216755
5-Nitroindazole
≥99%
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About This Item
Empirical Formula (Hill Notation):
C7H5N3O2
CAS Number:
Molecular Weight:
163.13
EC Number:
226-451-5
UNSPSC Code:
12352100
PubChem Substance ID:
Beilstein/REAXYS Number:
7936
MDL number:
assay
≥99%
form
powder
mp
204-208 °C (lit.)
SMILES string
[O-][N+](=O)c1ccc2[nH]ncc2c1
InChI
1S/C7H5N3O2/c11-10(12)6-1-2-7-5(3-6)4-8-9-7/h1-4H,(H,8,9)
InChI key
WSGURAYTCUVDQL-UHFFFAOYSA-N
General description
5-Nitroindazole inhibits citrulline formation by Ca2+-calmodulin (CaM)-dependent nitric oxide synthase from bovine brain. Nitration of 5-nitroindazole with nitric acid and acetic anhydride yields 3,5-dintroindazole and 2,5-dinitroindazole.
signalword
Warning
hcodes
Hazard Classifications
Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 2
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Faceshields, Gloves
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Nitration of indazoles in the 3 position.
Habraken CL and Cohen-Fernandes P.
The Journal of Organic Chemistry, 36(21), 3084-3086 (1971)
D J Wolff et al.
Archives of biochemistry and biophysics, 311(2), 300-306 (1994-06-01)
Citrulline formation by Ca(2+)-calmodulin (CaM)-dependent nitric oxide synthase from bovine brain is inhibited reversibly by indazole, 5-nitro-, 6-nitro-, and 7-nitroindazole with IC50 values of 2.3 mM, 1.15 mM, 40 microM, and 2.5 microM, respectively. Inhibition of citrulline formation by 7-nitroindazole
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