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2,3-Diaminophenazine is a chemical compound characterized by its yellow to light brown needle-like crystals. It appears as brown to yellow needles and upon heating, it sublimes to form yellow leaflets with a melting point of 264°. It is soluble in alcohol and benzene, and when heated with zinc dust, it yields 2-aminophenazine and small amounts of phenazine.

655-86-7

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655-86-7 Usage

Uses

Used in Medical Research:
2,3-Diaminophenazine is used as a reagent for the study on detection of HIV-1 p24 antigen in patients with varying degrees of viremia using ELISA with photochemical signal amplification system.
Used in Environmental Analysis:
2,3-Diaminophenazine is used as a detection agent for heavy metals such as bismuth, cadmium, lead, copper, and mercury, playing a crucial role in environmental monitoring and analysis.

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 academic research and scientific papers

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).

Highly sensitive SERS sensor for mercury ions based on the catalytic reaction of mercury ion decorated Ag nanoparticles

Qi, Guohua,Fu, Cuicui,Chen, Gang,Xu, Shuping,Xu, Weiqing

, p. 49759 - 49764 (2015)

A surface-enhanced Raman scattering (SERS) sensor of mercury ions based on the coordinated catalytic reaction of Hg2+-Ag nanoparticles (NPs) has been designed and constructed for water quality monitoring. We combined Ag NPs (average particle size is 49 nm) with mercury ions to form Hg2+-Ag NPs in aqueous phase by electrostatic interactions. The formed Hg2+-Ag particles can catalyze a redox reaction between o-phenylendiamine (OPD) and dissolved oxygen to form 2,3-diaminephenazine (DAP), which is Raman-active and possesses a strong SERS signal due to the adherence to Ag NPs. Therefore we can trace the SERS intensity of DAP to determine mercury ions and the lowest detectable concentration of mercury is 1.0 nM using this method. This sensor displays higher sensitivity and selectivity and it possesses a certain value in terms of water quality detection.

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.

Thermal responsive microgels as recyclable carriers to immobilize active proteins with enhanced nonaqueous biocatalytic performance

Wu, Qing,Su, Teng,Mao, Yanjie,Wang, Qigang

, p. 11299 - 11301 (2013)

We describe the preparation of a thermoresponsive microgel, which can non-covalently immobilize active proteins with enhanced biocatalytic performance in organic solvents and easy reusability due to the porous microstructure and temperature responsive property.

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.

A Phenazine based colorimetric and fluorescent chemosensor for sequential detection of Ag+ and I? in aqueous media

Dongare, Pravin R.,Gore, Anil H.,Kolekar, Govind B.,Ajalkar, Balu D.

, p. 231 - 242 (2020)

A new colorimetric and fluorescent probe MNTPZ based on 1H-imidazo[4,5-b]phenazine derivative has been designed and synthesized for successive detection of Ag+ and I?. The probe MNTPZ shows selective colorimetric response by a change in color from yellow to orange and “turn-off” fluorometric response upon binding with Ag+ in DMSO: Water (pH = 7, 1:1, v/v) over other cations. The binding mode of probe MNTPZ to Ag+ was studied by Job's plot, 1H NMR studies, FT-IR spectroscopy and DFT calculations. Moreover, the situ generated probe MNTPZ+ Ag+ complex acted as an efficient fluorometric “turn-on” probe for I? via Ag+ displacement approach. The detection limit of probe MNTPZ for Ag+ and the resultant complex probe MNTPZ+ Ag+ for I? were determined to be 1.36 μmol/L and 1.03 μmol/L respectively. Notably, the developed probe was successfully used for quantitative determination of I? in real samples with satisfactory results.

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.

Au-Ag and Pt-Ag bimetallic nanoparticles@halloysite nanotubes: Morphological modulation, improvement of thermal stability and catalytic performance

Li, Siyu,Tang, Feng,Wang, Huixin,Feng, Junran,Jin, Zhaoxia

, p. 10237 - 10245 (2018)

In this study, Au-Ag and Pt-Ag bimetallic nanocages were loaded on natural halloysite nanotubes (HNTs) via galvanic exchange based on Ag@HNT. By changing the ratio of Au to Ag or Pt to Ag in exchange processes, Au-Ag@HNT and Pt-Ag@HNT with different nanostructures were generated. Both Au-Ag@HNT and Pt-Ag@HNT systems showed significantly improved efficiency as peroxidase-like catalysts in the oxidation of o-phenylenediamine compared with monometallic Au@HNT and Pt@HNT, although inert Ag is dominant in the composition of both Au-Ag and Pt-Ag nanocages. On the other hand, loading on HNTs enhanced the thermal stability for every system, whether monometallic Ag nanoparticles, bimetallic Au-Ag or Pt-Ag nanocages. Ag@HNT sustained thermal treatment at 400 °C in nitrogen with improved catalytic performance, while Au-Ag@HNT and Pt-Ag@HNT maintained or even had slightly enhanced catalytic efficiency after thermal treatment at 200 °C in nitrogen. This study demonstrated that natural halloysite nanotubes are a good support for various metallic nanoparticles, improving their catalytic efficiency and thermal stability.

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.

Cu MOF-based catalytic sensing for formaldehyde

Gao, Ping,Sun, Xiang-Ying,Liu, Bin,Lian, Hui-Ting,Liu, Xin-Qiang,Shen, Jiang-Shan

, p. 8105 - 8114 (2018)

Developing a catalyst with a uniform and well-defined crystal structure is very important to establish a catalytic sensing system with high efficiency. In this work, Cu-BTC metal-organic frameworks (MOFs) without a crystalline CuO or Cu2O phase were successfully synthesized by using a low temperature synthesis method, and the as-prepared Cu-BTC MOFs were found to have outstanding catalytic activity towards the traditional oxidase substrate, o-phenylenediamine (OPD), to generate a colored and fluorescent product. The results of the kinetics analysis revealed that the catalytic behavior of Cu-BTC MOFs towards OPD could well follow the typical Michaelis-Menten equation, indicative of a strong affinity between Cu-BTC MOFs and OPD. On the basis of these findings, taken together the condensation reaction between the -CHO group of formaldehyde and the -NH2 group of OPD to form Schiff base compounds, a novel Cu-BTC MOF-based catalytic sensing system for detecting gaseous formaldehyde could be successfully established.

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