certificates of Analysis (COA)

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Zhihao Zha et al.
Nuclear medicine and biology, 38(4), 501-508 (2011-05-03)
Nitroimidazole (azomycin) derivatives labeled with radioisotopes have been developed as cancer imaging and radiotherapeutic agents based on the oncological hypoxic mechanism. By attaching nitroimidazole core with different functional groups, we synthesized new nitroimidazole derivatives and evaluated their potentiality as tumor
Tetrahedron, 48, 10233-10233 (1992)
R K Jackson et al.
Clinical oncology (Royal College of Radiologists (Great Britain)), 31(5), 290-302 (2019-03-12)
The role of hypoxia in radiation resistance is well established and many approaches to overcome hypoxia in tumours have been explored, with variable success. Two small molecule strategies for targeting hypoxia have dominated preclinical and clinical efforts. One approach has
Bryce E Kidd et al.
The journal of physical chemistry. C, Nanomaterials and interfaces, 122(29), 16848-16852 (2018-12-19)
We report a simple and effective method to remove IrIMes homogeneous polarization transfer catalysts from solutions where NMR Signal Amplification By Reversible Exchange (SABRE) has been performed, while leaving intact the substrate's hyperpolarized state. Following microTesla SABRE hyperpolarization of 15N
Yi Qu et al.
Environmental microbiology, 13(4), 1010-1017 (2011-01-20)
Antibiotic resistance in pathogens can be mediated by catabolic enzymes thought to originate from soil bacteria, but the physiological functions and evolutionary origins of the enzymes in natural ecosystems are poorly understood. 2-Nitroimidazole (2NI) is a natural antibiotic and an
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