4569-77-1

Usage

Uses

Used in Chemical Synthesis:
3-Amino-phenazin-2-ol is used as a key intermediate in the synthesis of various organic compounds, particularly those with phenazin-based structures. Its presence allows for the formation of complex molecules with diverse properties and potential applications.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 3-Amino-phenazin-2-ol is utilized as a building block for the development of new drugs and therapeutic agents. Its unique structure and functional groups enable the creation of novel compounds with potential medicinal properties.
Used in Preparation of Dihydroazobenzene Compounds:
3-Amino-phenazin-2-ol is specifically used in the preparation of dihydroazobenzene compounds containing an o-diaminophenazine structure. This is achieved through the reaction of diamino small molecules with o-aminophenazine compounds, resulting in the formation of dihydroazobenzene derivatives with potential applications in various fields, such as dyes, pigments, and other specialty chemicals.

InChI:InChI=1/C12H9N3O/c13-7-5-10-11(6-12(7)16)15-9-4-2-1-3-8(9)14-10/h1-6,15H,13H2

Synthetic route

1,2-diamino-benzene (95-54-5) → 2,3-diaminephenazine (655-86-7) + 2-amino-3-hydroxy-phenazine (4569-77-1)

Conditions	Yield
With hydrogenchloride; iron(III) chloride at 20℃;	A 78% B n/a
With hydrogenchloride; iron(III) chloride
With hydrogenchloride; iron(III) chloride at 20℃; under 760 Torr; Title compound not separated from byproducts;

2-amino-5-hydroxy-[1,4]benzoquinone (775347-31-4) + o-phenylenediamine hydrochloride (39145-59-0) → 2-amino-3-hydroxy-phenazine (4569-77-1)

Conditions	Yield
With ethanol

1,2-diamino-benzene (95-54-5) → 2-amino-3-hydroxy-phenazine (4569-77-1)

Conditions	Yield
With hydrogenchloride; iron(III) chloride In water at 60 - 70℃;

2-amino-3-hydroxy-phenazine (4569-77-1) + 1,2-diamino-benzene (95-54-5) → 5,14-dihydro-5,7,12,14-tetraazapentacene (111076-33-6)

Conditions	Yield
With hydrogenchloride; sodium chloride In water at 320℃; for 0.0833333h;	100%

2-amino-3-hydroxy-phenazine (4569-77-1) → C12H8N3O(1-)*Na(1+)

Conditions	Yield
With sodium hydroxide In ethanol at 20℃;	98%

2-amino-3-hydroxy-phenazine (4569-77-1) + 4,5-dimethyl-1,2-phenylenediamine (3171-45-7) → 8,9-dimethyl-5,14-dihydro-5,7,12,14-tetraazapentacene

Conditions	Yield
With hydrogenchloride; sodium chloride In water at 320℃; for 0.0833333h;	95%

2-amino-3-hydroxy-phenazine (4569-77-1) + 2-Fluorobenzaldehyde (446-52-6) + ethyl 2-cyanoacetate (105-56-6) → ethyl 3,5-diamino-1-(2-fluorophenyl)-1H-pyrano[3,2-a]phenazine-2-carboxylate

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In ethanol Reflux;	93%

2-amino-3-hydroxy-phenazine (4569-77-1) + 2-chloro-benzaldehyde (89-98-5) + malononitrile (109-77-3) → 3,5-diamino-1-(2-chlorophenyl)-1H-pyrano[3,2-a]phenazine-2-carbonitrile

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In ethanol Reflux;	91%

m-bromobenzoic aldehyde (3132-99-8) + 2-amino-3-hydroxy-phenazine (4569-77-1) + ethyl 2-cyanoacetate (105-56-6) → ethyl 3,5-diamino-1-(3-bromophenyl)-1H-pyrano[3,2-a]phenazine-2-carboxylate

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In ethanol Reflux;	90%

2-amino-3-hydroxy-phenazine (4569-77-1) + benzaldehyde (100-52-7) + malononitrile (109-77-3) → C22H15N5O

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In ethanol Reflux; Inert atmosphere;	89%

2-amino-3-hydroxy-phenazine (4569-77-1) + 4-bromo-3,5-dimethoxybenzaldehyde (31558-40-4) + ethyl 2-cyanoacetate (105-56-6) → ethyl 3,5-diamino-1-(4-bromo-3,5-dimethoxyphenyl)-1H-pyrano[3,2-a]phenazine-2-carboxylate

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In ethanol Reflux;	89%

2-amino-3-hydroxy-phenazine (4569-77-1) + 2,6-dichlorobenzaldehyde (83-38-5) + malononitrile (109-77-3) → 3,5-diamino-1-(2,6-dichlorophenyl)-1H-pyrano[3,2-a]phenazine-2-carbonitrile

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In ethanol Reflux;	86%

2-amino-3-hydroxy-phenazine (4569-77-1) + 5-bromoveratralaldehyde (6948-30-7) + malononitrile (109-77-3) → 3,5-diamino-1-(3-bromo-4,5-dimethoxyphenyl)-1H-pyrano[3,2-a]phenazine-2-carbonitrile

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In ethanol Reflux;	86%

2-amino-3-hydroxy-phenazine (4569-77-1) + ethyl 2-cyanoacetate (105-56-6) + ortho-bromobenzaldehyde (6630-33-7) → ethyl 3,5-diamino-1-(2-bromophenyl)-1H-pyrano[3,2-a]phenazine-2-carboxylate

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In ethanol Reflux;	86%

2-amino-3-hydroxy-phenazine (4569-77-1) + 5-bromo-2-methoxybenzaldehyde (25016-01-7) + ethyl 2-cyanoacetate (105-56-6) → ethyl 3,5-diamino-1-(5-bromo-2-methoxyphenyl)-1H-pyrano[3,2-a]phenazine-2-carboxylate

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In ethanol Reflux;	86%

carbon disulfide (75-15-0) + 2-amino-3-hydroxy-phenazine (4569-77-1) → 2-mercapto-oxazole[4,5-b]phenazine (92978-52-4)

Conditions	Yield
With potassium hydroxide In ethanol; water for 26h; Heating;	85%
Stage #1: 2-amino-3-hydroxy-phenazine With potassium hydroxide In ethanol; water Heating; Stage #2: carbon disulfide In ethanol; water at 20℃;	60%
With potassium hydroxide In ethanol; water
With potassium hydroxide
With potassium hydroxide In ethanol; water at 80℃; for 26h;

2-amino-3-hydroxy-phenazine (4569-77-1) + 4-bromo-benzaldehyde (1122-91-4) + malononitrile (109-77-3) → 3,5-diamino-1-(4-bromophenyl)-1H-pyrano[3,2-a]phenazine-2-carbonitrile

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In ethanol Reflux;	85%

2-amino-3-hydroxy-phenazine (4569-77-1) + 4-nitrobenzaldehdye (555-16-8) + ethyl 2-cyanoacetate (105-56-6) → ethyl 3,5-diamino-1-(4-nitrophenyl)-1H-pyrano[3,2-a]phenazine-2-carboxylate

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In ethanol Reflux;	85%

2-amino-3-hydroxy-phenazine (4569-77-1) + ethyl 2-cyanoacetate (105-56-6) + 3,4-dichlorobenzaldehyde (6287-38-3) → ethyl 3,5-diamino-1-(3,4-dichlorophenyl)-1H-pyrano[3,2-a]phenazine-2-carboxylate

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In ethanol Reflux;	85%

2-amino-3-hydroxy-phenazine (4569-77-1) + 5-bromoveratralaldehyde (6948-30-7) + ethyl 2-cyanoacetate (105-56-6) → ethyl 3,5-diamino-1-(3-bromo-4,5-dimethoxyphenyl)-1H-pyrano[3,2-a]phenazine-2-carboxylate

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In ethanol Reflux;	85%

2-amino-3-hydroxy-phenazine (4569-77-1) + 3-fluoro-p-anisaldehyde (351-54-2) + malononitrile (109-77-3) → 3,5-diamino-1-(3-fluoro-4-methoxyphenyl)-1H-pyrano[3,2-a]phenazine-2-carbonitrile

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In ethanol Reflux;	84%

2-amino-3-hydroxy-phenazine (4569-77-1) + 3-fluoro-p-anisaldehyde (351-54-2) + ethyl 2-cyanoacetate (105-56-6) → ethyl 3,5-diamino-1-(3-fluoro-4-methoxyphenyl)-1H-pyrano[3,2-a]phenazine-2-carboxylate

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In ethanol Reflux;	84%

2-amino-3-hydroxy-phenazine (4569-77-1) + ethyl 2-cyanoacetate (105-56-6) + 4-ethylbenzylaldehyde (4748-78-1) → ethyl 3,5-diamino-1-(4-ethylphenyl)-1H-pyrano[3,2-a]phenazine-2-carboxylate

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In ethanol Reflux;	83%

2-amino-3-hydroxy-phenazine (4569-77-1) + 2,6-dichlorobenzaldehyde (83-38-5) + ethyl 2-cyanoacetate (105-56-6) → ethyl 3,5-diamino-1-(2,6-dichlorophenyl)-1H-pyrano[3,2-a]phenazine-2-carboxylate

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In ethanol Reflux;	83%

2-amino-3-hydroxy-phenazine (4569-77-1) + 4-chlorobenzaldehyde (104-88-1) + malononitrile (109-77-3) → 3,5-diamino-1-(4-chlorophenyl)-1H-pyrano[3,2-a]phenazine-2-carbonitrile

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In ethanol Reflux;	82%

2-amino-3-hydroxy-phenazine (4569-77-1) + (4-isopropylbenzaldehyde) (122-03-2) + malononitrile (109-77-3) → 3,5-diamino-1-(4-isopropylphenyl)-1H-pyrano[3,2-a]phenazine-2-carbonitrile

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In ethanol Reflux;	82%

2-amino-3-hydroxy-phenazine (4569-77-1) + malononitrile (109-77-3) + syringic aldehyde (134-96-3) → 3,5-diamino-1-(4-hydroxy-3,5-dimethoxyphenyl)-1H-pyrano[3,2-a]phenazine-2-carbonitrile

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In ethanol Reflux;	82%

2-amino-3-hydroxy-phenazine (4569-77-1) + 4-bromo-3,5-dimethoxybenzaldehyde (31558-40-4) + malononitrile (109-77-3) → 3,5-diamino-1-(4-bromo-3,5-dimethoxyphenyl)-1H-pyrano[3,2-a]phenazine-2-carbonitrile

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In ethanol Reflux;	82%

2-amino-3-hydroxy-phenazine (4569-77-1) + 3-Chlorobenzaldehyde (587-04-2) + malononitrile (109-77-3) → 3,5-diamino-1-(3-chlorophenyl)-1H-pyrano[3,2-a]phenazine-2-carbonitrile

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In ethanol Reflux;	81%

2-amino-3-hydroxy-phenazine (4569-77-1) + 3,4-dichlorobenzaldehyde (6287-38-3) + malononitrile (109-77-3) → 3,5-diamino-1-(3,4-dichlorophenyl)-1H-pyrano[3,2-a]phenazine-2-carbonitrile

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In ethanol Reflux;	81%

2-amino-3-hydroxy-phenazine (4569-77-1) + 3-nitro-benzaldehyde (99-61-6) + ethyl 2-cyanoacetate (105-56-6) → ethyl 3,5-diamino-1-(3-nitrophenyl)-1H-pyrano[3,2-a]phenazine-2-carboxylate

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In ethanol Reflux;	81%

2-amino-3-hydroxy-phenazine (4569-77-1) + 4-bromo-benzaldehyde (1122-91-4) + ethyl 2-cyanoacetate (105-56-6) → ethyl 3,5-diamino-1-(4-bromophenyl)-1H-pyrano[3,2-a]phenazine-2-carboxylate

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In ethanol Reflux;	81%

2-amino-3-hydroxy-phenazine (4569-77-1) + 4-nitrobenzaldehdye (555-16-8) + malononitrile (109-77-3) → 3,5-diamino-1-(4-nitrophenyl)-1H-pyrano[3,2-a]phenazine-2-carbonitrile

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In ethanol Reflux;	80%

Upstream product

• 95-54-5 1,2-diamino-benzene 
• 775347-31-4 2-amino-5-hydroxy-[1,4]benzoquinone 
• 39145-59-0 o-phenylenediamine hydrochloride 

Downstream Products

• 43193-60-8 pyrazine-2,3,5,6-tetracarboxylic acid 

Relevant academic research and scientific papers

Mercaptooxazole-phenazine based blue fluorescent sensor for the ultra-sensitive detection of mercury(II) ions in aqueous solution

Herein, a mercury(ii) ion fluorescent sensor (Z-3) with high sensitivity and immediate response is designed and synthesized. The sensor uses the phenazine group as a luminophore and sulfhydryl as a recognition moiety. The sensor is easily synthesized and it exhibits a remarkable blue shift with Hg2+. Correspondingly, its fluorescence color changes from yellow to blue. In addition, the low naked eye detection limit (10-5) of the sensor allows the identification of concentration limits. Moreover, the sensor could detect mercury(ii) ions over a wide pH range (from 2 to 8), which indicates that the detection can be carried out in aqueous systems. In addition, test strips are fabricated, which could act as a convenient pathway for the recognition of Hg2+.

Highly selective and sensitive chemosensor based on 2,3-diaminophenazine hydrochloride for the detection of cyanide in pure water and its application in plant seed samples

In this study, we prepared an efficient chemosensor based on 2,3-diaminophenazine hydrochloride, and it exhibited good dissolvability in water; more importantly, it could act as an efficient chemodosimeter for the selective detection of CN- in pure water. Upon reacting with CN-, 2,3-diaminophenazine hydrochloride (Q1) displayed a remarkable visible and fluorescence response simultaneously with significant changes in both absorption and fluorescence spectra. Furthermore, the absorption and fluorescence detection limits of CN- were 1.95 × 10-7 M and 1.13 × 10-9 M, respectively. For practical applications, test strips based on this chemosensor could serve as convenient CN- detection tools. The chemosensor was also successfully applied to the detection of CN- in plant seeds and several natural water samples.

A self-assembled supramolecular gel constructed by phenazine derivative and its application in ultrasensitive detection of cyanide

In this work, we constructed a supramolecular gel (PN-G) by phenazine derivative, which can ultrasensitive detect cyanide (detection limit equals to 4.18 × 10?10 M). The decrease of fluorescent intensity displayed a linear relationship in the range of 0–0.4 equivalents of cyanide. And no significant fluorescence quenching was observed for all used interfering ions. The cyanide recognition mechanism of PN-G was verified by XRD, NMR, MS and SEM. With addition of cyanide to the supramolecular gel (PN-G), cyanide broken π-π stacking of PN-G, and then PN-G undergoes a nucleophilic addition reaction with CN?, resulting in fluorescence quenched.

A simple water-soluble phenazine dye for colorimetric/ fluorogenic dual-mode detection and removal of Cu2+ in natural water and plant samples

Detection and removal of heavy metal ions in a variety of complex water systems using dyes remains a challenge. Here we have developed a rapid, low-cost, on-site water-soluble dye for the colorimetric/fluorogenic detection and removal of copper ions in natural water and plant samples. By comparing with dye molecule AHP, this water-soluble phenazine dye (AHPN) has a high fluorescence quantum yield and excellent coordinated ability with copper ions. AHPN can effectively remove copper ions in various natural water samples due to its strong binding ability with Cu2+. Moreover, the test strips also were fabricated and successfully used for real-time detection of Cu2+ in water with simple-to-use, low-cost, quick response and provide an obvious effect by naked-eye. All data in this experiment showed that this water-soluble phenazine dye AHPN has excellent effect on the detection and removal of Cu2+.

Recognition of dihydrogen phosphate ions using the cadmium complex of 2-pyridine-1H-imidazo[4,5-b]phenazine: Utilization of the mechanism of twisted intramolecular charge transfer, long wavelength emission

A long wavelength emission fluorescent and colorimetric chemosensor with high selectivity for H2PO4- ions was designed and synthesized according to the twisted intramolecular charge transfer (TICT) mechanism. The sensor bears a 2-pyridine-1H-imidazo[4,5-b]phenazine and Cd 2+ metal complex, which showed brilliant fluorescent and colorimetric response for H2PO4- anions in aqueous solution. The detection limit of the sensor towards H2PO 4- is 2.8 × 10-6 M, and other anions, including F-, Cl-, Br-, I-, AcO -, HSO4-, ClO4- and CN-, had nearly no influence on the probing behavior. The test strips based on the 2-pyridine-1H-imidazo[4,5-b]phenazine and Cd2+ metal complex (S2-Cd) were fabricated, which could act as convenient and efficient H2PO4- test kits.

Tailoring an HSO4-anion hybrid receptor based on a phenazine derivative

A catechol-functionalized phenazine imidazole (PD) was tailored with 2,3-diaminophenazine and 3,4-dihydroxy benzaldehyde, and it served as a hybrid acceptor for capturing HSO4- anions. The selectivity and sensitivity of the PD receptor for anion sensing were studied. It was found that the PD receptor could not only display a preferable sensitivity to HSO4- ions with a "turn-off"fluorescence response, but also have a strong anti-interference ability toward other common anions, especially basic anions such as CH3COO-, HPO42-, and H2PO4-. The anion recognition mechanism of PD towards HSO4- is based on multiple hydrogen bond interactions. Finally, the strips for anion detection were prepared, which were verified to be a convenient and high-efficiency test kit for detecting HSO4- ions with the naked eye.

Water-soluble phenazine derivative as well as preparation method and application thereof

The invention relates to a water-soluble phenazine derivative as well as a preparation method and an application thereof. The structural formula of the derivative is shown in the specification. The preparation method of the water-soluble phenazine derivative comprises the following steps: adding N, N-dimethylformamide, 2, 3-diaminophenazine, glacial acetic acid and 3, 4-dihydroxy benzaldehyde intoa reactor to obtain the phenazine derivative; in absolute ethyl alcohol, adding phenazine derivatives and sodium hydroxide into the absolute ethyl alcohol, and carrying out a stirring reaction at room temperature to obtain the water-soluble phenazine derivatives. The water-soluble phenazine derivative is used for anion recognition of a silicate ion sensor.

Mercury ion fluorescent sensor molecule, and synthesis and application thereof

The invention relates to sensor molecule, 2-sulfydryl-oxazole [4, 5-b] phenazine, capable of performing fluorescence detection on mercury ion. The sensor molecule is prepared through the following steps: taking ethyl alcohol and water as a solvent, KOH as a catalyst and 2-sulfydryl-3-aminophenazine and carbon disulfide as substrates, so as to perform reflux reaction; performing hot suction filtration after reaction, filtering filter liquor after the filter liquor is acidized, performing vacuum drying, and performing DMF recrystallization, so as to obtain yellow green solid namely the mercury ion sensor molecule. The sensor molecule meets Hg2+ in a water-bearing system, hydrogen ion is removed from sulfydryl firstly, then sulfydryl is coordinated with mercury ion, fluorescence becomes lightblue from yellow, and a new emission peak appears in a 492nm position. In addition, mercury ion is added at a room temperature, the fluorescence of solution can rapidly become light blue (smaller than 3 seconds), and a good naked eye identification effect can be achieved. Hg2+ test paper manufactured through the sensor molecule can further conveniently and rapidly detect mercury ion in an environment system.

Sensor molecule for identifying cyanide ions through colorimetric channel and fluorescent channel as well as preparation and application of sensor molecule

The invention designs and synthesizes a sensor molecule 2-phenyl-1H-imidazole [4, 5-b] phenazine capable of detecting cyanide ions through a colorimetric channel and a fluorescent channel. According to the sensor molecule, firstly, a dimer is formed by an intermolecular hydrogen bond, and then, a supramolecular self-assembly system is formed between phenazine rings according to pi-pi stacking, sothat a host molecule solution is enabled to give out strong fluorescence; after CN- is added, a host has the proton removal action, so that the self-assembly system is crashed to cause fluorescence quenching, the CN- can be identified with high selectivity in a water-bearing medium, and the identification process is not interfered by other negative ions. Additionally, after the CN- is added at room temperature, the fluorescence intensity of the solution is quickly weakened (less than 3s), and the solution becomes jacinth, so that a good naked eye identification effect can be achieved. According to CN-test paper made by adopting the sensor molecule, the cyanide ions in an environmental system can be detected conveniently and fast.

Sensor molecule for recognizing mercury ions with colorimetric fluorometric dual channel as well as synthesis and application thereof

The invention designs and synthesizes a sensor molecular for recognizing mercury ions with colorimetric fluorometric dual channel, namely 2-cyanomethyl-imidazole[4,5-b]phenazine. The sensor molecule is obtained by adopting normal butanol as a solvent and 2,3-diaminophenazine and ethyl cyanoacetate as a substrate to perform reflux reaction, performing the suction filter after the reaction and vacuum drying. When cation solutions are respectively added into a sensor molecular DMSO-H20 solution, the color of the solution immediately turns light only when Hg is added, the strong yellow fluorescence is completely quenched, so that the sensor molecule can specifically and selectively recognize Hg by virtue of fluorescence in an aqueous solution, the recognition process is not interfered with other cations. In addition, when the mercury ions are added under the room temperature, the fluorescence strength of the solution can be rapidly weakened (less than 3 seconds), and a good naked-eye recognition effect can be achieved. Hg test paper produced by using the sensor molecule can conveniently and rapidly detect the mercury ions in an environmental system.