477-73-6

Basic information

• Product Name: Basic Red 2
• Synonyms: S NO 967;SAFRANIN A;SAFRANIN;SAFRANINE;SAFRANINE A,O,T,Y;SAFRANINE B;SAFRANINE O;SAFRANINE ''O''
• CAS NO: 477-73-6
• Molecular Formula: C₂₀H₁₉N₄*Cl
• Molecular Weight: 350.84
• EINECS: 207-518-8
• Product Categories: S;Stains and Dyes;Stains&Dyes, A to;Phenazine
• Mol File: 477-73-6.mol
• Article Data: 0

Chemical Properties

• Melting Point: >240℃ (decompose)
• Boiling Point: 507.14°C (rough estimate)
• Flash Point: 46 °C
• Appearance: S. No.: 967/Solid
• Density: 1.00 g/mL at 20 °C
• Refractive Index: n20/D 1.339
• Storage Temp.: Store at RT.
• Solubility: H2O: soluble1mg/mL
• PKA: 6.4(at 25℃)
• Water Solubility: soluble
• Stability: Stable.
• BRN: 3924099
• CAS DataBase Reference: Basic Red 2(CAS DataBase Reference)
• NIST Chemistry Reference: Basic Red 2(477-73-6)
• EPA Substance Registry System: Basic Red 2(477-73-6)

Safety Data

• Hazard Codes: Xi
• Statements: 41-36/38-37/38-10-36/37/38
• Safety Statements: 26-39-24/25-36-16
• RIDADR: UN 1170 3/PG 3
• WGK Germany: 3
• RTECS: SG1623000
• TSCA: Yes
• Hazardous Substances Data: 477-73-6(Hazardous Substances Data)

Usage

Description

Basic Red 2 is a red dye that fluoresces when exposed to selected wavelengths of light. It is a dark red to violet powder that is soluble in water for red, soluble in ethanol with yellow-red fluorescent red. The strong sulfuric acid turns it green, and when diluted by blue, it becomes red. The dye solution, when joined with sodium hydroxide, produces a light brown red precipitate, and when joined with hydrochloric acid, it turns blue-purple.

Uses

Used in Biological Staining:
Basic Red 2 is used as a biological stain for staining Gram-negative bacteria, chromosomes, mucin, cartilage, and mast cells. It is particularly useful in the field of environmental testing and dyes and metabolites analysis.
Used in Forensic Science:
In forensics, Basic Red 2 is used to visualize details of cyanoacrylate-fumed friction ridges of human digits, aiding in the identification and analysis of fingerprints.
Used in Textile Industry:
Basic Red 2 is used in the paper-making industry and color-up manufacturing. It is also used for dyeing acrylic, linen, and silk products. The dye has standard properties such as light fastness (C 1-2), perspiration fastness (2), ironing fastness (2-3), soaping (2-3), and fading (5).

Preparation

commonly known as Safranine T. Such molecular ratio of 2-Methylbenzene-1 ,4-diamine, and O-Methylaniline oxidation, the resulting condensation product of aniline and purified by precipitation segmented dye, and then converted to the chloride.

Standard( Cotton )

Light Fastness

Fading

Stain

C

1-2

Purification Methods

Crystallise it from *benzene/MeOH (1:1) or water. Dry it in vacuo over H2SO4. It has UV: at 520nm (H2O) and 530nm (EtOH). [Beilstein 25 H 403, 25 I 657, 25 III/IV

InChI:InChI=1/C20H18N4.ClH/c1-12-8-17-19(10-15(12)21)24(14-6-4-3-5-7-14)20-11-16(22)13(2)9-18(20)23-17;/h3-11H,1-2H3,(H3,21,22);1H

Synthetic route

o-toluidine (95-53-4) → safranin O (477-73-6)

Conditions	Yield
With cis-nitrous acid Reduktion mit Zink oder Eisen +Salzsaeure und Oxidation in Gegenwart von Anilin mit Kaliumdichromat oder Braunstein.;
With cis-nitrous acid Reduktion mit Zink oder Eisen +Salzsaeure und Oxidation in Gegenwart von Anilin mit Kaliumdichromat oder Braunstein.;

10-phenyl-3-acetylamino-2,7-dimethyl-phenazinium chloride + ammonia → safranin O (477-73-6)

Conditions	Yield
With ethanol

2-methyl-p-phenylenediamine (95-70-5) → safranin O (477-73-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: calcium chloride 2: alcohol View Scheme

N,N'-dichloro-2-methyl-cyclohexa-2,5-diene-1,4-diylidenediamine (3029-60-5) + 4-methyl-N1-phenylbenzene-1,3-diamine (6406-71-9) → safranin O (477-73-6)

Conditions	Yield
With ethanol

1,8-dibromooctane (4549-32-0) + safranin O (477-73-6)

Conditions	Yield
Stage #1: safranin O With potassium carbonate In N,N-dimethyl acetamide at 20℃; for 0.25h; Stage #2: 1,8-dibromooctane With potassium iodide In N,N-dimethyl acetamide at 60℃; for 24h; Inert atmosphere;
Stage #1: safranin O With potassium carbonate In N,N-dimethyl acetamide at 20℃; for 0.25h; Stage #2: 1,8-dibromooctane With potassium iodide In N,N-dimethyl acetamide at 60℃; for 24h; Inert atmosphere;
Stage #1: safranin O With potassium carbonate In N,N-dimethyl acetamide at 20℃; for 0.25h; Stage #2: 1,8-dibromooctane With potassium iodide In N,N-dimethyl acetamide at 60℃; for 24h; Inert atmosphere;

di-tert-butyl dicarbonate (24424-99-5) + safranin O (477-73-6) → 3-amino-7-(tert-butoxy carbonylamino)-2,8-dimethyl-5-phenylphenazin-5-ium chloride

Conditions	Yield
Stage #1: safranin O With sodium hydride In N,N-dimethyl-formamide at -40℃; for 1h; Stage #2: di-tert-butyl dicarbonate In N,N-dimethyl-formamide at -40℃; for 1h;	1 g
Stage #1: safranin O With sodium hydride In N,N-dimethyl-formamide at -40℃; for 1h; Stage #2: di-tert-butyl dicarbonate In N,N-dimethyl-formamide at -40℃; for 1h;	1 g
Stage #1: safranin O With sodium hydride In N,N-dimethyl-formamide at -40℃; for 1h; Stage #2: di-tert-butyl dicarbonate In N,N-dimethyl-formamide at -40℃; for 1h;	1 g
Stage #1: safranin O With sodium hydride In N,N-dimethyl-formamide at -40℃; for 1h; Stage #2: di-tert-butyl dicarbonate In N,N-dimethyl-formamide at -40℃; for 1h;	1 g
Stage #1: safranin O With sodium hydride In N,N-dimethyl-formamide at -40℃; for 1h; Stage #2: di-tert-butyl dicarbonate In N,N-dimethyl-formamide at -40℃; for 1h;	1 g

sodium thiocyanide (540-72-7) + safranin O (477-73-6) → 7-amino-2,8-dimethyl-3-thiocyanato-5-phenyl-phenazinium tetrafluoroborate

Conditions	Yield
With tetrafluoroboric acid; sodium nitrite In water at 50 - 60℃; for 2h;	64%

safranin O (477-73-6) + bis(2,5-dioxopyrrolidin-1-yl) undecanedioate → (3-amino-7-{10-[(7-amino-5-chloranuide-2,8-dimethyl-5-phenyl-5λ6,10-phenazin-5-ylium-3-yl)carbamoyl]decanamido}-2,8-dimethyl-5-phenyl-5λ6,10-phenazin-5-ylium-5-e)chloranuide

Conditions	Yield
Stage #1: safranin O With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.166667h; Stage #2: bis(2,5-dioxopyrrolidin-1-yl) undecanedioate In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 16h; Stage #3: With hydrogenchloride In methanol	5 mg
Stage #1: safranin O With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.166667h; Stage #2: bis(2,5-dioxopyrrolidin-1-yl) undecanedioate In N,N-dimethyl-formamide at 20℃; for 16h; Stage #3: With hydrogenchloride In methanol	5 mg
Stage #1: safranin O With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.166667h; Stage #2: bis(2,5-dioxopyrrolidin-1-yl) undecanedioate In N,N-dimethyl-formamide at 0 - 20℃; for 16h; Stage #3: With hydrogenchloride In methanol	5 mg
Stage #1: safranin O With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.166667h; Stage #2: bis(2,5-dioxopyrrolidin-1-yl) undecanedioate In N,N-dimethyl-formamide at 0 - 20℃; for 16h;	5 mg

safranin O (477-73-6) + bis(2,5-dioxopyrrolidin-1-yl) undecanedioate → (3-amino-7-{10-[(7-amino-5-chloranuide-2,8-dimethyl-5-phenyl-5λ6,10-phenazin-5-ylium-3-yl)carbamoyl]decanamido}-2,8-dimethyl-5-phenyl-5λ6,10-phenazin-5-ylium-5-yl)chloranuide

Conditions	Yield
Stage #1: safranin O With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.166667h; Stage #2: bis(2,5-dioxopyrrolidin-1-yl) undecanedioate In N,N-dimethyl-formamide at 20℃; for 16h;	5 mg
Stage #1: safranin O With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.166667h; Stage #2: bis(2,5-dioxopyrrolidin-1-yl) undecanedioate In N,N-dimethyl-formamide at 0 - 20℃; for 16h;	5 mg

di-tert-butyl dicarbonate (24424-99-5) + safranin O (477-73-6) → 3,7-bis(tert-butoxycarbonylamino)-2,8-dimethyl-5-phenylphenazin-5-ium dichloride + 3,7-bis(tert-butoxycarbonylamino)-2,6-dimethyl-5-phenylphenazin-5-ium chloride

Conditions	Yield
Stage #1: safranin O With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 0.25h; Stage #2: di-tert-butyl dicarbonate In N,N-dimethyl-formamide at 20℃; for 2h; Overall yield = 5 g;
Stage #1: safranin O With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 0.25h; Stage #2: di-tert-butyl dicarbonate In N,N-dimethyl-formamide at 20℃; for 2h; Overall yield = 5 g;

di-tert-butyl dicarbonate (24424-99-5) + safranin O (477-73-6) → 3-amino-7-(tert-butoxycarbonylamino)-2,8-dimethyl-5-phenylphenazin-5-ium chloride

Conditions	Yield
Stage #1: safranin O With sodium hydride In N,N-dimethyl-formamide; mineral oil at -40℃; for 1h; Stage #2: di-tert-butyl dicarbonate In N,N-dimethyl-formamide; mineral oil at -40℃; for 1h;	1 g

1,8-diiodooctane (24772-63-2) + di-tert-butyl dicarbonate (24424-99-5) + safranin O (477-73-6) → 7,7’-(octane-1,8-diylbis(azanediyl)) bis(3-amino-2,8-dimethyl-5-phenylphenazin-5-ium)chloride + 3-amino-7-(8-(7-amino-2,8-dimethyl-5-phenylphenazin-5-ium-3-ylamino)octylamino)-2,6-dimethyl-5-phenylphenazin-5-ium dichloride

Conditions	Yield
Stage #1: safranin O With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 0.25h; Stage #2: di-tert-butyl dicarbonate In N,N-dimethyl-formamide at 20℃; for 2h; Stage #3: 1,8-diiodooctane Further stages;
Stage #1: safranin O With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 0.25h; Stage #2: di-tert-butyl dicarbonate In N,N-dimethyl-formamide at 20℃; for 2h; Stage #3: 1,8-diiodooctane Further stages;

1,8-diiodooctane (24772-63-2) + di-tert-butyl dicarbonate (24424-99-5) + safranin O (477-73-6) → 7,7’-(2,2,17,17-tetramethyl-4,15-dioxo-3,16-dioxa-5,14-diazaoctadecane-5,14-diyl) bis(3-(tert-butoxycarbonylamino)-2,8-dimethyl-5-phenylphenazin-5-ium)chloride + 7-(tert-butoxycarbonyl(8-(tert-butoxycarbonyl(7-(tert-butoxycarbonylamino)-2,8-dimethyl-5-phenylphenazin-5-ium-3-yl)amino)octyl)amino)-3-(tert-butoxycarbonylamino)-2,6-dimethyl-5-phenylphenazin-5-ium dichloride

Conditions	Yield
Stage #1: safranin O With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 0.25h; Stage #2: di-tert-butyl dicarbonate In N,N-dimethyl-formamide at 20℃; for 2h; Stage #3: 1,8-diiodooctane Overall yield = 3 g; Further stages;
Stage #1: safranin O With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 0.25h; Stage #2: di-tert-butyl dicarbonate In N,N-dimethyl-formamide at 20℃; for 2h; Stage #3: 1,8-diiodooctane Overall yield = 3 g; Further stages;

di-tert-butyl dicarbonate (24424-99-5) + C20H19N4(1+)*Cl(1-) + safranin O (477-73-6) → 3,7-bis(tert-butoxycarbonylamino)-2,8-dimethyl-5-phenylphenazin-5-ium dichloride + 3,7-bis(tert-butoxycarbonylamino)-2,6-dimethyl-5-phenylphenazin-5-ium chloride

Conditions	Yield
Stage #1: C20H19N4(1+)*Cl(1-); safranin O With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 0.25h; Stage #2: di-tert-butyl dicarbonate In N,N-dimethyl-formamide at 20℃; for 2h; Overall yield = 5 g;
Stage #1: C20H19N4(1+)*Cl(1-); safranin O With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 0.25h; Stage #2: di-tert-butyl dicarbonate In N,N-dimethyl-formamide at 20℃; for 2h; Overall yield = 5 g;

1,8-diiodooctane (24772-63-2) + di-tert-butyl dicarbonate (24424-99-5) + C20H19N4(1+)*Cl(1-) + safranin O (477-73-6) → 7,7’-(octane-1,8-diylbis(azanediyl)) bis(3-amino-2,8-dimethyl-5-phenylphenazin-5-ium)chloride + 3-amino-7-(8-(7-amino-2,8-dimethyl-5-phenylphenazin-5-ium-3-ylamino)octylamino)-2,6-dimethyl-5-phenylphenazin-5-ium dichloride

Conditions	Yield
Stage #1: C20H19N4(1+)*Cl(1-); safranin O With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 0.25h; Stage #2: di-tert-butyl dicarbonate In N,N-dimethyl-formamide at 20℃; for 2h; Stage #3: 1,8-diiodooctane Overall yield = 2 g; Further stages;
Stage #1: C20H19N4(1+)*Cl(1-); safranin O With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 0.25h; Stage #2: di-tert-butyl dicarbonate In N,N-dimethyl-formamide at 20℃; for 2h; Stage #3: 1,8-diiodooctane Overall yield = 3 g; Further stages;

ethyl methyl ketone oxime (96-29-7) + bis(trichloromethyl) carbonate (32315-10-9) + safranin O (477-73-6) + bis(trifluoromethane)sulfonimide lithium (90076-65-6) → C30H33N6O4(1+)*C2F6NO4S2(1-)

Conditions	Yield
Stage #1: bis(trichloromethyl) carbonate; safranin O With triethylamine In acetonitrile at 20℃; for 4h; Stage #2: ethyl methyl ketone oxime In acetonitrile at 60℃; for 1h; Stage #3: bis(trifluoromethane)sulfonimide lithium In water; acetonitrile at 20℃; for 1h;	1.9 g

1,8-diiodooctane (24772-63-2) + di-tert-butyl dicarbonate (24424-99-5) + C20H19N4(1+)*Cl(1-) + safranin O (477-73-6) → 7,7’-(2,2,17,17-tetramethyl-4,15-dioxo-3,16-dioxa-5,14-diazaoctadecane-5,14-diyl) bis(3-(tert-butoxycarbonylamino)-2,8-dimethyl-5-phenylphenazin-5-ium)chloride + 7-(tert-butoxycarbonyl(8-(tert-butoxycarbonyl(7-(tert-butoxycarbonylamino)-2,8-dimethyl-5-phenylphenazin-5-ium-3-yl)amino)octyl)amino)-3-(tert-butoxycarbonylamino)-2,6-dimethyl-5-phenylphenazin-5-ium chloride

Conditions	Yield
Stage #1: C20H19N4(1+)*Cl(1-); safranin O With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 0.25h; Stage #2: di-tert-butyl dicarbonate In N,N-dimethyl-formamide at 20℃; for 2h; Stage #3: 1,8-diiodooctane Overall yield = 3 g; Further stages;

1,8-diiodooctane (24772-63-2) + di-tert-butyl dicarbonate (24424-99-5) + C20H19N4(1+)*Cl(1-) + safranin O (477-73-6) → 7,7’-(2,2,17,17-tetramethyl-4,15-dioxo-3,16-dioxa-5,14-diazaoctadecane-5,14-diyl) bis(3-(tert-butoxycarbonylamino)-2,8-dimethyl-5-phenylphenazin-5-ium)chloride + 7-(tert-butoxycarbonyl(8-(tert-butoxycarbonyl(7-(tert-butoxycarbonylamino)-2,8-dimethyl-5-phenylphenazin-5-ium-3-yl)amino)octyl)amino)-3-(tert-butoxycarbonylamino)-2,6-dimethyl-5-phenylphenazin-5-ium dichloride

Conditions	Yield
Stage #1: C20H19N4(1+)*Cl(1-); safranin O With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 0.25h; Stage #2: di-tert-butyl dicarbonate In N,N-dimethyl-formamide at 20℃; for 2h; Stage #3: 1,8-diiodooctane Overall yield = 3 g; Further stages;

cholic acid (81-25-4) + safranin O (477-73-6) → 3-amino-2,8-dimethyl-5-phenyl-7-yl-(N-(3α,7α,12α-trihydroxy-5β-cholan-24-amido))phenazin-5-ium chloride

Conditions	Yield
Stage #1: cholic acid; safranin O With dmap In dichloromethane; N,N-dimethyl-formamide for 0.166667h; Stage #2: With dicyclohexyl-carbodiimide In dichloromethane; N,N-dimethyl-formamide at 20℃;	83%

sodium hexachloroplatinate(IV) hexahydrate + carbon monoxide (201230-82-2) + safranin O (477-73-6) → 2((CH3)(H2N)C6H2)2N2C6H5(1+)*Pt12(CO)24(2-)=[((CH3)(H2N)C6H2)2N2C6H5]2[Pt12(CO)24]

Conditions	Yield
With sodium acetate In methanol Pt complex was added with stirring to soln. of CH3COONa in methanol under CO; after 24 h soln. of safranine in methanol was added; mixt. was stirred for 1 h; filtered; washed (methanol); dried (vac.); elem. anal.;	84%

safranin O (477-73-6) → 7,7‘-(hexane-1,6-diylbis(azanediyl)) bis(3-amino-2,8-dimethyl-5-phenylphenazin-5-ium)chloride

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / -40 °C 1.2: 1 h / -40 °C 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / -30 °C 2.2: 0.45 h / -30 - 20 °C 3.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 1 h / -40 °C 1.2: 1 h / -40 °C 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / -30 °C 2.2: 0.45 h / 0 - 20 °C 3.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 1 h / -40 °C 1.2: 1 h / -40 °C 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / -30 °C 2.2: 0.45 h / -30 - 20 °C 3.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 1 h / -40 °C 1.2: 1 h / -40 °C 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / -30 °C 2.2: 0.45 h / -30 - 20 °C 3.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 1 h / -40 °C 1.2: 1 h / -40 °C 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / -30 °C 2.2: 0.45 h / -40 - 20 °C 3.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C View Scheme

di-tert-butyl dicarbonate (24424-99-5) + safranin O (477-73-6) → tert-butyl N-(8-amino-3,7-dimethyl-10-phenyl-phenazin-10-ium-2-yl)-N-[6-[(8-amino-3,7-dimethyl-10-phenyl-phenazin-10-ium-2-yl)-tert-butoxycarbonyl-amino]hexyl]carbamate dichloride

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / -40 °C 1.2: 1 h / -40 °C 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / -30 °C 2.2: 0.45 h / -30 - 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 1 h / -40 °C 1.2: 1 h / -40 °C 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / -30 °C 2.2: 0.45 h / 0 - 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 1 h / -40 °C 1.2: 1 h / -40 °C 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / -30 °C 2.2: 0.45 h / -30 - 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 1 h / -40 °C 1.2: 1 h / -40 °C 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / -30 °C 2.2: 0.45 h / -30 - 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 1 h / -40 °C 1.2: 1 h / -40 °C 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / -30 °C 2.2: 0.45 h / -40 - 20 °C View Scheme

safranin O (477-73-6) → 3-((6-aminohexyl)(tert-butoxycarbonyl)amino)-7-(tert-butoxycarbonylamino)-2,8-dimethyl-5-phenylphenazin-5-ium chloride

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.25 h / 0 - 20 °C 1.2: 2 h / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 0.25 h / 20 °C 2.2: 16 h / 0 - 20 °C 3.1: hydrazine hydrate / ethanol / 1 h / 85 °C View Scheme
Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.25 h / 0 - 20 °C 1.2: 2 h / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 0.25 h / 20 °C 2.2: 16 h / 0 - 20 °C 3.1: hydrazine hydrate / ethanol / 1 h / 85 °C View Scheme
Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.25 h / 0 - 20 °C 1.2: 2 h / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 0.25 h / 20 °C 2.2: 16 h / 0 - 20 °C 3.1: hydrazine hydrate / ethanol / 1 h / 85 °C View Scheme

safranin O (477-73-6) → 3-(tert-butoxycarbonyl (6-(1,3-dioxoisoindolin-2-yl)hexyl)amino)-7-(tert-butoxycarbonylamino)-2,8-dimethyl-5-phenylphenazin-5-ium chloride

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.25 h / 0 - 20 °C 1.2: 2 h / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 0.25 h / 20 °C 2.2: 16 h / 0 - 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.25 h / 0 - 20 °C 1.2: 2 h / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 0.25 h / 20 °C 2.2: 16 h / 0 - 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.25 h / 0 - 20 °C 1.2: 2 h / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 0.25 h / 20 °C 2.2: 16 h / 0 - 20 °C View Scheme

safranin O (477-73-6) → 3-(tert-butoxycarbonyl (3-(1,3-dioxoisoindolin-2-yl)propyl)amino)-7-(tert-butoxycarbonylamino)-2,8-dimethyl-5-phenylphenazin-5-ium chloride

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.25 h / 0 - 20 °C 1.2: 2 h / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 0.25 h 2.2: 16 h / 0 - 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.25 h / 0 - 20 °C 1.2: 2 h / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 0.25 h / 20 °C 2.2: 16 h / 0 - 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.25 h / 0 - 20 °C 1.2: 2 h / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 0.25 h / 20 °C 2.2: 16 h / 0 - 20 °C View Scheme

safranin O (477-73-6) → 3-((3-aminopropyl)(tert-butoxycarbonyl)amino)-7-(tert-butoxycarbonylamino)-2,8-dimethyl-5-phenylphenazin-5-ium chloride

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.25 h / 0 - 20 °C 1.2: 2 h / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 0.25 h 2.2: 16 h / 0 - 20 °C 3.1: hydrazine hydrate / ethanol / 1 h / 85 °C View Scheme
Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.25 h / 0 - 20 °C 1.2: 2 h / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 0.25 h / 20 °C 2.2: 16 h / 0 - 20 °C 3.1: hydrazine hydrate / ethanol / 1 h / 85 °C View Scheme
Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.25 h / 0 - 20 °C 1.2: 2 h / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 0.25 h / 20 °C 2.2: 16 h / 0 - 20 °C 3.1: hydrazine hydrate / ethanol / 1 h / 85 °C View Scheme

safranin O (477-73-6) → 7,7’-(2,2,21,21-tetramethyl-4,19-dioxo-3,20-dioxa-5,18-diazadocosane-5,18-diyl) bis(3-(tert-butoxycarbonylamino)-2,8-dimethyl-5-phenylphenazin-5-ium)chloride

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.25 h / 0 - 20 °C 1.2: 2 h / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 0.25 h / 20 °C 2.2: 12 h / 0 - 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.25 h / 0 - 20 °C 1.2: 2 h / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 0.25 h / 20 °C 2.2: 12 h / 0 - 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.25 h / 0 - 20 °C 1.2: 2 h / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 0.25 h / 20 °C 2.2: 12 h / 0 - 20 °C View Scheme

safranin O (477-73-6) → [3-amino-7-({9-[(7-amino-5-chloranuide-2,8-dimethyl-5-phenyl-5λ6,10-phenazin-5-ylium-3-yl)amino]nonyl}amino)-2,8-dimethyl-5-phenyl-5λ6,10-phenazin-5-ylium-5-e]dichloranuide

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.25 h / 0 - 20 °C 1.2: 2 h / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 0.25 h / 20 °C 2.2: 12 h / 0 - 20 °C 2.3: 12 h / 0 - 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.25 h / 0 - 20 °C 1.2: 2 h / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 0.25 h / 20 °C 2.2: 12 h / 0 - 20 °C View Scheme

safranin O (477-73-6) → 7,7’-(2,2,18,18-tetramethyl-4,16-dioxo-3,17-dioxa-5,15-diazanonadecane-5,15-diyl) bis(3-(tert-butoxycarbonylamino)-2,8-dimethyl-5-phenylphenazin-5-ium)chloride

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.25 h / 0 - 20 °C 1.2: 2 h / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 0.25 h / 20 °C 2.2: 12 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.25 h / 0 - 20 °C 1.2: 2 h / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 0.25 h / 20 °C 2.2: 12 h / 0 - 20 °C View Scheme

safranin O (477-73-6) → 3-amino-7-(12-(7-amino-2,8-dimethyl-5-phenylphenazin-5-ium-3-ylamino)dodecylamino)-2,6-dimethyl-5-phenylphenazin-5-ium dichloride

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.25 h / 0 - 20 °C 1.2: 2 h / 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 0.25 h / 20 °C 2.2: 12 h / 0 - 20 °C View Scheme

Upstream product

• 3029-60-5 N,N'-dichloro-2-methyl-cyclohexa-2,5-diene-1,4-diylidenediamine 
• 6406-71-9 4-methyl-N¹-phenylbenzene-1,3-diamine 
• 95-70-5 2-methyl-p-phenylenediamine 
• 95-53-4 o-toluidine 

Downstream Products

• 4661-54-5 8-amino-3,7-dimethyl-10-phenyl-10H-phenazin-2-ylideneamine