553-24-2

Basic information

• Product Name: Basic Red 5
• Synonyms: 2,8-Phenazinediamine,N8,N8-3-trimethyl-,monohydrochloride;3-amino-7-(dimethylamino)-2-methyl-phenazinhydrochloride;3-amino-7-(dimethylamino)-2-methyl-phenazinmonohydrochloride;8-phenazinediamine,n8,n8,3-trimethyl-monohydrochloride;aminodimethylaminotoluaminozinehydrochloride;c.i.basicred5;c.i.basicred5,monohydrochloride;cervenneutralni
• CAS NO: 553-24-2
• Molecular Formula: C15H17ClN4
• Molecular Weight: 288.77528
• EINECS: 209-035-8
• Product Categories: Organics;Analytical Chemistry;Indicator (pH);pH Indicators;Stains and Dyes;marker;Azine;Miscellaneous;Phenazine
• Mol File: 553-24-2.mol
• Article Data: 0

Chemical Properties

• Melting Point: 290 °C (dec.)(lit.)
• Boiling Point: 441.31°C (rough estimate)
• Flash Point: 254.6 °C
• Appearance: Very dark green/Solid
• Density: 1.1590 (rough estimate)
• Refractive Index: 1.6110 (estimate)
• Storage Temp.: Store at 0-5°C
• Solubility: H2O: soluble10mg/mL
• PKA: 6.7, 7.4(at 25℃)
• Water Solubility: 50 g/L
• Stability: Stable. Incompatible with strong oxidizing agents.
• Merck: 14,6488
• BRN: 3918740
• CAS DataBase Reference: Basic Red 5(CAS DataBase Reference)
• NIST Chemistry Reference: Basic Red 5(553-24-2)
• EPA Substance Registry System: Basic Red 5(553-24-2)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 68-36/37/38
• Safety Statements: 36/37-37/39-36-26-24/25
• WGK Germany: 3
• RTECS: SG1400000
• TSCA: Yes
• Hazardous Substances Data: 553-24-2(Hazardous Substances Data)

Usage

Description

Basic Red 5, also known as Neutral Red, is a protonated diaminophenazine dye with the chemical formula C15H17N4Cl. It is a hydrochloride obtained by combining the free base of neutral red with one equivalent of hydrochloric acid. Basic Red 5 exhibits properties such as being a dark green powder and changing colors in response to pH levels, turning from red to yellow between pH 6.8 and 8.0.

Uses

Used in Chemical Analysis:
Basic Red 5 is used as an indicator for nitrogen determination in various chemical analyses. Its color-changing properties make it a useful tool for detecting the presence of nitrogen in samples.
Used in Histology:
In the field of histology, Basic Red 5 is a common stain used to determine cell viability. It helps in differentiating between living and dead cells, providing valuable information for researchers studying cell health and function.
Used as a Vital Stain:
Basic Red 5 can be used as a vital stain to stain living cells. Its ability to penetrate and color living cells without causing significant harm makes it a valuable tool in cell biology and microscopy.
Used in Dyes and Metabolites:
The dye properties of Basic Red 5 make it suitable for use in the production of various dyes and metabolites. Its red color with red fluorescent light brown is achieved when it is soluble in ethanol, while a cherry red color is obtained when it is soluble in water.
Used in pH Indication:
Due to its color-changing properties in response to pH levels, Basic Red 5 is used as a pH indicator. It changes from red to yellow between pH 6.8 and 8.0, making it a useful tool for monitoring and controlling pH levels in various applications.

Preparation

(a) N,N-dimethyl-4-nitrosobenzenamine?and 4-Methylbenzene-1,3-diamine???reaction, form Toluylene Blue (Basic Dye, C.I. 49410), heating make cyclization; (b) oxidation N1,N1-dimethylbenzene-1,4-diamine?, and 4-Methylbenzene-1,3-diamine mixture.

Biochem/physiol Actions

Neutral red is a widely used cationic fluorochrome that is known to accumulate in the Golgi complex and nuclei after first staining lysosomes.

Purification Methods

In aqueous solution it is red at pH 6.8 and yellow at pH 8.0. [Beilstein 25 III/IV 3054.]

InChI:InChI=1/C15H16N4.ClH/c1-9-6-13-15(8-11(9)16)18-14-7-10(19(2)3)4-5-12(14)17-13;/h4-8H,1-3H3,(H2,16,18);1H

Synthetic route

tetrafluoroboric acid + neutral red (553-24-2) → 3-methyl-7-dimethylaminophenazine-2-diazonium tetrafluoroborate

Conditions	Yield
With sodium nitrite In water for 2h;	68%

neutral red (553-24-2) → 3,N8,N8-trimethyl-5,10-dihydro-phenazine-2,8-diamine (31160-45-9)

Conditions	Yield
With sodium dithionite bei pH 8.2;

tetrafluoroboric acid + neutral red (553-24-2) → 3-methyl-7-dimethylaminophenazine-2-diazonium tetrafluoroborate

Conditions	Yield
With sodium nitrite In water for 2h;	68%

neutral red (553-24-2) → 3,N8,N8-trimethyl-5,10-dihydro-phenazine-2,8-diamine (31160-45-9)

Conditions	Yield
With sodium dithionite bei pH 8.2;

neutral red (553-24-2) → 3-amino-7-dimethylamino-2,5-dimethyl-phenazinium; chloride-hydrochloride

Conditions	Yield
beim Acetylieren;

neutral red (553-24-2) → 3-amino-7-dimethylamino-2,5-dimethyl-phenazinium; iodide

Conditions	Yield
beim Acetylieren;

neutral red (553-24-2) + nitrobenzene (98-95-3) + dimethyl sulfate (77-78-1) → 3-amino-6-dimethylamino-2-methyl-phenazine chloromethylate-(10)

Conditions	Yield
at 160 - 170℃; folgendes Kochen mit Salzsaeure;

neutral red (553-24-2) + methyl iodide (74-88-4) → 3-amino-6-dimethylamino-2-methyl-phenazine chloromethylate-(10)

Conditions	Yield
at 100℃; folgendes Kochen mit Salzsaeure;

ethanol (64-17-5) + sulfuric acid (7664-93-9) + neutral red (553-24-2) + sodium nitrite → 6-dimethylamino-2-methyl-phenazine

neutral red (553-24-2) → dimer

Conditions	Yield
In water at 40℃; Thermodynamic data; Equilibrium constant; further temperatures, solvents, salts, ΔG(activ.), ΔH(activ.), ΔS(activ.);

C86H142O70 (1239692-34-2) + neutral red (553-24-2) → C15H16N4*C86H142O70

Conditions	Yield
at 25℃; pH=7.2; aq. phosphate buffer;

C88H146O71 (1239692-35-3) + neutral red (553-24-2) → C15H16N4*C88H146O71

Conditions	Yield
at 25℃; pH=7.2; aq. phosphate buffer;

C90H150O72 (1239692-36-4) + neutral red (553-24-2) → C15H16N4*C90H150O72

Conditions	Yield
at 25℃; pH=7.2; aq. phosphate buffer;

neutral red (553-24-2) + tetrasodium 25,26,27,28-tetrahydroxycalix[4]arene-5,11,17,23-tetrasulfonate (110242-20-1, 114245-69-1, 116888-13-2) → C15H16N4*C28H20O16S4(4-)*4Na(1+)

Conditions	Yield
at 25℃; pH=4.5; aq. acetate buffer;

neutral red (553-24-2) + sodium p-sulfonatocalix[6]arene (96107-96-9, 145344-64-5) → C15H16N4*C42H30O24S6(6-)*6Na(1+)

Conditions	Yield
at 25℃; pH=4.5; aq. acetate buffer;

neutral red (553-24-2) + octasodium salt of 5,11,17,23,29,35,41,47-octasulfonatocalix<8>arene (105190-41-8, 114324-27-5) → C15H16N4*C56H40O32S8(8-)*8Na(1+)

Conditions	Yield
at 25℃; pH=4.5; aq. acetate buffer;

C46H48N8O20S4(4-)*4Na(1+) + neutral red (553-24-2) → 4Na(1+)*ClH*C15H16N4*C46H48N8O20S4(4-)

Conditions	Yield
In aq. phosphate buffer; water-d2 pH=7.4;

neutral red (553-24-2) + calix[4]arene-5,11,17,23-tetrasulfonate → C28H20O16S4(4-)*C15H16N4*ClH

Conditions	Yield
In water

neutral red (553-24-2) + calix[6]arene-p-hexasulfonate → C42H30O24S6(6-)*C15H16N4*ClH

Conditions	Yield
In water pH=Ca. 5;

C66H72N20O24 + neutral red (553-24-2) → C66H72N20O24*C15H16N4*ClH

Conditions	Yield
In aq. phosphate buffer pH=7.5;

C66H80N20O24 + neutral red (553-24-2) → C66H80N20O24*C15H16N4*ClH

Conditions	Yield
In aq. phosphate buffer pH=7.5;

carboxylatopillar[5]arene sodium salt + neutral red (553-24-2) → C15H16N4*ClH*C55H40O30(10-)

Conditions	Yield
In aq. phosphate buffer pH=7.4; Kinetics;