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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

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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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Alane Beatriz Vermelho et al.
Journal of enzyme inhibition and medicinal chemistry, 33(1), 139-146 (2017-12-02)
Sulfonamide carbonic anhydrase (CA, EC 4.2.1.1) inhibitors targeting the α-class enzyme from the protozoan pathogen Trypanosoma cruzi, responsible of Chagas disease, were recently reported. Although many such derivatives showed low nanomolar activity in vitro, they were inefficient anti-T. cruzi agents
Kazuki Yoshihara et al.
Chembiochem : a European journal of chemical biology, 18(16), 1650-1658 (2017-05-16)
The use of DNA aggregates could be a promising strategy for the molecular imaging of biological functions. Herein, phosphorescent oligodeoxynucleotides were designed with the aim of visualizing oxygen fluctuation in tumor cells. DNA-ruthenium conjugates (DRCs) that consisted of oligodeoxynucleotides, a
J. Chem. Res. Synop., 92-92 (1993)
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
Christin Glowa et al.
Radiation oncology (London, England), 12(1), 174-174 (2017-11-11)
To summarize the research activities of the "clinical research group heavy ion therapy", funded by the German Research Foundation (DFG, KFO 214), on the impact of intrinsic tumor characteristics (grading, hypoxia) on local tumor control after carbon ( Three sublines
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