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Basic Red 2

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Name

Basic Red 2

EINECS 207-518-8
CAS No. 477-73-6 Density 1.00 g/mL at 20 °C
PSA 68.81000 LogP 1.61230
Solubility Soluble in water Melting Point >240℃ (decompose)
Formula C20H19ClN4 Boiling Point 507.14°C (rough estimate)
Molecular Weight 350.851 Flash Point 46 °C
Transport Information UN 1170 3/PG 3 Appearance Dark red to violet powder
Safety 26-39-24/25-36-16 Risk Codes 41-10-36/37/38
Molecular Structure Molecular Structure of 477-73-6 (Basic Red 2) Hazard Symbols IrritantXi
Synonyms

C.I. Basic Red 2;Phenazinium, 3,7-diamino-2,8-dimethyl-5-phenyl-, chloride (9CI);Safranine T;2,8-Dimethylphenosafranine;3,7-Diamino-2,8-dimethyl-5-phenylphenazinium chloride;Basic Pink;Brilliant Safranine BR;Brilliant Safranine GR;C.I.50240;Calcozine Red Y;Duasyn Basic Red TH;Hidaco Safranine;Leather Red HT;Mitsui Safranine T;NipponKagaku Safranine GK;Nippon Kagaku Safranine T;Safranin;Safranin O;Safranine G;Tolusafranine;

 

Basic Red 2 Synthetic route

95-53-4

o-toluidine

477-73-6

safranin O

Conditions
ConditionsYield
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

10-phenyl-3-acetylamino-2,7-dimethyl-phenazinium chloride

ammonia

ammonia

477-73-6

safranin O

Conditions
ConditionsYield
With ethanol
95-70-5

2-methyl-p-phenylenediamine

477-73-6

safranin O

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

477-73-6

safranin O

Conditions
ConditionsYield
With ethanol
4549-32-0

1,8-dibromooctane

477-73-6

safranin O

Conditions
ConditionsYield
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;
24424-99-5

di-tert-butyl dicarbonate

477-73-6

safranin O

3-amino-7-(tert-butoxy carbonylamino)-2,8-dimethyl-5-phenylphenazin-5-ium chloride

Conditions
ConditionsYield
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
540-72-7

sodium thiocyanide

477-73-6

safranin O

7-amino-2,8-dimethyl-3-thiocyanato-5-phenyl-phenazinium tetrafluoroborate

Conditions
ConditionsYield
With tetrafluoroboric acid; sodium nitrite In water at 50 - 60℃; for 2h;64%
477-73-6

safranin O

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
ConditionsYield
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
477-73-6

safranin O

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
ConditionsYield
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
24424-99-5

di-tert-butyl dicarbonate

477-73-6

safranin O

A

3,7-bis(tert-butoxycarbonylamino)-2,8-dimethyl-5-phenylphenazin-5-ium dichloride

B

3,7-bis(tert-butoxycarbonylamino)-2,6-dimethyl-5-phenylphenazin-5-ium chloride

Conditions
ConditionsYield
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;

Basic Red 2 Consensus Reports

Reported in EPA TSCA Inventory.

Basic Red 2 Specification

The Basic Red 2, with the CAS registry number 477-73-6, is also known as Safranin O. It belongs to the product categories of S; Stains and Dyes; Stains & Dyes. Its EINECS number is 207-518-8. This chemical's molecular formula is C20H19ClN4 and molecular weight is 350.84. What's more, its systematic name is 3,7-Diamino-2,8-dimethyl-5-phenylphenazin-5-ium chloride. Its classification codes are: (1)Antineoplastic agents; (2)Coloring Agents; (3)Indicators and reagents; (4)Mutation data. This chemical should be sealed and stored in a ventilated and dry place. Moreover, it should be protected from oxides. This chemical is a biological stain used in histology and cytology. It is used as a counterstain in some staining protocols, colouring all cell nuclei red. This is the classic counterstain in a Gram stain. It can also be used for the detection of cartilage, mucin and mast cell granules. It is mainly used as oxidation-reduction [redox] and acid-base indicator. It is obtained by the joint oxidation of one molecule of a para-diamine with two molecules of a primary amine; by the condensation of para-aminoazo compounds with primary amines, and by the action of para-nitrosodialkylanilines with secondary bases such as diphenylmetaphenylenediamine.

Physical properties of Basic Red 2 are: (1)#H bond acceptors: 4; (2)#H bond donors: 4; (3)#Freely Rotating Bonds: 3; (4)Polar Surface Area: 23.25 Å2.

When you are using this chemical, please be cautious about it as the following:
This chemical is flammable, so you should keep it away from sources of ignition - No smoking. It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you must avoid contact with skin and eyes and wear suitable protective clothing and eye/face protection.

You can still convert the following datas into molecular structure:
(1)SMILES: [Cl-].n1c4c([n+](c2c1cc(c(N)c2)C)c3ccccc3)cc(c(c4)C)N
(2)Std. InChI: InChI=1S/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
(3)Std. InChIKey: OARRHUQTFTUEOS-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intravenous 24020ug/kg (24.02mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION
Stanford Medical Bulletin. Vol. 9, Pg. 96, 1951.
mouse LDLo oral 1600mg/kg (1600mg/kg)   Journal of Pharmaceutical Sciences. Vol. 69, Pg. 327, 1980.
rabbit LD50 intravenous 26940ug/kg (26.94mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION
Stanford Medical Bulletin. Vol. 9, Pg. 96, 1951.
rat LD50 intravenous 28740ug/kg (28.74mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Stanford Medical Bulletin. Vol. 9, Pg. 96, 1951.

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