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

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

Uses

Used in Organic Synthesis:
1H-INDAZOLE, 3-BROMO-1-METHYL-7-NITROis used as a key intermediate in organic synthesis for the creation of novel compounds with various potential applications. Its unique structure allows for the development of new chemical entities with specific properties and functions.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 1H-INDAZOLE, 3-BROMO-1-METHYL-7-NITROis utilized as a starting material or building block in the development of new drugs and biologically active molecules. Its versatility and unique properties contribute to the discovery and design of innovative therapeutic agents with potential applications in various medical fields.
Used in Drug Development:
1H-INDAZOLE, 3-BROMO-1-METHYL-7-NITROplays a crucial role in drug development as a precursor for the synthesis of pharmaceutical compounds. Its unique chemical structure and properties enable the creation of new drug candidates with improved efficacy, selectivity, and safety profiles.
Used in Biological Research:
In biological research, 1H-INDAZOLE, 3-BROMO-1-METHYL-7-NITROis employed as a tool compound to study the mechanisms of action, target identification, and biological activity of various molecular pathways. Its unique structure allows researchers to probe and understand complex biological processes and develop targeted therapeutic strategies.

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.

Fluorinated indazoles as novel selective inhibitors of nitric oxide synthase (NOS): Synthesis and biological evaluation

In order to find new compounds with neuroprotective activity and NOS-I/NOS-II selectivity, we have designed, synthesized, and characterized 14 new NOS inhibitors with an indazole structure. The first group corresponds to 4,5,6,7-tetrahydroindazoles (4-8), the second to the N-methyl derivatives (9-12) of 7-nitro-1H-indazole (1) and 3-bromo-7-nitro-1H-indazole (2), and the latter to 4,5,6,7-tetrafluoroindazoles (13-17). Compound 13 (4,5,6,7-tetrafluoro-3-methyl-1H-indazole) inhibited NOS-I by 63% and NOS-II by 83%. Interestingly, compound 16 (4,5,6,7-tetrafluoro-3-perfluorophenyl-1H-indazole) inhibited NOS-II activity by 80%, but it did not affect to NOS-I activity. Structural comparison between these new indazoles further supports the importance of the aromatic indazole skeleton for NOS inhibition and indicate that bulky groups or N-methylation of 1 and 2 diminish their effect on NOS activity. The fluorination of the aromatic ring increased the inhibitory potency and NOS-II selectivity, suggesting that this is a promising strategy for NOS selective inhibitors.

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.

New and efficient synthesis of bi- and trisubstituted indazoles

In this paper, the synthesis of bi- and trisubstituted indazoles was described. 4-Alkoxy-7-aminoprotected-indazole or 7-aminoprotected-indazole derivatives were prepared selectively using SnCl2 in alcohol or SnCl2 in ethyl acetate, r