531-55-5

Basic information

• Product Name: Azure B
• Synonyms: N,N,N'-TRIMETHYLTHIONIN;3-(dimethylamino)-7-(methylamino)-phenothiazin-5-iumchloride;3-(dimethylamino)-7-(methylimino)-3h-phenothiazinehydrochloride;3-(dimethylamino)-7-(methylimino)-3h-phenothiazinhydrochloride;3-methylamino-7-dimethylaminophenzathoniumchloride;modrkresylovabb;Phenothiazin-5-ium,3-(dimethylamino)-7-(methylamino)-,chloride;trimethylthioninechloride
• CAS NO: 531-55-5
• Molecular Formula: C₁₅H₁₆N₃S*Cl
• Molecular Weight: 305.83
• EINECS: 208-511-2
• Product Categories: Phenothiazine
• Mol File: 531-55-5.mol
• Article Data: 2

Chemical Properties

• Melting Point: 205-210 °C (dec.)(lit.)
• Appearance: Dark green/Powder
• Storage Temp.: -20°C Freezer
• Solubility: H2O: soluble1mg/mL
• Water Solubility: Soluble
• Stability: Stable. Incompatible with strong oxidizing agents.
• Merck: 14,6058
• BRN: 3922630
• CAS DataBase Reference: Azure B(CAS DataBase Reference)
• NIST Chemistry Reference: Azure B(531-55-5)
• EPA Substance Registry System: Azure B(531-55-5)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• RTECS: SO5550000
• Hazardous Substances Data: 531-55-5(Hazardous Substances Data)

Usage

Description

Azure B, also known as Methylene Blue, is an organic chloride salt with the counterion 3-(dimethylamino)-7-(methylamino)phenothiazin-5-ium. It is a green crystalline powder that is widely used as a biological stain and has various applications in different fields.

Uses

Used in Medical Applications:
Azure B is used as a staining agent for reticulocytes in blood smears, aiding in the identification and analysis of these cells.
Used in Histopathology:
Azure B is used as a biological stain for staining semi-thin sections of plant tissue, as well as for blood smears in the NCCLS method and paraffin sections in Lillie's modified Nocht's method. These staining techniques are essential for the examination of tissue samples in histopathology.
Used in Research:
Azure B serves as an active metabolite of methylene blue, which is used in various research applications, including the study of cellular respiration and the assessment of mitochondrial function.
Used in Pharmaceutical Industry:
Azure B is used in the preparation of azure eosin stains, which are essential for staining blood smears in diagnostic laboratories. This application is crucial for the accurate diagnosis of various blood-related disorders and conditions.
Used in Microbiology:
Azure B is employed as a staining agent in microbiology for the visualization of microorganisms, such as bacteria and fungi, in samples. This staining technique helps researchers and medical professionals identify and study the morphology and characteristics of these microorganisms.

Biochem/physiol Actions

Azure B is a cationic dye. It is part of the Romanowsky stain, which is used for staining of blood films. It is also used for the localization of nucleic acids and lignin.

Purification Methods

Azure B has been twice recrystallised from H2O and dried at 100o/1hour in an oven. [Beilstein 27 III/IV 5151.]

InChI:InChI=1/C15H16N3S.ClH/c1-16-10-4-6-12-14(8-10)19-15-9-11(18(2)3)5-7-13(15)17-12;/h4-9,16H,1-3H3;1H/q+1;/p-1

Synthetic route

3,7-bis(dimethylamine)phenothiazonium (807306-71-4) → azure A (531-53-3) + azure B (531-55-5)

Conditions	Yield
With pyridine; air; copper Behandeln des Reaktionsprodukts mit wss. HCl;

3,7-bis(dimethylamine)phenothiazonium (807306-71-4) → azure B (531-55-5) + 2-amino-7-dimethylamino-phenazthionium chloride ; 7-dimethylamino-2-oxy-phenazthionium chloride

Conditions	Yield
With silver(l) oxide Zusatz von Salzsaeure und Kochsalz zu dem aufgearbeiteten Reaktionsprodukt;

4-amino-N,N-dimethylaniline (99-98-9) → azure B (531-55-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogen sulfide / man faellt aus der Loesung das Methylenblau mit Zinkchlorid und Kochsalz aus 2: silver oxide / Zusatz von Salzsaeure und Kochsalz zu dem aufgearbeiteten Reaktionsprodukt View Scheme

methylene blue (152071-32-4) → azure B (531-55-5)

Conditions	Yield
With manganese(II,III) oxide at 20℃; for 0.0833333h; Reagent/catalyst;

azure B (531-55-5) + [11C]methyl triflate (145577-00-0) → [N-methyl-11C]methylene blue

Conditions	Yield
With potassium carbonate at 20℃; for 0.0833333h;

[11C]methyl trifluoromethanesulfonate (165378-76-7) + azure B (531-55-5) → [N-methyl-11C]methylene blue

Conditions	Yield
With potassium carbonate In water at 20℃; for 0.0833333h;

Upstream product

• 152071-32-4 methylene blue 
• 99-98-9 4-amino-N,N-dimethylaniline 
• 807306-71-4 3,7-bis(dimethylamine)phenothiazonium 

Relevant articles and documents

HPLC-MS and UV–Visible Coupled Analysis of Methylene Blue Photodegradation by Hydrothermally Grown ZnO Nanowires

Photocatalysis is an efficient and promising method to purify water. Numerous studies have been dedicated to demonstrate its efficiency on several hazardous compounds, derived from various industries. However, even if the degradation of such products has been extensively studied, obtaining information on their photodegradation pathway is still challenging, leading to concerns about the innocuousness of the treated water. In this study, the authors use ZnO nanowires (ZnO NWs), to photodegrade a solution of the commonly used organic dye methylene blue (MB) under ultraviolet (UV) irradiation, followed simultaneously by UV-visible (UV-vis) spectrometry and high-performance liquid chromatography coupled with mass spectrometry (HPLC-MS). Combining these two methods real-time information on the photodegradation efficiency and degradation mechanism are given. The HPLC-MS analysis allows us to confidently identify three reaction intermediates of the MB degradation: Azure A, B and C, as well as spot three other compounds, with uncertain formulas, leading to the presented hypothesis on the beginning of the MB degradation pathway. While the UV-visible analysis shows a total degradation of MB after 2 h of photodegradation, the HPLC-MS analysis indicates that some MB remain in the solution. Its quantity is calculated to be 14 μg L?1, which is harmless to humans.