Product Name

  • Name

    3-AMINO-PHENAZIN-2-OL

  • EINECS
  • CAS No. 4569-77-1
  • Article Data19
  • CAS DataBase
  • Density 1.46g/cm3
  • Solubility
  • Melting Point >300℃
  • Formula C12H9 N3 O
  • Boiling Point 381.6°Cat760mmHg
  • Molecular Weight 211.223
  • Flash Point 184.6°C
  • Transport Information
  • Appearance
  • Safety Mutation data reported. When heated to decomposition it emits toxic vapors of NOx.
  • Risk Codes
  • Molecular Structure Molecular Structure of 4569-77-1 (3-AMINO-PHENAZIN-2-OL)
  • Hazard Symbols
  • Synonyms 2-Amino-3-hydroxyphenazine;2-Hydroxy-3-aminophenazine; 3-Amino-2-hydroxyphenazine; 3-Amino-2-phenazinol;NSC 52575
  • PSA 72.03000
  • LogP 2.65200

Synthetic route

1,2-diamino-benzene
95-54-5

1,2-diamino-benzene

A

2,3-diaminephenazine
655-86-7

2,3-diaminephenazine

B

2-amino-3-hydroxy-phenazine
4569-77-1

2-amino-3-hydroxy-phenazine

Conditions
ConditionsYield
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

2-amino-5-hydroxy-[1,4]benzoquinone

o-phenylenediamine hydrochloride
39145-59-0

o-phenylenediamine hydrochloride

2-amino-3-hydroxy-phenazine
4569-77-1

2-amino-3-hydroxy-phenazine

Conditions
ConditionsYield
With ethanol
1,2-diamino-benzene
95-54-5

1,2-diamino-benzene

2-amino-3-hydroxy-phenazine
4569-77-1

2-amino-3-hydroxy-phenazine

Conditions
ConditionsYield
With hydrogenchloride; iron(III) chloride In water at 60 - 70℃;
2-amino-3-hydroxy-phenazine
4569-77-1

2-amino-3-hydroxy-phenazine

1,2-diamino-benzene
95-54-5

1,2-diamino-benzene

5,14-dihydro-5,7,12,14-tetraazapentacene
111076-33-6

5,14-dihydro-5,7,12,14-tetraazapentacene

Conditions
ConditionsYield
With hydrogenchloride; sodium chloride In water at 320℃; for 0.0833333h;100%
2-amino-3-hydroxy-phenazine
4569-77-1

2-amino-3-hydroxy-phenazine

C12H8N3O(1-)*Na(1+)

C12H8N3O(1-)*Na(1+)

Conditions
ConditionsYield
With sodium hydroxide In ethanol at 20℃;98%
2-amino-3-hydroxy-phenazine
4569-77-1

2-amino-3-hydroxy-phenazine

4,5-dimethyl-1,2-phenylenediamine
3171-45-7

4,5-dimethyl-1,2-phenylenediamine

8,9-dimethyl-5,14-dihydro-5,7,12,14-tetraazapentacene

8,9-dimethyl-5,14-dihydro-5,7,12,14-tetraazapentacene

Conditions
ConditionsYield
With hydrogenchloride; sodium chloride In water at 320℃; for 0.0833333h;95%
2-amino-3-hydroxy-phenazine
4569-77-1

2-amino-3-hydroxy-phenazine

2-Fluorobenzaldehyde
446-52-6

2-Fluorobenzaldehyde

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

ethyl 3,5-diamino-1-(2-fluorophenyl)-1H-pyrano[3,2-a]phenazine-2-carboxylate

ethyl 3,5-diamino-1-(2-fluorophenyl)-1H-pyrano[3,2-a]phenazine-2-carboxylate

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane In ethanol Reflux;93%
2-amino-3-hydroxy-phenazine
4569-77-1

2-amino-3-hydroxy-phenazine

2-chloro-benzaldehyde
89-98-5

2-chloro-benzaldehyde

malononitrile
109-77-3

malononitrile

3,5-diamino-1-(2-chlorophenyl)-1H-pyrano[3,2-a]phenazine-2-carbonitrile

3,5-diamino-1-(2-chlorophenyl)-1H-pyrano[3,2-a]phenazine-2-carbonitrile

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane In ethanol Reflux;91%
m-bromobenzoic aldehyde
3132-99-8

m-bromobenzoic aldehyde

2-amino-3-hydroxy-phenazine
4569-77-1

2-amino-3-hydroxy-phenazine

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

ethyl 3,5-diamino-1-(3-bromophenyl)-1H-pyrano[3,2-a]phenazine-2-carboxylate

ethyl 3,5-diamino-1-(3-bromophenyl)-1H-pyrano[3,2-a]phenazine-2-carboxylate

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane In ethanol Reflux;90%
2-amino-3-hydroxy-phenazine
4569-77-1

2-amino-3-hydroxy-phenazine

benzaldehyde
100-52-7

benzaldehyde

malononitrile
109-77-3

malononitrile

C22H15N5O

C22H15N5O

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane In ethanol Reflux; Inert atmosphere;89%
2-amino-3-hydroxy-phenazine
4569-77-1

2-amino-3-hydroxy-phenazine

4-bromo-3,5-dimethoxybenzaldehyde
31558-40-4

4-bromo-3,5-dimethoxybenzaldehyde

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

ethyl 3,5-diamino-1-(4-bromo-3,5-dimethoxyphenyl)-1H-pyrano[3,2-a]phenazine-2-carboxylate

ethyl 3,5-diamino-1-(4-bromo-3,5-dimethoxyphenyl)-1H-pyrano[3,2-a]phenazine-2-carboxylate

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane In ethanol Reflux;89%
2-amino-3-hydroxy-phenazine
4569-77-1

2-amino-3-hydroxy-phenazine

2,6-dichlorobenzaldehyde
83-38-5

2,6-dichlorobenzaldehyde

malononitrile
109-77-3

malononitrile

3,5-diamino-1-(2,6-dichlorophenyl)-1H-pyrano[3,2-a]phenazine-2-carbonitrile

3,5-diamino-1-(2,6-dichlorophenyl)-1H-pyrano[3,2-a]phenazine-2-carbonitrile

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane In ethanol Reflux;86%
2-amino-3-hydroxy-phenazine
4569-77-1

2-amino-3-hydroxy-phenazine

5-bromoveratralaldehyde
6948-30-7

5-bromoveratralaldehyde

malononitrile
109-77-3

malononitrile

3,5-diamino-1-(3-bromo-4,5-dimethoxyphenyl)-1H-pyrano[3,2-a]phenazine-2-carbonitrile

3,5-diamino-1-(3-bromo-4,5-dimethoxyphenyl)-1H-pyrano[3,2-a]phenazine-2-carbonitrile

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane In ethanol Reflux;86%
2-amino-3-hydroxy-phenazine
4569-77-1

2-amino-3-hydroxy-phenazine

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

ethyl 3,5-diamino-1-(2-bromophenyl)-1H-pyrano[3,2-a]phenazine-2-carboxylate

ethyl 3,5-diamino-1-(2-bromophenyl)-1H-pyrano[3,2-a]phenazine-2-carboxylate

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane In ethanol Reflux;86%
2-amino-3-hydroxy-phenazine
4569-77-1

2-amino-3-hydroxy-phenazine

5-bromo-2-methoxybenzaldehyde
25016-01-7

5-bromo-2-methoxybenzaldehyde

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

ethyl 3,5-diamino-1-(5-bromo-2-methoxyphenyl)-1H-pyrano[3,2-a]phenazine-2-carboxylate

ethyl 3,5-diamino-1-(5-bromo-2-methoxyphenyl)-1H-pyrano[3,2-a]phenazine-2-carboxylate

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane In ethanol Reflux;86%
carbon disulfide
75-15-0

carbon disulfide

2-amino-3-hydroxy-phenazine
4569-77-1

2-amino-3-hydroxy-phenazine

2-mercapto-oxazole[4,5-b]phenazine
92978-52-4

2-mercapto-oxazole[4,5-b]phenazine

Conditions
ConditionsYield
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

2-amino-3-hydroxy-phenazine

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

malononitrile
109-77-3

malononitrile

3,5-diamino-1-(4-bromophenyl)-1H-pyrano[3,2-a]phenazine-2-carbonitrile

3,5-diamino-1-(4-bromophenyl)-1H-pyrano[3,2-a]phenazine-2-carbonitrile

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane In ethanol Reflux;85%
2-amino-3-hydroxy-phenazine
4569-77-1

2-amino-3-hydroxy-phenazine

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

ethyl 3,5-diamino-1-(4-nitrophenyl)-1H-pyrano[3,2-a]phenazine-2-carboxylate

ethyl 3,5-diamino-1-(4-nitrophenyl)-1H-pyrano[3,2-a]phenazine-2-carboxylate

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane In ethanol Reflux;85%
2-amino-3-hydroxy-phenazine
4569-77-1

2-amino-3-hydroxy-phenazine

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

3,4-dichlorobenzaldehyde
6287-38-3

3,4-dichlorobenzaldehyde

ethyl 3,5-diamino-1-(3,4-dichlorophenyl)-1H-pyrano[3,2-a]phenazine-2-carboxylate

ethyl 3,5-diamino-1-(3,4-dichlorophenyl)-1H-pyrano[3,2-a]phenazine-2-carboxylate

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane In ethanol Reflux;85%
2-amino-3-hydroxy-phenazine
4569-77-1

2-amino-3-hydroxy-phenazine

5-bromoveratralaldehyde
6948-30-7

5-bromoveratralaldehyde

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

ethyl 3,5-diamino-1-(3-bromo-4,5-dimethoxyphenyl)-1H-pyrano[3,2-a]phenazine-2-carboxylate

ethyl 3,5-diamino-1-(3-bromo-4,5-dimethoxyphenyl)-1H-pyrano[3,2-a]phenazine-2-carboxylate

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane In ethanol Reflux;85%
2-amino-3-hydroxy-phenazine
4569-77-1

2-amino-3-hydroxy-phenazine

3-fluoro-p-anisaldehyde
351-54-2

3-fluoro-p-anisaldehyde

malononitrile
109-77-3

malononitrile

3,5-diamino-1-(3-fluoro-4-methoxyphenyl)-1H-pyrano[3,2-a]phenazine-2-carbonitrile

3,5-diamino-1-(3-fluoro-4-methoxyphenyl)-1H-pyrano[3,2-a]phenazine-2-carbonitrile

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane In ethanol Reflux;84%
2-amino-3-hydroxy-phenazine
4569-77-1

2-amino-3-hydroxy-phenazine

3-fluoro-p-anisaldehyde
351-54-2

3-fluoro-p-anisaldehyde

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

ethyl 3,5-diamino-1-(3-fluoro-4-methoxyphenyl)-1H-pyrano[3,2-a]phenazine-2-carboxylate

ethyl 3,5-diamino-1-(3-fluoro-4-methoxyphenyl)-1H-pyrano[3,2-a]phenazine-2-carboxylate

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane In ethanol Reflux;84%
2-amino-3-hydroxy-phenazine
4569-77-1

2-amino-3-hydroxy-phenazine

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

4-ethylbenzylaldehyde
4748-78-1

4-ethylbenzylaldehyde

ethyl 3,5-diamino-1-(4-ethylphenyl)-1H-pyrano[3,2-a]phenazine-2-carboxylate

ethyl 3,5-diamino-1-(4-ethylphenyl)-1H-pyrano[3,2-a]phenazine-2-carboxylate

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane In ethanol Reflux;83%
2-amino-3-hydroxy-phenazine
4569-77-1

2-amino-3-hydroxy-phenazine

2,6-dichlorobenzaldehyde
83-38-5

2,6-dichlorobenzaldehyde

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

ethyl 3,5-diamino-1-(2,6-dichlorophenyl)-1H-pyrano[3,2-a]phenazine-2-carboxylate

ethyl 3,5-diamino-1-(2,6-dichlorophenyl)-1H-pyrano[3,2-a]phenazine-2-carboxylate

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane In ethanol Reflux;83%
2-amino-3-hydroxy-phenazine
4569-77-1

2-amino-3-hydroxy-phenazine

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

malononitrile
109-77-3

malononitrile

3,5-diamino-1-(4-chlorophenyl)-1H-pyrano[3,2-a]phenazine-2-carbonitrile

3,5-diamino-1-(4-chlorophenyl)-1H-pyrano[3,2-a]phenazine-2-carbonitrile

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane In ethanol Reflux;82%
2-amino-3-hydroxy-phenazine
4569-77-1

2-amino-3-hydroxy-phenazine

(4-isopropylbenzaldehyde)
122-03-2

(4-isopropylbenzaldehyde)

malononitrile
109-77-3

malononitrile

3,5-diamino-1-(4-isopropylphenyl)-1H-pyrano[3,2-a]phenazine-2-carbonitrile

3,5-diamino-1-(4-isopropylphenyl)-1H-pyrano[3,2-a]phenazine-2-carbonitrile

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane In ethanol Reflux;82%
2-amino-3-hydroxy-phenazine
4569-77-1

2-amino-3-hydroxy-phenazine

malononitrile
109-77-3

malononitrile

syringic aldehyde
134-96-3

syringic aldehyde

3,5-diamino-1-(4-hydroxy-3,5-dimethoxyphenyl)-1H-pyrano[3,2-a]phenazine-2-carbonitrile

3,5-diamino-1-(4-hydroxy-3,5-dimethoxyphenyl)-1H-pyrano[3,2-a]phenazine-2-carbonitrile

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane In ethanol Reflux;82%
2-amino-3-hydroxy-phenazine
4569-77-1

2-amino-3-hydroxy-phenazine

4-bromo-3,5-dimethoxybenzaldehyde
31558-40-4

4-bromo-3,5-dimethoxybenzaldehyde

malononitrile
109-77-3

malononitrile

3,5-diamino-1-(4-bromo-3,5-dimethoxyphenyl)-1H-pyrano[3,2-a]phenazine-2-carbonitrile

3,5-diamino-1-(4-bromo-3,5-dimethoxyphenyl)-1H-pyrano[3,2-a]phenazine-2-carbonitrile

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane In ethanol Reflux;82%
2-amino-3-hydroxy-phenazine
4569-77-1

2-amino-3-hydroxy-phenazine

3-Chlorobenzaldehyde
587-04-2

3-Chlorobenzaldehyde

malononitrile
109-77-3

malononitrile

3,5-diamino-1-(3-chlorophenyl)-1H-pyrano[3,2-a]phenazine-2-carbonitrile

3,5-diamino-1-(3-chlorophenyl)-1H-pyrano[3,2-a]phenazine-2-carbonitrile

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane In ethanol Reflux;81%
2-amino-3-hydroxy-phenazine
4569-77-1

2-amino-3-hydroxy-phenazine

3,4-dichlorobenzaldehyde
6287-38-3

3,4-dichlorobenzaldehyde

malononitrile
109-77-3

malononitrile

3,5-diamino-1-(3,4-dichlorophenyl)-1H-pyrano[3,2-a]phenazine-2-carbonitrile

3,5-diamino-1-(3,4-dichlorophenyl)-1H-pyrano[3,2-a]phenazine-2-carbonitrile

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane In ethanol Reflux;81%
2-amino-3-hydroxy-phenazine
4569-77-1

2-amino-3-hydroxy-phenazine

3-nitro-benzaldehyde
99-61-6

3-nitro-benzaldehyde

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

ethyl 3,5-diamino-1-(3-nitrophenyl)-1H-pyrano[3,2-a]phenazine-2-carboxylate

ethyl 3,5-diamino-1-(3-nitrophenyl)-1H-pyrano[3,2-a]phenazine-2-carboxylate

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane In ethanol Reflux;81%
2-amino-3-hydroxy-phenazine
4569-77-1

2-amino-3-hydroxy-phenazine

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

ethyl 3,5-diamino-1-(4-bromophenyl)-1H-pyrano[3,2-a]phenazine-2-carboxylate

ethyl 3,5-diamino-1-(4-bromophenyl)-1H-pyrano[3,2-a]phenazine-2-carboxylate

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane In ethanol Reflux;81%
2-amino-3-hydroxy-phenazine
4569-77-1

2-amino-3-hydroxy-phenazine

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

malononitrile
109-77-3

malononitrile

3,5-diamino-1-(4-nitrophenyl)-1H-pyrano[3,2-a]phenazine-2-carbonitrile

3,5-diamino-1-(4-nitrophenyl)-1H-pyrano[3,2-a]phenazine-2-carbonitrile

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

2-Amino-3-hydroxyphenazine Chemical Properties

The IUPAC name of 2-Amino-3-hydroxyphenazine (CAS NO.4569-77-1): 3-Amino-10H-phenazin-2-one
Synonyms: 2-Amino-3-phenazinol ; 3-Amino-2-phenazino ; 3-Amino-2-Phenazinol 
CAS: 4569-77-1
Molecular Formula:C12H9N3
Molecular Structure:

Formula Weight: 211.22 g/mol
Index of Refraction: 1.758 
Density: 1.46 g/cm3 
Flash Point: 184.6 °C 
Boiling Point: 381.6 °C at 760 mmHg 

2-Amino-3-hydroxyphenazine Toxicity Data With Reference

The toxicity information of 2-Amino-3-hydroxyphenazine (CAS NO.4569-77-1):

1.    

mic-bac-sat 80 ng/plate

    MUREAV    Mutation Research. 321 (1994),43.

2-Amino-3-hydroxyphenazine Safety Profile

The Hazard Codes of 2-Amino-3-hydroxyphenazine (CAS NO.4569-77-1):IrritantXi
Mutation data reported. When heated to decomposition it emits toxic vapors of NOx.

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