4569-77-1

Basic information

• Product Name: 3-AMINO-PHENAZIN-2-OL
• Synonyms: 3-amino-2-Phenazinol;3-AMINO-PHENAZIN-2-OL;2-AMINO-3-HYDROXYPHENAZINE;3-amino-10H-phenazin-2-one;3-azanyl-10H-phenazin-2-one;2-Hydroxy-3-aminophenazine;3-Amino-2-hydroxyphenazine;NSC 52575
• CAS NO: 4569-77-1
• Molecular Formula: C₁₂H₉N₃O
• Molecular Weight: 211.22
• Mol File: 4569-77-1.mol
• Article Data: 15

Chemical Properties

• Melting Point: >300℃
• Boiling Point: 473℃
• Flash Point: 240℃
• Appearance: /
• Density: 1.458
• Vapor Pressure: 5.02E-06mmHg at 25°C
• Refractive Index: 1.5700 (estimate)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 7.15±0.30(Predicted)
• CAS DataBase Reference: 3-AMINO-PHENAZIN-2-OL(CAS DataBase Reference)
• NIST Chemistry Reference: 3-AMINO-PHENAZIN-2-OL(4569-77-1)
• EPA Substance Registry System: 3-AMINO-PHENAZIN-2-OL(4569-77-1)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 4569-77-1(Hazardous Substances Data)

Usage

Chemical Properties

Yellow crystals

Uses

3-Amino-phenazin-2-ol is used in preparation of dihydroazobenzene compound containing o-diaminophenazine structure from diamino small molecule and o-aminophenazine compound.

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 articles and documents

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+.

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.

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.

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.