4569-86-2

Basic information

• Product Name: CI 50206
• Synonyms: 3-Amino-7-(diethylamino)-5-phenyl phenazinium chloride, 3-Amino-7-(diethylamino)-5-phenylphenazinium chloride, N,N-Diethylphenosafranine;Methylene violet 3rax, pure;2-Amino-8-(diethylamino)-10-phenylphenazine-10-ium·chloride;PhenaziniuM,3-aMino-7-(diethylaMino)-5-phenyl-, chloride (1:1);N,N-DIETHYLPHENOSAFRANINE;Phenazinium,3-amino-7-(diethylamino)-5-phenyl-,chloride;3-AMINO-7-DIETHYLAMINO-5-PHENYL-PHENAZIN-5-IUM CHLORIDE;3-AMINO-7-(DIETHYLAMINO)-5-PHENYL-PHENAZINIUM CHLORIDE
• CAS NO: 4569-86-2
• Molecular Formula: C₂₂H₂₃N₄*Cl
• Molecular Weight: 378.9
• EINECS: 610-268-6
• Mol File: 4569-86-2.mol
• Article Data: 2

Chemical Properties

• Melting Point: 285 °C (dec.)(lit.)
• Appearance: dark green crystalline powder
• Storage Temp.: room temp
• CAS DataBase Reference: CI 50206(CAS DataBase Reference)
• NIST Chemistry Reference: CI 50206(4569-86-2)
• EPA Substance Registry System: CI 50206(4569-86-2)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 4569-86-2(Hazardous Substances Data)

Usage

Chemical Properties

dark green crystalline powder

Uses

Different sources of media describe the Uses of 4569-86-2 differently. You can refer to the following data:
1. Methylene Violet 3RAX is used in preparation of methylene violet derivatives as fluorescent probes for sulfide ion detection.
2. Methylene Violet 3RAX has been used as a reagent in a preparation of citrate methylene violet, which is used for staining yeast cells. It is also used as an internal standard in tandem mass spectrometry (MS/MS) for the quantification of methylene blue in blood samples.

General Description

Methylene violet 3RAX [MV3RAX, 3-amino-7-(diethylamino)-5-phenyl phenazinium chloride] is a phenazinium dye and is cationic in nature. It has several applications in staining chemistry. Methylene violet 3RAX dye has an antimalarial property. It is used as a probe for investigating guest–host interactions in dendrimers and this may have relevance in drug–DNA interactions.

InChI:InChI=1/C22H22N4.ClH/c1-3-25(4-2)18-11-13-20-22(15-18)26(17-8-6-5-7-9-17)21-14-16(23)10-12-19(21)24-20;/h5-15,23H,3-4H2,1-2H3;1H

Synthetic route

aniline (62-53-3) + N,N-diethylaniline (93-05-0) → 3-amino-7-(diethylamino)-5-phenylphenazinium chloride (4569-86-2)

Conditions	Yield
With hydrogenchloride; potassium dichromate; sodium acetate; acetic acid In water at 105℃; for 3h; Inert atmosphere; Darkness;	35%
With hydrogenchloride; potassium dichromate In aq. acetate buffer at 105℃; for 3h;	35%

3-amino-7-(diethylamino)-5-phenylphenazinium chloride (4569-86-2) + 4-(10,15,20-triphenyl-21H,23H-porphin-5-yl)benzoic acid → C67H51N8O(1+)*Cl(1-)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In chloroform at 60℃; for 10h;	85%

3-amino-7-(diethylamino)-5-phenylphenazinium chloride (4569-86-2) + [1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid (53-86-1) → C41H37ClN5O3(1+)*Cl(1-)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In chloroform at 60℃; for 12h;	80%

3-amino-7-(diethylamino)-5-phenylphenazinium chloride (4569-86-2) + p-toluenesulfonyl chloride (98-59-9) → 3-(4-methylbenzenesulfonamido)-7-(diethylamino)-5-phenylphenazinium chloride

Conditions	Yield
With triethylamine In chloroform at 60℃; for 2h;	78%

3-amino-7-(diethylamino)-5-phenylphenazinium chloride (4569-86-2) → 3-bromo-7-N,N-diethylamino-5-phenyl-phenazinium bromide

Conditions	Yield
With hydrogen bromide; sodium nitrite In water at 50℃; for 2h;	67%

N-(2-azidoethyl)-N-methylaniline (1249429-26-2) + 3-amino-7-(diethylamino)-5-phenylphenazinium chloride (4569-86-2) + trifluoroacetic acid (76-05-1) → C31H32N9(1+)*C2F3O2(1-) (1432151-27-3)

Conditions	Yield
Stage #1: 3-amino-7-(diethylamino)-5-phenylphenazinium chloride With nitrosonium tetrafluoroborate In acetonitrile at 0℃; for 0.25h; Stage #2: N-(2-azidoethyl)-N-methylaniline In acetonitrile at 0℃; for 1h; Stage #3: trifluoroacetic acid	64%

N-methyl-N-(pent-4-ynyl)aniline (1432151-88-6) + 3-amino-7-(diethylamino)-5-phenylphenazinium chloride (4569-86-2) + trifluoroacetic acid (76-05-1) → C34H35N6(1+)*C2F3O2(1-) (1432152-01-6)

Conditions	Yield
Stage #1: 3-amino-7-(diethylamino)-5-phenylphenazinium chloride With nitrosonium tetrafluoroborate In acetonitrile at 0℃; for 0.25h; Stage #2: N-methyl-N-(pent-4-ynyl)aniline In acetonitrile at 0℃; for 1h; Stage #3: trifluoroacetic acid	60%

phthalic anhydride (85-44-9) + 3-amino-7-(diethylamino)-5-phenylphenazinium chloride (4569-86-2) → C30H25N4O2(1+)*Cl(1-)

Conditions	Yield
With pyridine at 120℃; for 12h; Inert atmosphere;	60%

3-amino-7-(diethylamino)-5-phenylphenazinium chloride (4569-86-2) → 3-hydroxy-7-(diethylamino)-5-phenylphenazinium chloride

Conditions	Yield
Stage #1: 3-amino-7-(diethylamino)-5-phenylphenazinium chloride With sulfuric acid In water Stage #2: With sodium nitrite In water at -10 - 20℃; for 1.5h; Stage #3: With sulfuric acid; water; copper(II) sulfate at 105℃; for 3h;	40%

2,2'-(phenylimino)bis[ethanol] (120-07-0) + 3-amino-7-(diethylamino)-5-phenylphenazinium chloride (4569-86-2) → 3-diethylamino-5-phenylphenazium-7-(4'-N,N-di(2-hydroxyethyl)azobenzene) chloride

Conditions	Yield
Stage #1: 3-amino-7-(diethylamino)-5-phenylphenazinium chloride With hydrogenchloride; sodium nitrite In methanol; water for 0.833333h; Cooling with ice; Stage #2: 2,2'-(phenylimino)bis[ethanol] With sodium hydroxide In methanol; water for 1h; pH=6;	21%

1-[methyl(phenyl)amino]propan-2-one (15885-06-0) + 3-amino-7-(diethylamino)-5-phenylphenazinium chloride (4569-86-2) + trifluoroacetic acid (76-05-1) → C31H31N6O(1+)*C2F3O2(1-)

Conditions	Yield
Stage #1: 3-amino-7-(diethylamino)-5-phenylphenazinium chloride With nitrosonium tetrafluoroborate In acetonitrile at 0℃; for 0.25h; Stage #2: 1-[methyl(phenyl)amino]propan-2-one In acetonitrile at 0℃; for 1h; Stage #3: trifluoroacetic acid	17%

3-(methyl(phenyl)amino)propane-1,2-diol (42871-95-4) + 3-amino-7-(diethylamino)-5-phenylphenazinium chloride (4569-86-2) + trifluoroacetic acid (76-05-1) → C32H35N6O2(1+)*C2F3O2(1-) (1432152-08-3)

Conditions	Yield
Stage #1: 3-amino-7-(diethylamino)-5-phenylphenazinium chloride With nitrosonium tetrafluoroborate In acetonitrile at 0℃; for 0.25h; Stage #2: 3-(methyl(phenyl)amino)propane-1,2-diol In acetonitrile at 0℃; for 1h; Stage #3: trifluoroacetic acid	6%

3-amino-7-(diethylamino)-5-phenylphenazinium chloride (4569-86-2) → 3-amino-7-ethylamino-5-phenylphenazinium 10-N-oxide

Conditions	Yield
With sodium chlorite; sulfuric acid In water Kinetics; Further Variations:; Catalysts;

4-bromobutyroyl chloride (927-58-2) + 3-amino-7-(diethylamino)-5-phenylphenazinium chloride (4569-86-2) → C26H28BrN4O(1+)*Cl(1-)

Conditions	Yield
In 1-methyl-pyrrolidin-2-one at 20℃; for 17h;

3-amino-7-(diethylamino)-5-phenylphenazinium chloride (4569-86-2) → C41H40N9O2(1+)*C2F3O2(1-) (1432152-16-3)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: nitrosonium tetrafluoroborate / acetonitrile / 0.25 h / 0 °C 1.2: 1 h / 0 °C 2.1: sodium 2-(1,2-dihydroxyethyl)-4-hydroxy-5-oxo-2,5-dihydro-furan-3-olate; copper(ll) sulfate pentahydrate / dimethyl sulfoxide; water / 2 h / 20 °C / Inert atmosphere View Scheme

3-amino-7-(diethylamino)-5-phenylphenazinium chloride (4569-86-2) → C39H41N11O7S*C2HF3O2 (1432152-23-2)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: nitrosonium tetrafluoroborate / acetonitrile / 0.25 h / 0 °C 1.2: 1 h / 0 °C 2.1: sodium 2-(1,2-dihydroxyethyl)-4-hydroxy-5-oxo-2,5-dihydro-furan-3-olate; copper(ll) sulfate pentahydrate / dimethyl sulfoxide; water / 2 h / 20 °C / Inert atmosphere View Scheme

3-amino-7-(diethylamino)-5-phenylphenazinium chloride (4569-86-2) → 3-diethylamino-5-phenylphenazium-7-(4'-N,N-(2-hydroxyethyl)-(2-O-(4,4'-dimethoxytrityl)ethyl))azobenzene chloride

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium nitrite; hydrogenchloride / water; methanol / 0.83 h / Cooling with ice 1.2: 1 h / pH 6 2.1: pyridine View Scheme

3-amino-7-(diethylamino)-5-phenylphenazinium chloride (4569-86-2) → 3-diethylamino-5-phenylphenazium-7-(4'-N,N-(2-O-(N,N'-diisopropyl-2-cyanoethylphosphite)ethyl))-(2-O-(4,4'-dimethoxytrityl)ethyl)azobenzene chloride

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium nitrite; hydrogenchloride / water; methanol / 0.83 h / Cooling with ice 1.2: 1 h / pH 6 2.1: pyridine 3.1: 1H-tetrazole / acetonitrile / 2 h View Scheme

3-amino-7-(diethylamino)-5-phenylphenazinium chloride (4569-86-2) → C28H33N6O(1+)*Cl(1-)

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 8 h / 20 °C 2: potassium carbonate / acetonitrile / 2 h / 20 °C View Scheme

3-amino-7-(diethylamino)-5-phenylphenazinium chloride (4569-86-2) → 3RAX-N-NBD-2

Conditions	Yield
Multi-step reaction with 3 steps 1: triethylamine / dichloromethane / 8 h / 20 °C 2: potassium carbonate / acetonitrile / 2 h / 20 °C 3: triethylamine / dichloromethane / 15 h / 40 °C View Scheme

3-amino-7-(diethylamino)-5-phenylphenazinium chloride (4569-86-2) + chloroacetyl chloride (79-04-9) → C24H24ClN4O(1+)*Cl(1-)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 8h;

4-phenyl-1-piperazine (92-54-6) + 3-amino-7-(diethylamino)-5-phenylphenazinium chloride (4569-86-2) → C32H34N7(1+)*Cl(1-)

Conditions	Yield
With hydrogenchloride In water for 3h;

Upstream product

• 62-53-3 aniline 
• 93-05-0 N,N-diethylaniline 

Downstream Products

• 1432152-08-3 C₃₂H₃₅N₆O₂⁽¹⁺⁾*C₂F₃O₂^(1-) 
• 1432151-27-3 C₃₁H₃₂N₉⁽¹⁺⁾*C₂F₃O₂^(1-) 
• 1432152-23-2 C₃₉H₄₁N₁₁O₇S*C₂HF₃O₂ 
• 1432152-16-3 C₄₁H₄₀N₉O₂⁽¹⁺⁾*C₂F₃O₂^(1-) 
• 1432152-01-6 C₃₄H₃₅N₆⁽¹⁺⁾*C₂F₃O₂^(1-) 

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