74420-02-3

Basic information

• Product Name: 4-HYDROXY-7-AZAINDOLE
• Synonyms: 4-HYDROXY-7-AZAINDOLE;1H-PYRROLO[2,3-B]PYRIDIN-4-OL;7-H-PYRROLO [2-3-B] PYRIDINE-4-OL;4-Hydroxy-7-aza-1H-indole;1H-Pyrrolo2,3-bpyridin-4-ol hydrate
• CAS NO: 74420-02-3
• Molecular Formula: C₇H₆N₂O
• Molecular Weight: 134.14
• EINECS: 1533716-785-6
• Product Categories: Azaindoles
• Mol File: 74420-02-3.mol

Chemical Properties

• Melting Point: 238-239 °C (decomp)
• Boiling Point: 367.6±42.0 °C(Predicted)
• Appearance: /
• Density: 1.434 g/cm³
• Refractive Index: 1.76
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 6.13±0.20(Predicted)
• CAS DataBase Reference: 4-HYDROXY-7-AZAINDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-HYDROXY-7-AZAINDOLE(74420-02-3)
• EPA Substance Registry System: 4-HYDROXY-7-AZAINDOLE(74420-02-3)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22
• Safety Statements: 24/25
• HazardClass: IRRITANT
• Hazardous Substances Data: 74420-02-3(Hazardous Substances Data)

Usage

Uses

Used in Chemical Sensing Applications:
4-HYDROXY-7-AZAINDOLE is used as a high-performance polyazaindole for its novel acid fluorescent sensor with a tunable ICT (Intramolecular Charge Transfer) effect. This characteristic makes it a valuable compound for detecting and monitoring various chemical species, contributing to advancements in chemical sensing technology.
Used in Pharmaceutical Industry:
4-HYDROXY-7-AZAINDOLE is used as a reactant in the design and synthesis of potent and selective azaindole-based Rho kinase (ROCK) inhibitors. These inhibitors play a crucial role in the development of new therapeutic strategies for various diseases, as they target specific protein kinases involved in cellular signaling pathways, potentially leading to more effective treatments with fewer side effects.

InChI:InChI=1/C7H6N2O/c10-6-2-4-9-7-5(6)1-3-8-7/h1-4H,(H2,8,9,10)

Upstream product

• 55052-28-3 4-chloro-7-azaindole 
• 74420-00-1 4-amino-1H-pyrrolo<2,3-b>pyridine 

Downstream Products

• 122379-57-1 1-p-Tolyl-1H-pyrrolo[3,2-c]pyridin-4-ylamine 
• 122379-53-7 1-(4-Chloro-phenyl)-1H-pyrrolo[3,2-c]pyridin-4-ylamine 
• 122379-59-3 1-(4-Methoxy-phenyl)-1H-pyrrolo[3,2-c]pyridin-4-ylamine 
• 122379-55-9 1-(4-nitrophenyl)-1H-pyrrolo[3,2-c]pyridin-4-amine 
• 122379-49-1 4-amino-1-phenyl-1H-pyrrolo<3,2-c>pyridine 
• 930576-14-0 4-(1H-pyrrolo[2,3-a]pyridin-4-yloxy)-2,5-difluoro-N-(1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridin-3-yl)benzamide, trifluoroacetic acid salt 
• 1011711-57-1 4-ethoxy-1H-pyrrolo[2,3-b]pyridine 
• 937797-32-5 4-(1-methylethoxy)-1H-pyrrolo[2,3-b]pyridine 

Relevant articles and documents

Concise and Efficient Synthesis of 4-Fluoro-1H-pyrrolo[2,3-b]pyridine

(Equation presented) Two routes describing the preparation of 4-fluoro-1H-pyrrolo[2,3-b]pyridine (4a) from 1H-pyrrolo[2,3-b]pyridine N-oxide (1) are presented. Regioselective fluorination was achieved using either the Balz-Schiemann reaction or lithium-halogen exchange.

The Synthesis of 5-Azaindoles by Substitution-Rearrangement of 7-Azaindoles upon Treatment with Certain Primary Amines

Certain 4-substituted 1H-pyrrolopyridines (7-azaindoles) undergo a nucleophilic substitution-rearrangement upon treatment with various primary amines at elevated temperatures to yield N-1-substituted 4-amino-1H-pyrrolopyridines (5-azaindoles).Treatment of the same 7-azaindoles with secondary amines under the same reaction conditions led to simple nucleophilic substitution products.