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

Description

CI 50206, also known as Methylene Violet 3RAX, is a chemical compound that is used in various applications across different industries. It is known for its unique properties and characteristics that make it suitable for specific uses.

Uses

Used in Chemical Synthesis:
CI 50206 is used as a starting material in the preparation of methylene violet derivatives, which serve as fluorescent probes for the detection of sulfide ions. This application is particularly useful in chemical research and analysis.
Used in Microbiology:
In the field of microbiology, CI 50206 is used as a reagent in the preparation of citrate methylene violet. CI 50206 is utilized for staining yeast cells, aiding in their identification and examination under a microscope.
Used in Mass Spectrometry:
CI 50206 also finds application in the field of analytical chemistry, specifically in tandem mass spectrometry (MS/MS). It is used as an internal standard for the quantification of methylene blue in blood samples, ensuring accurate and reliable measurements.

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

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

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