92-25-1

Basic information

• Product Name: 8-amino-7-methylphenazin-2-ol
• Synonyms: 8-amino-7-methylphenazin-2-ol;2-Amino-3-methylphenazin-8-ol;3-Amino-2-methylphenazin-7-ol;7-Methyl-8-aminophenazine-2-ol;8-amino-7-methyl-10H-phenazin-2-one;8-azanyl-7-methyl-10H-phenazin-2-one;KWBJTBKOXIZLGY-UHFFFAOYSA-N
• CAS NO: 92-25-1
• Molecular Formula: C₁₃H₁₁N₃O
• Molecular Weight: 225.24594
• EINECS: 202-139-4
• Mol File: 92-25-1.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 439.8°C at 760 mmHg
• Flash Point: 219.8°C
• Appearance: /
• Density: 1.41g/cm³
• Vapor Pressure: 6.2E-08mmHg at 25°C
• Refractive Index: 1.73
• CAS DataBase Reference: 8-amino-7-methylphenazin-2-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 8-amino-7-methylphenazin-2-ol(92-25-1)
• EPA Substance Registry System: 8-amino-7-methylphenazin-2-ol(92-25-1)

Safety Data

• Hazardous Substances Data: 92-25-1(Hazardous Substances Data)

Usage

Description

8-amino-7-methylphenazin-2-ol, also known as methylene blue, is a synthetic chemical compound that serves as both a dye and a medication. It functions as a redox indicator and is characterized by its ability to stain and differentiate between living and dead bacteria in microbiology laboratories. Methylene blue is also recognized for its therapeutic uses, particularly in treating methemoglobinemia, a condition that impairs hemoglobin's oxygen-carrying capacity. Furthermore, it has been explored for its potential in managing neurodegenerative diseases and as an antimalarial agent. However, it is crucial to exercise caution with methylene blue, as improper use can lead to adverse effects.

Uses

Used in Microbiology:
8-amino-7-methylphenazin-2-ol is used as a staining agent for the determination of dead or living bacteria in microbiology laboratories. It aids in the differentiation of bacterial populations, which is essential for accurate microbiological analysis.
Used in Medical Treatments:
8-amino-7-methylphenazin-2-ol is used as a medication to treat methemoglobinemia, a condition characterized by a reduced oxygen-carrying capacity of hemoglobin. It helps restore normal hemoglobin function, thereby improving oxygen transport in the blood.
Used in Neurodegenerative Disease Research:
8-amino-7-methylphenazin-2-ol is being investigated for its potential applications in the treatment of neurodegenerative diseases. Its possible neuroprotective properties are of interest to researchers seeking new therapeutic approaches for such conditions.
Used in Antimalarial Drug Development:
8-amino-7-methylphenazin-2-ol has been explored as a potential antimalarial agent. Its effectiveness against malaria parasites is under investigation, with the aim of developing new treatments for malaria.
Used in Dye Industry:
As a synthetic dye, 8-amino-7-methylphenazin-2-ol is used in various applications within the dye industry, including coloring textiles, paper, and other materials. Its versatility as a dye makes it a valuable compound in this sector.

InChI:InChI=1/C13H11N3O/c1-7-4-11-13(6-9(7)14)16-12-5-8(17)2-3-10(12)15-11/h2-6,16H,14H2,1H3

Upstream product

• 121-23-3 [1,4]benzoquinone-mono-(2,4-diamino-5-methyl-phenylimine) 
• 95-80-7 4-methylbenzene-1,3-diamine 
• 123-30-8 4-amino-phenol 

Relevant articles and documents

Eco-friendly synthesis of indo dyes mediated by a bacterial laccase

Several aminoindamine and indoaniline dyes were obtained in good to excellent yields (64-98%) by oxidative cross-coupling between 1,4-phenylenediamine (1), 4-aminophenol (2) or 2,5-diaminotoluene (3) and several meta- and meta,para-substituted couplers (4a-j) using a green biocatalyst, the bacterial enzyme CotA-laccase from Bacillus subtilis, in water and under mild conditions of pH and temperature. Our results show that the enzymatic route described represents an efficient and sustainable alternative to the chemical synthesis of indo dyes, with a potentially high impact in the cosmetic and hair dye industries.