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

Chemical Properties

Dark red to violet powder

Uses

Different sources of media describe the Uses of 477-73-6 differently. You can refer to the following data:
1. A biological stain used to stain Gram negative bacteria, chromosomes, mucin, cartilage and mast cells. Dyes and metabolites, Environmental Testing
2. In forensics to visualize details of cyanoacrylate-fumed friction ridges of human digits.

Definition

A red dye that flu- oresces when exposed to selected wavelengths of light.

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.

Properties and Applications

bright blue light pink. Soluble in water for red, soluble in ethanol with yellow red fluorescent red. The strong sulfuric acid for green, diluted by blue to become red. The dye solution to join sodium hydroxide produce light brown red precipitate; Join the hydrochloric acid into blue purple. Used for paper making industry and color up manufacturing. Also used in acrylic, linen, silk products dyeing. Standard( Cotton ) Light Fastness Persperation Fastness Ironing Fastness Soaping Fading Stain Fading Stain Fading Stain C 1-2 2 2-3 2-3 5

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 
• 95-53-4 o-toluidine 
• 95-70-5 2-methyl-p-phenylenediamine 

Downstream Products

• 7006-08-8 C₂₀H₁₉N₄