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

Chemical Properties

dark green powder

Uses

Different sources of media describe the Uses of 553-24-2 differently. You can refer to the following data:
1. Neutral Red is used as indicator for nitrogen determination; pH indicator.
2. Neutral Red is a common histology stain used to determine cell viability.Dyes and metabolites.
3. Can be used as a vital stain, to stain living cells.

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.

Definition

ChEBI: A hydrochloride obtained by combining the free base of neutral red with one equivalent of hydrochloric acid. Neutral red acts as a pH indicator, changing from red to yellow between pH 6.8 and 8.0.

General Description

Neutral red (C.I. 50040) is a protonated diaminophenazine dye. It is aminodimethylaminomethylphenazinehydrochloride, C15H17N4Cl.

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.

Properties and Applications

red light purple and red. Soluble in water is cherry red, soluble in ethanol for product red colour with red fluorescent light brown. The strong sulfuric acid for green, blue for diluted, and then into a product red. The dye solution to join strong sodium hydroxide solution have yellow brown precipitation.

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;