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4569-86-2

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.

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  • 4569-86-2 Structure

  • Basic information

    1. Product Name: CI 50206
    2. 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
    3. CAS NO:4569-86-2
    4. Molecular Formula: C22H23N4*Cl
    5. Molecular Weight: 378.9
    6. EINECS: 610-268-6
    7. Product Categories: N/A
    8. Mol File: 4569-86-2.mol

  • Chemical Properties

    1. Melting Point: 285 °C (dec.)(lit.)
    2. Boiling Point: N/A
    3. Flash Point: N/A
    4. Appearance: dark green crystalline powder
    5. Density: N/A
    6. Refractive Index: N/A
    7. Storage Temp.: room temp
    8. Solubility: N/A
    9. CAS DataBase Reference: CI 50206(CAS DataBase Reference)
    10. NIST Chemistry Reference: CI 50206(4569-86-2)
    11. EPA Substance Registry System: CI 50206(4569-86-2)

  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: 24/25
    4. WGK Germany: 3
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 4569-86-2(Hazardous Substances Data)

4569-86-2 Usage

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.

Check Digit Verification of cas no

The CAS Registry Mumber 4569-86-2 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,5,6 and 9 respectively; the second part has 2 digits, 8 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 4569-86:
(6*4)+(5*5)+(4*6)+(3*9)+(2*8)+(1*6)=122
122 % 10 = 2
So 4569-86-2 is a valid CAS Registry Number.
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

4569-86-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 20, 2017

Revision Date: Aug 20, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-N,2-N-diethyl-10-phenylphenazin-10-ium-2,8-diamine,chloride

1.2 Other means of identification

Product number -
Other names methylene violet

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:4569-86-2 SDS

4569-86-2Synthetic route

aniline
62-53-3

aniline

N,N-diethylaniline
93-05-0

N,N-diethylaniline

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

3-amino-7-(diethylamino)-5-phenylphenazinium chloride

Conditions
ConditionsYield
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

3-amino-7-(diethylamino)-5-phenylphenazinium chloride

4-(10,15,20-triphenyl-21H,23H-porphin-5-yl)benzoic acid

4-(10,15,20-triphenyl-21H,23H-porphin-5-yl)benzoic acid

C67H51N8O(1+)*Cl(1-)

C67H51N8O(1+)*Cl(1-)

Conditions
ConditionsYield
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

3-amino-7-(diethylamino)-5-phenylphenazinium chloride

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
53-86-1

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

C41H37ClN5O3(1+)*Cl(1-)

C41H37ClN5O3(1+)*Cl(1-)

Conditions
ConditionsYield
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

3-amino-7-(diethylamino)-5-phenylphenazinium chloride

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

3-(4-methylbenzenesulfonamido)-7-(diethylamino)-5-phenylphenazinium chloride

3-(4-methylbenzenesulfonamido)-7-(diethylamino)-5-phenylphenazinium chloride

Conditions
ConditionsYield
With triethylamine In chloroform at 60℃; for 2h;78%
3-amino-7-(diethylamino)-5-phenylphenazinium chloride
4569-86-2

3-amino-7-(diethylamino)-5-phenylphenazinium chloride

3-bromo-7-N,N-diethylamino-5-phenyl-phenazinium bromide

3-bromo-7-N,N-diethylamino-5-phenyl-phenazinium bromide

Conditions
ConditionsYield
With hydrogen bromide; sodium nitrite In water at 50℃; for 2h;67%
N-(2-azidoethyl)-N-methylaniline
1249429-26-2

N-(2-azidoethyl)-N-methylaniline

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

3-amino-7-(diethylamino)-5-phenylphenazinium chloride

trifluoroacetic acid
76-05-1

trifluoroacetic acid

C31H32N9(1+)*C2F3O2(1-)
1432151-27-3

C31H32N9(1+)*C2F3O2(1-)

Conditions
ConditionsYield
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

N-methyl-N-(pent-4-ynyl)aniline

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

3-amino-7-(diethylamino)-5-phenylphenazinium chloride

trifluoroacetic acid
76-05-1

trifluoroacetic acid

C34H35N6(1+)*C2F3O2(1-)
1432152-01-6

C34H35N6(1+)*C2F3O2(1-)

Conditions
ConditionsYield
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

phthalic anhydride

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

3-amino-7-(diethylamino)-5-phenylphenazinium chloride

C30H25N4O2(1+)*Cl(1-)

C30H25N4O2(1+)*Cl(1-)

Conditions
ConditionsYield
With pyridine at 120℃; for 12h; Inert atmosphere;60%
3-amino-7-(diethylamino)-5-phenylphenazinium chloride
4569-86-2

3-amino-7-(diethylamino)-5-phenylphenazinium chloride

3-hydroxy-7-(diethylamino)-5-phenylphenazinium chloride

3-hydroxy-7-(diethylamino)-5-phenylphenazinium chloride

Conditions
ConditionsYield
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

2,2'-(phenylimino)bis[ethanol]

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

3-amino-7-(diethylamino)-5-phenylphenazinium chloride

3-diethylamino-5-phenylphenazium-7-(4'-N,N-di(2-hydroxyethyl)azobenzene) chloride

3-diethylamino-5-phenylphenazium-7-(4'-N,N-di(2-hydroxyethyl)azobenzene) chloride

Conditions
ConditionsYield
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

1-[methyl(phenyl)amino]propan-2-one

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

3-amino-7-(diethylamino)-5-phenylphenazinium chloride

trifluoroacetic acid
76-05-1

trifluoroacetic acid

C31H31N6O(1+)*C2F3O2(1-)

C31H31N6O(1+)*C2F3O2(1-)

Conditions
ConditionsYield
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-(methyl(phenyl)amino)propane-1,2-diol

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

3-amino-7-(diethylamino)-5-phenylphenazinium chloride

trifluoroacetic acid
76-05-1

trifluoroacetic acid

C32H35N6O2(1+)*C2F3O2(1-)
1432152-08-3

C32H35N6O2(1+)*C2F3O2(1-)

Conditions
ConditionsYield
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-(diethylamino)-5-phenylphenazinium chloride

3-amino-7-ethylamino-5-phenylphenazinium 10-N-oxide

3-amino-7-ethylamino-5-phenylphenazinium 10-N-oxide

Conditions
ConditionsYield
With sodium chlorite; sulfuric acid In water Kinetics; Further Variations:; Catalysts;
4-bromobutyroyl chloride
927-58-2

4-bromobutyroyl chloride

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

3-amino-7-(diethylamino)-5-phenylphenazinium chloride

C26H28BrN4O(1+)*Cl(1-)

C26H28BrN4O(1+)*Cl(1-)

Conditions
ConditionsYield
In 1-methyl-pyrrolidin-2-one at 20℃; for 17h;
3-amino-7-(diethylamino)-5-phenylphenazinium chloride
4569-86-2

3-amino-7-(diethylamino)-5-phenylphenazinium chloride

C41H40N9O2(1+)*C2F3O2(1-)
1432152-16-3

C41H40N9O2(1+)*C2F3O2(1-)

Conditions
ConditionsYield
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-amino-7-(diethylamino)-5-phenylphenazinium chloride

C39H41N11O7S*C2HF3O2
1432152-23-2

C39H41N11O7S*C2HF3O2

Conditions
ConditionsYield
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-amino-7-(diethylamino)-5-phenylphenazinium chloride

3-diethylamino-5-phenylphenazium-7-(4'-N,N-(2-hydroxyethyl)-(2-O-(4,4'-dimethoxytrityl)ethyl))azobenzene chloride

3-diethylamino-5-phenylphenazium-7-(4'-N,N-(2-hydroxyethyl)-(2-O-(4,4'-dimethoxytrityl)ethyl))azobenzene chloride

Conditions
ConditionsYield
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-amino-7-(diethylamino)-5-phenylphenazinium chloride

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

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
ConditionsYield
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

3-amino-7-(diethylamino)-5-phenylphenazinium chloride

C28H33N6O(1+)*Cl(1-)

C28H33N6O(1+)*Cl(1-)

Conditions
ConditionsYield
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

3-amino-7-(diethylamino)-5-phenylphenazinium chloride

3RAX-N-NBD-2

3RAX-N-NBD-2

Conditions
ConditionsYield
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

3-amino-7-(diethylamino)-5-phenylphenazinium chloride

chloroacetyl chloride
79-04-9

chloroacetyl chloride

C24H24ClN4O(1+)*Cl(1-)

C24H24ClN4O(1+)*Cl(1-)

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 8h;
4-phenyl-1-piperazine
92-54-6

4-phenyl-1-piperazine

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

3-amino-7-(diethylamino)-5-phenylphenazinium chloride

C32H34N7(1+)*Cl(1-)

C32H34N7(1+)*Cl(1-)

Conditions
ConditionsYield
With hydrogenchloride In water for 3h;

4569-86-2Relevant articles and documents

Methylene violet 3RAX-conjugated porphyrin for photodynamic therapy: Synthesis, DNA photocleavage, and cell study

Yao, Si,Zheng, Yunman,Jiang, Lijun,Xie, Chen,Wu, Fengshou,Huang, Chi,Zhang, Xiong,Wong, Ka-Leung,Li, Zaoying,Wang, Kai

, p. 4472 - 4477 (2018)

A methylene violet 3RAX-conjugated porphyrin has been designed and synthesized as a potential photosensitizer in photodynamic therapy because of its high DNA binding constant and the efficacy in inhibiting cancer cells with subcellular localization.

DNA Photocleavage and Binding Modes of Methylene Violet 3RAX and its Derivatives: Effect of Functional Groups

Yang, Ke,Zhang, Xiong,Yang, Fang,Wu, Fengshou,Zhang, Xiulan,Wang, Kai

, p. 830 - 836 (2017)

With 4′-amino-N,N-diethylaniline and aniline as starting materials, methylene violet 3RAX 1 and its derivatives 2-5 were synthesised. The five compounds were characterised by IR, UV-vis, and 1H NMR spectroscopy and mass spectrometry. The binding mode between the synthesised compounds and DNA were investigated. The results show that both compounds 1 and 5 bind to DNA by an intercalative mode, while compounds 2-4 interact with DNA through a mixed binding mode involving groove binding and electrostatic interactions. The photocleavage ability of the five compounds to DNA were calculated to be 38, 40, 30, 20, and 13%, respectively, when their concentration was adjusted to 400M. The singlet oxygen production of compounds measured by the 1,3-diphenylisobenzofuran method was consistent with the trend of DNA photocleavage ability. The DNA studies suggest that the binding mode between methylene violet 3RAX and DNA, the ability of methylene violet 3RAX to generate singlet oxygen, and the DNA photocleavage activity could be adjusted through modification of the amino group on methylene violet 3RAX.

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