74209-37-3

Basic information

• Product Name: 1H-INDAZOLE, 3-BROMO-1-METHYL-7-NITRO-
• Synonyms: 1H-INDAZOLE, 3-BROMO-1-METHYL-7-NITRO-;3-Bromo-1-methyl-7-nitro-1H-indazole
• CAS NO: 74209-37-3
• Molecular Formula: C8H6BrN3O2
• Molecular Weight: 256.058
• Mol File: 74209-37-3.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 388.286 °C at 760 mmHg
• Flash Point: 188.629 °C
• Appearance: /
• Density: 1.87 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.725
• CAS DataBase Reference: 1H-INDAZOLE, 3-BROMO-1-METHYL-7-NITRO-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-INDAZOLE, 3-BROMO-1-METHYL-7-NITRO-(74209-37-3)
• EPA Substance Registry System: 1H-INDAZOLE, 3-BROMO-1-METHYL-7-NITRO-(74209-37-3)

Safety Data

• Hazardous Substances Data: 74209-37-3(Hazardous Substances Data)

Usage

General Description

1H-INDAZOLE, 3-BROMO-1-METHYL-7-NITRO- is a specific chemical compound with the molecular formula C9H7BrN4O2. It is classified as an indazole derivative and contains a nitro group, a bromine atom, and a methyl group. 1H-INDAZOLE, 3-BROMO-1-METHYL-7-NITRO- is commonly used in organic synthesis and pharmaceutical research, with potential applications in the development of new drugs and biologically active molecules. Its unique structure and properties make it a valuable and versatile building block for the creation of novel compounds with various potential uses.

InChI:InChI=1/C8H6BrN3O2/c1-11-7-5(8(9)10-11)3-2-4-6(7)12(13)14/h2-4H,1H3

Upstream product

• 74209-34-0 3-bromo-7-nitro-1H-indazole 
• 74-88-4 methyl iodide 
• 2942-42-9 7-Nitroindazole 

Relevant articles and documents

Crystal and molecular structure of three biologically active nitroindazoles

3-Bromo-1-methyl-7-nitro-1H-indazole (1), 3-bromo-2-methyl-7-nitro-2H- indazole (2) and 3,7-dinitro-1(2)H-indazole (3) have been synthesized and characterized by X-ray diffraction, 13C and 15N NMR spectroscopy in solution and in solid-state. The dihedral angles obtained in the crystal structures are in good agreement with the molecular parameters calculated using DFT B3LYP calculations employing the 6-311++G(d,p) basis set. Compounds 1 and 2 present intermolecular halogen bonds between the bromine and the oxygen atoms of the nitro group and in compound 3 inter- and intramolecular hydrogen bonding exists.

Inhibitory effects of a series of 7-substituted-indazoles toward nitric oxide synthases: Particular potency of 1H-indazole-7-carbonitrile

A series of new 7-monosubstituted and 3,7-disubstituted indazoles have been prepared and evaluated as inhibitors of nitric oxide synthases (NOS). 1H-Indazole-7-carbonitrile (6) was found equipotent to 7-nitro-1H-indazole (1) and demonstrated preference for constitutive NOS over inducible NOS. By contrast, 1H-indazole-7-carboxamide (8) was slightly less potent but demonstrated a surprising selectivity for the neuronal NOS. Further substitution of 6 by a Br-atom at carbon-3 of the heterocycle enhanced 10-fold the inhibitory effects. Inhibition of NO formation by 6 appeared to be competitive versus both substrate and the cofactor (6R)-5,6,7,8-tetrahydro-l-biopterin (H4B). In close analogies with 1, compound 6 strongly inhibited the NADPH oxidase activity of nNOS and induced a spin state transition of the heme-FeIII. Our results are explained with the help of the X-ray structures that identified key-features for binding of 1 at the active site of NOS.