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655-86-7 Usage

Description

2,3-Diaminophenazine is a brown to yellow needles. On heating sublimes forming yellow leaflets. mp 264°. Sol in alcohol, benzene. Yields 2-aminophenazine and small amounts of phenazine when heated with zinc dust.It is used for detection of bismuth, cadmium, lead, copper, and mercury.

Chemical Properties

Yellow to light brown needle-like crystals

Uses

2,3-Phenazinediamine is used for the study on detection of HIV-1 p24 antigen in patients with varying degrees of viremia using ELISA with photochemical signal amplication system.

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 26, p. 1163, 1989 DOI: 10.1002/jhet.5570260447

Safety Profile

Mutation data reported. When heated to decomposition it emits toxic vapors of NOx.

Check Digit Verification of cas no

The CAS Registry Mumber 655-86-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,5 and 5 respectively; the second part has 2 digits, 8 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 655-86:
(5*6)+(4*5)+(3*5)+(2*8)+(1*6)=87
87 % 10 = 7
So 655-86-7 is a valid CAS Registry Number.
InChI:InChI=1/C12H10N4/c13-7-5-11-12(6-8(7)14)16-10-4-2-1-3-9(10)15-11/h1-6H,13-14H2

655-86-7 Well-known Company Product Price

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  • Aldrich

  • (661376)  2,3-Diaminophenazine  90%

  • 655-86-7

  • 661376-5G

  • 925.47CNY

  • Detail
  • Aldrich

  • (661376)  2,3-Diaminophenazine  90%

  • 655-86-7

  • 661376-25G

  • 3,111.03CNY

  • Detail

655-86-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Phenazine-2,3-diamine,2,3-Diaminophenazine

1.2 Other means of identification

Product number -
Other names 2,3-Diaminophenazine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:655-86-7 SDS

655-86-7Relevant articles and documents

Generation of Reactive Oxygen Species via Electroprotic Interaction of H2O2 with ZrO2 Gel: Ionic Sponge Effect and pH-Switchable Peroxidase- and Catalase-Like Activity

Sobańska, Kamila,Pietrzyk, Piotr,Sojka, Zbigniew

, p. 2935 - 2947 (2017)

Formation of reactive oxygen species (ROS) is of vital importance in catalytic oxidation chemistry. In this paper we have shown that a nonredox system such as amorphous zirconium dioxide (a-ZrO2) is highly active in ROS formation via H2O2 decomposition. Interaction between a-ZrO2 and H2O2 in aqueous solution was investigated by means of EPR, HYSCORE, Raman, and UV-vis, along with auxiliary FTIR, TG-MS, and XPS techniques, in a broad range of pH values and H2O2 concentrations. Various reaction intermediates such as superoxide (O2?-) and hydroxyl (?OH) radicals as well as peroxide (O22-) species were identified. At pH 2 gel exhibited peroxidase-type activity, quantified by an o-phenylenediamine assay. At pH >5.3 formation of O22- is accompanied by a substantial release of O2 due to the pronounced catalase-like activity of a-ZrO2. The role of electroprotic processes (an interfacial proton transfer coupled with an intermolecular electron transfer) in H2O2 decomposition and ROS formation was elucidated, and a plausible mechanism of this reaction, ≡Zr+-HO2-(surf) + H2O2(aq) → ?OH(aq) + ≡Zr+-O2?-(surf) + H2O, was proposed. The surface of a-ZrO2 covered with hydroxyl groups plays a role of an ionic sponge, which controls the electroprotic equilibrium by capturing the charged reaction intermediates. Unlike the amorphous gel, crystalline zirconia exhibits only weak activity in the production of the O2?- and ?OH radicals, and a different mechanism is involved. It is worth mentioning that the activity of the zirconia gel catalyst in ROS generation, as gauged by the Michaelis-Menten constant, is comparable (ca. 40%) to that of the Fenton-type oxides (Fe3O4, Co3O4).

Facile synthesis of a Fe3O4/MIL-101(Fe) composite with enhanced catalytic performance

Jiang, Zhong Wei,Dai, Fu Qiang,Huang, Cheng Zhi,Li, Yuan Fang

, p. 86443 - 86446 (2016)

A magnetic porous material, Fe3O4/MIL-101(Fe), has been successfully fabricated by using simple ultrasound-assisted electrostatic self-assembly technology, and was demonstrated to be a highly active heterogeneous catalyst for the dimerization reaction of o-phenylenediamine (OPD) in the presence of H2O2via synergistic peroxidase-like activity.

A nano-sized Cu-MOF with high peroxidase-like activity and its potential application in colorimetric detection of H2O2and glucose

Ren, Chunguang,Tian, Xuemei,Wang, Zhonghua,Wu, Hanliu,Yu, Hao,Zhou, Yafen

, p. 26963 - 26973 (2021)

Peroxidase widely exists in nature and can be applied for the diagnosis and detection of H2O2, glucose, ascorbic acid and other aspects. However, the natural peroxidase has low stability and its catalytic efficiency is easily affected by external conditions. In this work, a copper-based metal-organic framework (Cu-MOF) was prepared by hydrothermal method, and characterized by means of XRD, SEM, FT-IR and EDS. The synthesized Cu-MOF material showed high peroxidase-like activity and could be utilized to catalyze the oxidation ofo-phenylenediamine (OPDA) and 3,3′,5,5′-tetramethylbenzidine (TMB) in the presence of H2O2. The steady-state kinetics experiments of the oxidation of OPDA and TMB catalyzed by Cu-MOF were performed, and the kinetic parameters were obtained by linear least-squares fitting to Lineweaver-Burk plot. The results indicated that the affinity of Cu-MOF towards TMB and OPDA was close to that of the natural horseradish peroxidase (HRP). The as-prepared Cu-MOF can be applied for colorimetric detection of H2O2and glucose with wide linear ranges of 5 to 300 μM and 50 to 500 μM for H2O2and glucose, respectively. Furthermore, the specificity of detection of glucose was compared with other sugar species interference such as sucrose, lactose and maltose. In addition, the detection of ascorbic acid and sodium thiosulfate was also performed upon the inhibition of TMB oxidation. Based on the high catalytic activity, affinity and wide linear range, the as-prepared Cu-MOF may be used for artificial enzyme mimics in the fields of catalysis, biosensors, medicines and food industry.

Phenazine-2,3-diamine

Doyle, Robert P.,Kruger, Paul E.,Mackie, Philip R.,Nieuwenhuyzen, Mark

, p. 104 - 105 (2001)

The structure of the 2,3-diamino phenazine (DAP) in its non-protonated form was described. The crystal packing, which features π-π, hydrogen- and T-bonded interactions, was analyzed. The chemistry of the DAP was demonstrated using organic transformations. The characterization of the compound was done by nuclear magnetic resonance (NMR), absorption and emission techniques.

Fluorescent and Colorimetric Dual-Readout Assay for Inorganic Pyrophosphatase with Cu2+-Triggered Oxidation of o-Phenylenediamine

Sun, Jian,Wang, Bin,Zhao, Xue,Li, Zong-Jun,Yang, Xiurong

, p. 1355 - 1361 (2016)

We demonstrate a rationally designed fluorescent and colorimetric dual-readout strategy for the highly sensitive, quantitative determination of inorganic pyrophosphatase (PPase) activity, a key hydrolytic enzyme involved in a variety of metabolic processes. Inspired by the selective oxidative and chromogenic reaction of o-phenylenediamine (OPD) with Cu2+, the special inhibitory effects of pyrophosphate (PPi) on the oxidative ability of Cu2+, and the specific hydrolysis of PPi into orthophosphate by PPase, a convenient small molecule OPD-based analytical system was developed for Cu2+/PPi recognition and PPase activity assay. We have confirmed that Cu2+ acts as the oxidant in the reaction and the main chromogenic product of OPD is 2,3-diaminophenazine (usually called OPDox) in the assay by combining the ESI-MS, 1H NMR, and XPS spectra analysis. Direct electrochemical insights into the Cu2+-triggered and PPi-inhibited mechanism were performed by cyclic voltammetry characterizations of the Cu2+ in the absence and presence of PPi for the first time. Furthermore, the proposed analytical system with clear response mechanism exhibits a promising outlook for the PPase activity assay in real biological samples and inhibitor screening.

Highly selective and sensitive recognition of histidine based on the oxidase-like activity of Cu2+ ions

Xu, Yan,Wu, Xiao-Qiong,Shen, Jiang-Shan,Zhang, Hong-Wu

, p. 92114 - 92120 (2015)

Developing simple, highly sensitive and selective sensing systems for histidine (His) is important due to its biological significance. In this report, Cu2+ ions serving as the oxidase mimics towards O-phenylenediamine (OPD) were investigated in detail. Experimental results revealed that the oxidase-like activity of Cu2+ ions is substantially higher than that of Cu/CuO nanoparticles. On the basis of these findings, a simple, highly sensitive and selective PL sensing platform for His could be developed, with a limit of detection (LOD) as low as 0.33 μM. Furthermore, experiments of His recovery in human urine samples were successfully conducted by employing the established sensing system with satisfactory results.

A novel self-assembled supramolecular sensor based on thiophene-functionalized imidazophenazine for dual-channel detection of Ag+ in an aqueous solution

Shi, Hai-Xiong,Li, Wen-Ting,Li, Qiao,Zhang, Hai-Li,Zhang, You-Ming,Wei, Tai-Bao,Lin, Qi,Yao, Hong

, p. 53439 - 53444 (2017)

Herein, a novel self-assembled supramolecular sensor (S1) based on thiophene-functionalized imidazophenazine for Ag+ was designed and synthesized. It showed dual-channel detection properties for Ag+ based on the competitive mechanism of supramolecular self-assembly with high sensitivity and selectivity even in the presence of other metal ions. Its detection limit for Ag+ is 8.18 × 10-9 M. Upon the addition of Ag+, the solution changes from yellow to light purple and the fluorescence is quenched. Furthermore, the sensing mechanism between Ag+ and S1 is investigated via IR and 1H NMR spectroscopy, mass spectrometry, and density functional theory calculations.

High stability in organic solvent of heme proteins immobilized in the interlayers of magadiite nanoparticles

Peng, Shuge,Gao, Qiuming,Shi, Jianlin

, p. 1210 - 1211 (2004)

Enzymatic activities of heme proteins, myoglobin (Mb) and hemoglobin (Hb), immobilized in the interlayers of magadiite nanoparticles under mild condition, toward the oxidation of o-phenylenediamine (OPD) in an organic solvent were firstly reported. The immobilized heme proteins showed higher stability than that of free Mb and Hb in organic toluene solution.

Colorimetric and fluorescent dual-mode strategy for sensitive detection of sulfide: Target-induced horseradish peroxidase deactivation

Bao, Jie,Lu, Haifeng,Peng, Guoyu,Xu, Shuxin,Zhao, Lihua

, (2020)

Environmental pollution caused by sulfide compounds has become a major problem for public health. Hence, accurate detection of sulfide anions (S2?) level is valuable and vital for environmental monitoring and protection. Here, we report a new colorimetric/fluorescent dual-mode sensor for the determination of S2? based on the inhibition of enzyme activity and the unique optical properties of produced 2,3-diaminophenazine (DAP), thus making the analytical results more convincing. In this strategy, horseradish peroxidase (HRP) enzyme is used for catalyzing the H2O2-mediated oxidation of o-phenylenediamine (OPD) to produce DAP, and the color changed to bright yellow and produced orange yellow fluorescence. But the presence of S2? could cause the deactivation of HRP, which decreased the amount of DAP and consequently resulted in a substantial SPR band fading and an evident fluorescence quenching simultaneously. The mechanism of S2? sensor was examined by combining the UV–vis absorption spectra, fluorescence spectra and electrospray ionization mass spectrometry analysis. Under optimal conditions, the colorimetric and fluorescent linear responses of the proposed method exhibited a wide linear range from 2.5 nM–7.5 μM with ultralow detection limits of 1.2 nM and 0.9 nM, respectively. Some potential interferents (such as F?, Cl?, Br?, I?, SO4 2?, SO3 2?, SCN?, H2PO4 ?, HPO4 2?, Ac?, NO3 ?, CO3 2?) in real samples showed no interference. Moreover, the proposed method offered advantages of simple, low-cost instruments and rapid assay without the utilization of nanomaterials and has been successfully applied to determine S2? content in lake water samples with satisfying recoveries over 97.6%. More importantly, the present S2? sensor not only afforded a new optical sensing pattern for bioanalysis and environment monitoring, but also extends the application field of HRP-catalyzed OPD–H2O2 system.

Oxidation of o-phenylenediamine to 2,3-diaminophenazine in the presence of cubic ferrites MFe2O4 (M = Mn, Co, Ni, Zn) and the application in colorimetric detection of H2O2

Vetr, Fahime,Moradi-Shoeili, Zeinab,?zkar, Saim

, (2018)

Metal ferrites nanocrystallites, MFe2O4 (M?=?Mn, Co, Ni, Zn) were prepared by coprecipitation method and characterized by a combination of physico-chemical and spectroscopic techniques. MFe2O4 nanoparticles having particle size in the range 10–35?nm were tested as catalysts in the oxidation of o-phenylenediamine (OPD) to 2,3–diaminophenazine (DAP) using hydrogen peroxide as oxidant at room temperature. Kinetic data was collected for the catalytic oxidation of OPD to DAP by monitoring the UV–vis absorbance at 415?nm and fit well to the Michaelis–Menten model yielding kinetic parameters Km (Michaelis–Menten constant) and Vmax (maximum rate of reaction). MnFe2O4 nanoparticles provide the highest catalytic activity in the oxidation of OPD to DAP at room temperature. A colorimetric method was developed based on the MnFe2O4/OPD system for the detection of H2O2 in reaction solution. The method has a detection limit of 30 μM for H2O2 and wide linear range.

o-Phenylenediamine as a reaction-based probe for the fluorescent detection of Ce(IV) ions

Lai, Xiaojing,Ye, Qiuxiang,Wang, Ruixiang,Wang, Peng,Liu, Jin-Biao

, p. 28 - 33 (2021)

o-Phenylenediamine as a new fluorescent probe is designed for detecting Ce(IV) ions. The mechanism of detection relies on the oxidative activity of Ce(IV) ions, which can promote the oxidative cyclization of o-Phenylenediamine leading to the formation of fluorescent 2,3-diaminophenazine and giving a more than 150-fold fluorescence enhancement. Furthermore, the o-Phenylenediamine fluorescent probe was effectively used for the detection of Ce(IV) ions in river water, tap water, rainwater, and lateritic soil from Ganzhou.

Ratiometric fluorescent sensor based oxazolo-phenazine derivatives for detect hypochlorite via oxidation reaction and its application in environmental samples

Zhang, You-Ming,Fang, Hu,Zhu, Wei,He, Jun-Xia,Yao, Hong,Wei, Tai-Bao,Lin, Qi,Qu, Wen-Juan

, (2020)

In this work, we designed and synthesized a ratiometric fluorescent sensor (POC) based phenazine derivative which can specifically detect hypochlorite (detection limit equals to 8.9 × 10?7 M) in DMSO/H2O (3:7, v/v) solution. With addition of hypochlorite to the solution of POC, hypochlorite broken π-π stacking of POC, and then oxidizes sulfur atoms in phenazine groups to sulfoxide, which resulted in the fluorescent color changed from blue to yellow. Job's plot showed that binding stoichiometry of POC with ClO? was 2:1. In addition, POC could be used to real-time detect hypochlorite in environment samples, and the naked eyes detection limit reached up to 7 × 10?5 M.

A ratiometric fluorescence probe based on carbon dots for discriminative and highly sensitive detection of acetylcholinesterase and butyrylcholinesterase in human whole blood

Xu, Xiaoman,Cen, Yao,Xu, Guanhong,Wei, Fangdi,Shi, Menglan,Hu, Qin

, p. 232 - 236 (2019)

A ratiometric fluorescence probe based on carbon dots (CDs) was developed for discriminative and highly sensitive detection of acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) activity in human whole blood. When o-phenylenediamine (OPD) was oxidized by Cu2+, the product 2,3-diaminophenazine (oxOPD) could effectively quench the fluorescence of CDs at 460 nm due to the inner filter effect and gave rise to a new emission peak at 570 nm. The AChE or BChE catalyzed hydrolysis reaction of acetylthiocholine or butyrylthiocholine to generate thiocholine, whose sulfhydryl group strongly captured Cu2+ to inhibit the oxidization of OPD, thus effectively preserving the natural fluorescence emission of CDs. The resulting fluorescence intensity ratio served as the signal output of the probe for cholinesterases (ChEs) activity sensing. The activities of AChE and BChE were determined to range from 0.2 to 14.0 U L?1 and from 0.1 to 5.0 U L?1, with detection limits of 0.1 U L?1 and 0.04 U L?1, respectively. Additionally, the IC50 of tacrine and ethopropazine for the inhibition of AChE and BChE were estimated to be 29.8 nM and 132.6 nM, respectively. Moreover, the probe was successfully applied to the discriminative determination of AChE and BChE in human whole blood without any pretreatment. These results suggested that the proposed strategy provided a discriminative, sensitive and robust analytical platform for ChEs clinical diagnostics and drug screening.

A green approach to the synthesis of 2,3-diaminophenazine using a photocatalytic system of CdFe2O4/TiO2 nanoparticles

Ragab, Sherif S.,Badawy, Abdelrahman A.,El Nazer, Hossam A.

, p. 719 - 724 (2019)

In recent years, the development of novel green chemistry routes for the synthesis of organic compounds has become very attractive to many research groups. Nanoparticles have been widely used because of their potential applications in catalysis, environmental remediation, electronic fields, biomedical, and industrial fields. In this article, a rapid, efficient, and simple approach was applied for the synthesis of 2,3-diaminophenazine using a new photocatalytic system of CdFe2O4/TiO2 nanoparticles in water as a benign solvent. The structure of the synthesized CdFe2O4/TiO2 nanoparticle was confirmed using different methods such as transmission electron microscope (TEM), X-ray diffraction (XRD), and magnetic measurements. It was found that the rate and yield of the photocatalytic synthesis of 2,3-diaminophenazine were improved using CdFe2O4/TiO2 nanoparticles compared to other methods.

Universal Nanoplatform for Formaldehyde Detection Based on the Oxidase-Mimicking Activity of MnO2 Nanosheets and the in Situ Catalysis-Produced Fluorescence Species

Zhao, Qixia,Shen, Tong,Liu, Yujiao,Hu, Xiaojun,Zhao, Wenying,Ma, Zhangyan,Li, Peipei,Zhu, Xiaohua,Zhang, Youyu,Liu, Meiling,Yao, Shouzhuo

, p. 7303 - 7312 (2021)

Formaldehyde (HCHO) pollution is a scientific problem of general concern and has aroused wide attention. In this work, a fluorometric method for sensitive detection of formaldehyde was developed based on the oxidase-mimicking activity of MnO2 nanosheets in the presence of o-phenylenediamine (OPD). The MnO2 nanosheets were prepared by the bottom-up approach using manganese salt as the precursor, followed by the exfoliation with bovine serum albumin. The as-prepared MnO2 nanosheets displayed excellent oxidase-mimicking activity, and can be used as the nanoplatform for sensing in fluorometric analysis. OPD was used as a typical substrate because MnO2 nanosheets can catalyze the oxidation of OPD to generate yellow 2,3-diaminophenazine (DAP), which can emit bright yellow fluorescence at the wavelength of 560 nm. While in the presence of formaldehyde, the fluorescence was greatly quenched because formaldehyde can react with OPD to form Schiff bases that decreased the oxidation reaction of OPD to DAP. The main mechanism and the selectivity of the platform were studied. As a result, formaldehyde can be sensitively detected in a wide linear range of 0.8-100 μM with the detection limit as low as 6.2 × 10-8 M. The platform can be used for the detection of formaldehyde in air, beer, and various food samples with good performance. This work not only expands the application of MnO2 nanosheets in fluorescence sensing, but also provides a sensitive and selective method for the detection of formaldehyde in various samples via a new mechanism.

Copper(II) complexes as catalyst for the aerobic oxidation of o-phenylenediamine to 2,3-diaminophenazine

Khattar, Raghvi,Yadav, Anjana,Mathur, Pavan

, p. 375 - 381 (2015)

Two new mononuclear copper(II) complexes [Cu (L) (NO3)2] (1) and [Cu (L) Br2] (2) where (L = bis(1-(pyridin-2-ylmethyl)-benzimidazol-2-ylmethyl)ether) are synthesized and characterized by single-crystal X-ray diffraction analysis, elemental analysis, UV-Visible, IR spectroscopy, EPR and cyclic voltammetry. The complexes exhibit different coordination structures; the E1/2 value of the complex (1) is found to be relatively more cathodic than that of complex (2). X-band EPR spectra at low temperature in DMF supports a tetragonally distorted complex (1) while complex (2) shows three different g values suggesting a rhombic geometry. These complexes were utilized as a catalyst for the aerobic oxidation of o-phenylenediamine to 2,3-diaminophenazine assisted by molecular oxygen. The initial rate of reaction is dependent on the concentration of Cu(II) complex as well as substrate, and was found to be higher for the nitrate bound complex, while presence of acetate anion acts as a mild inhibitor of the reaction, as it is likely to pick up protons generated during the course of reaction. The inhibition suggests that the generated protons are further required in another important catalytic step.

Method for rapidly synthesizing 2, 3-diaminophenazine through ultrasonic radiation catalysis

-

Paragraph 0022-0029, (2021/07/17)

The invention provides a method for rapidly synthesizing 2, 3-diaminophenazine through ultrasonic radiation catalysis. The method specifically comprises the following steps: preparing an o-phenylenediamine raw material solution, preparing a catalyst transition metal salt solution, mixing the raw material solution and the transition metal salt solution, and carrying out ultrasonic radiation assisted reaction in an ultrasonic reactor, and washing and purifying the reaction product. According to the synthesis process, the target compound 2, 3-aminophenazine is rapidly and efficiently synthesized by adopting an ultrasonic radiation assisted reaction mode and taking a common low-valence chemical reagent o-phenylenediamine as the raw material, the whole process is environment-friendly and safe, and the reaction yield is relatively high so that the synthesis production cost of the 2, 3-aminophenazine is greatly reduced, and the application range of the 2, 3-aminophenazine is expanded.

TEMPO-catalyzed electrochemical dehydrogenative cyclocondensation of: O -aminophenols: Synthesis of aminophenoxazinones as antiproliferative agents

Cai, Yun-Rui,Ji, Su-Hui,Ma, Zhi-Yuan,Shonhe, Chantale,Zhou, Jianmin

supporting information, p. 8566 - 8570 (2021/11/17)

The aminophenoxazinone core is widely prevalent in natural products, dyes and pharmaceutical molecules. We report here a TEMPO-catalyzed electrosynthetic method allowing the dehydrogenative cyclocondensation of o-aminophenols. This mild and sustainable method proceeds in the absence of stoichiometric oxidants and uses an easily available organo-electrocatalyst to access pharmaceutically valuable 2-aminophenoxazinones. Mechanistic studies indicate that the electrochemically generated TEMPO+ enables the oxidative radical homo-dimerization of o-aminophenols. The application of electrosynthesis provides an approach for the synthesis of pseudo-aminophenoxazinone alkaloids with improved structural diversification and bioactivities. This journal is

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