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MilliporeSigma

195650

Sigma-Aldrich

2-Nitroimidazole

98%

Synonym(s):

Azomycin

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250 MG
$57.10
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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

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Quality Level

200

assay

98%

form

solid

mp

287 °C (dec.) (lit.)

functional group

nitro

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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Show Differences

1 of 4

This Item
136255N7778141615
2-Nitroimidazole 98%

Sigma-Aldrich

195650

2-Nitroimidazole

2-Methyl-4(5)-nitroimidazole 99%

Sigma-Aldrich

136255

2-Methyl-4(5)-nitroimidazole

7-Nitroindazole ≥98%

Sigma-Aldrich

N7778

7-Nitroindazole

4-Nitroimidazole 97%

Sigma-Aldrich

141615

4-Nitroimidazole

assay

98%

assay

99%

assay

≥98%

assay

97%

Quality Level

200

Quality Level

200

Quality Level

100

Quality Level

200

mp

287 °C (dec.) (lit.)

mp

251-255 °C (lit.)

mp

-

mp

303 °C (dec.) (lit.)

form

solid

form

powder

form

powder

form

powder

functional group

nitro

functional group

nitro

functional group

-

functional group

nitro

General description

2-Nitroimidazole is a natural antibiotic[1].

Application

2-Nitroimidazole was used in the synthesis of:
  • tert-butyl 2-(2-nitro-1H-imidazol-1-yl)ethylcarbamate[2]
  • 1-(2-(tert-butyldimethylsilyloxy)ethyl)-2-nitro-1H-imidazole[2]
  • 2-fluoro-N-(2-(2-nitro-1H-imidazol-1-yl)ethyl)acetamide[2]
  • 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl 2-fluoroacetate[2]
  • radiolabeling precursors - the bromo substituted analogs[2]
  • nitroimidazole substituted boronic acids, precursors for imaging hypoxic tissue[3]
  • potential site-selective radiosensitizers for estrogen receptor-rich tumors[4]

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCN6941
BCCM3518
BCCK0234
BCCL0276
BCCJ8327

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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
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
Tetrahedron, 48, 10233-10233 (1992)
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
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
View All Related Papers

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