128-80-3

Basic information

• Product Name: Solvent Green 3
• Synonyms: SOLVENT GREEN 3;SUDAN GREEN 4B;QUINIZARIN GREEN SS;QUINAZARINE GREEN BASE;QUINIZARIN GREEN;WAXOLINE GREEN G;1,4-bis((4-methylphenyl)amino)-10-anthracenedione;1,4-bis((4-methylphenyl)amino)-9,10-anthracenedione
• CAS NO: 128-80-3
• Molecular Formula: C₂₈H₂₂N₂O₂
• Molecular Weight: 418.49
• EINECS: 204-909-5
• Product Categories: Aminoanthraquinones;Anthraquinones;Solvent Dyestuff;Solvent Dye
• Mol File: 128-80-3.mol
• Article Data: 4

Chemical Properties

• Melting Point: 220-221 °C
• Boiling Point: 536.24°C (rough estimate)
• Flash Point: 197 °C
• Appearance: black fine crystalline powder
• Density: 1.1816 (rough estimate)
• Vapor Pressure: 5.73E-16mmHg at 25°C
• Refractive Index: 1.5800 (estimate)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: Acetone (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: -0.02±0.20(Predicted)
• Water Solubility: 10μg/L at 25℃
• Merck: 14,8065
• CAS DataBase Reference: Solvent Green 3(CAS DataBase Reference)
• NIST Chemistry Reference: Solvent Green 3(128-80-3)
• EPA Substance Registry System: Solvent Green 3(128-80-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-22-26
• WGK Germany: 2
• RTECS: CB5775000
• Hazardous Substances Data: 128-80-3(Hazardous Substances Data)

Usage

Chemical Properties

Solvent Green 3 is black fine crystalline powder

Uses

Solvent Green 3 used in externally applied drugs and cosmetics: ibid. 47, 14138 (1982).

Preparation

1,4-Dihydroxyanthracene-9,10-dione and to p-Methylaniline (2 Moore) condensation.

Flammability and Explosibility

Notclassified

Properties and Applications

blue light green. And C.I. Solvent Green 3 the same chemical structure.

InChI:InChI=1/C28H22N2O2/c1-17-7-11-19(12-8-17)29-23-15-16-24(30-20-13-9-18(2)10-14-20)26-25(23)27(31)21-5-3-4-6-22(21)28(26)32/h3-16,29-30H,1-2H3

Synthetic route

1,4-dihydroxy-9,10-anthracenedione (81-64-1) + p-toluidine (106-49-0) → D and C green 6 (128-80-3)

Conditions	Yield
With leucoquinizarin; boric acid; sodium hydrogensulfite In ethanol; benzene at 62 - 66℃; for 12h; Temperature; Solvent;	97%
With 1-butyl-3-ethyl-1H-imidazolium tetrafluoroborate at 85 - 125℃; Reagent/catalyst; Temperature; Green chemistry; Large scale;	95.9%
With boric acid; calcium carbonate; tin(ll) chloride at 110 - 130℃;

1,4-dichloroanthraquinone (602-25-5) + p-toluidine (106-49-0) → D and C green 6 (128-80-3)

Conditions	Yield
With potassium phosphate In ethylbenzene at 150℃; for 6h;	90%
at 190℃;

1,4-dimethoxyanthraquinone (6119-74-0) + p-toluidine (106-49-0) → D and C green 6 (128-80-3)

9,10-Dihydroxy-2,3-dihydro-anthracene-1,4-dione (17648-03-2) + p-toluidine (106-49-0) → D and C green 6 (128-80-3)

Conditions	Yield
With boric acid
With 1,4-dihydroxy-9,10-anthracenedione

1,4-diamino-9,10-anthraquinone (128-95-0) + p-toluidine (106-49-0) → D and C green 6 (128-80-3)

Conditions	Yield
With tin(ll) chloride

1,4-diamino-anthracene-9,10-diol (5327-72-0) + p-toluidine (106-49-0) → D and C green 6 (128-80-3)

Conditions	Yield
Erhitzen unter Luftzutritt auf 150grad;

1-chloro-4-dimethylamino-anthraquinone (117499-93-1) + p-toluidine (106-49-0) → 1-(methylamino)-4-[(4-methylphenyl)amino]anthraquinone (128-85-8) + D and C green 6 (128-80-3)

Conditions	Yield
at 180℃;

1-Nitro-4-chloroanthraquinone (6337-82-2) + p-toluidine (106-49-0) → D and C green 6 (128-80-3)

Conditions	Yield
With boric acid; sodium carbonate; tin(ll) chloride

1-methoxy-4-nitro-anthraquinone (81-66-3) + p-toluidine (106-49-0) → D and C green 6 (128-80-3)

Conditions	Yield
at 160 - 180℃;

1-methoxy-4-phenoxy-anthraquinone (80490-02-4) + p-toluidine (106-49-0) → D and C green 6 (128-80-3)

1-bromo-4-methoxy-anthraquinone (861083-48-9) + sodium acetate (127-09-3) + p-toluidine (106-49-0) → D and C green 6 (128-80-3)

Conditions	Yield
at 180 - 190℃;

1-bromo-4-methoxy-anthraquinone (861083-48-9) + p-toluidine (106-49-0) → D and C green 6 (128-80-3)

Conditions	Yield
With sodium acetate at 180 - 190℃;

9,10-Dihydroxy-2,3-dihydro-anthracene-1,4-dione (17648-03-2) + metaboric acid (13460-50-9) + p-toluidine (106-49-0) → D and C green 6 (128-80-3)

Conditions	Yield
giesst das Reaktionsprodukt in verd. Salzsaeure;

1,4-dihydroxy-9,10-anthracenedione (81-64-1) + 9,10-Dihydroxy-2,3-dihydro-anthracene-1,4-dione (17648-03-2) + metaboric acid (13460-50-9) + p-toluidine (106-49-0) → D and C green 6 (128-80-3)

Conditions	Yield
at 110 - 130℃;
at 110 - 130℃;

metaboric acid (13460-50-9) + p-toluidine (106-49-0) + quinizarine (1/2 mol) → D and C green 6 (128-80-3)

Conditions	Yield
at 130 - 140℃;

p-toluidine (106-49-0) + quinizarinedimethyl ether → D and C green 6 (128-80-3)

p-toluidine (106-49-0) + quinizarinediethyl ether → D and C green 6 (128-80-3)

1,4-diamino-9,10-anthraquinone (128-95-0) + p-toluidine (106-49-0) + tin dichloride → D and C green 6 (128-80-3)

1-chloro-4-dimethylamino-anthraquinone (117499-93-1) + p-toluidine (106-49-0) → D and C green 6 (128-80-3) + 1-monomethylamino-4-p-toluidino-anthraquinone

Conditions	Yield
at 180℃;

1-methoxyanthracene-9,10-dione (82-39-3) → D and C green 6 (128-80-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: nitric acid View Scheme
Multi-step reaction with 2 steps 1: water / beim Bromieren 2: sodium acetate / 180 - 190 °C View Scheme
Multi-step reaction with 2 steps 1: water / beim Bromieren 2: 180 - 190 °C View Scheme

1-chloroanthracene-9,10-dione (82-44-0) → D and C green 6 (128-80-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: HNO3+H2SO4 2: tin dichloride; sodium carbonate; boric acid View Scheme

1-methoxy-4-nitro-anthraquinone (81-66-3) → D and C green 6 (128-80-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 110 - 120 °C View Scheme

1,4-dihydroxy-9,10-anthracenedione (81-64-1) + p-toluidine (106-49-0) → 1-hydroxy-4-(4-methylphenylamino)-9,10-anthraquinone (81-48-1) + D and C green 6 (128-80-3)

Conditions	Yield
With LACTIC ACID; Trimethyl borate; 2,3-dihydro-1,4-dihydroxyanthraquinone In 4-butanolide at 100℃; for 13h; Product distribution / selectivity;
With LACTIC ACID; 2,3-dihydro-1,4-dihydroxyanthraquinone; boric acid In 4-butanolide at 100 - 125℃; for 19h; Product distribution / selectivity;

D and C green 6 (128-80-3) → 1,4-bis(4-methyl-2-bromophenyl)aminoanthraquinone

Conditions	Yield
With sulfuric acid; bromine at 25℃; for 40h;	100%
With bromine In tetrachloromethane at 3 - 5℃; Temperature;	95.1%

D and C green 6 (128-80-3) → 1,4-bis-(4-methyl-2-nitro-anilino)-anthraquinone (75839-23-5)

Conditions	Yield
With nitric acid In acetic acid at 20 - 60℃; for 2h;	95.7%
With acetic acid; sodium nitrite

D and C green 6 (128-80-3) → solvent violet 38

Conditions	Yield
With bromine In tetrachloromethane at 60℃; for 3h;	81.4%

D and C green 6 (128-80-3) + sodium cyanide (143-33-9) → 9,10-Dioxo-9,10-dihydro-1,4-bis(p-tolylamino)anthracen-2,3-dicarbonitril

Conditions	Yield
With ammonium bicarbonate 1.) DMSO, 100 deg C, 15 h; 2.) water, r.t., 4 h;	50%

D and C green 6 (128-80-3) → quinizarin green (3443-90-1)

Conditions	Yield
With sulfuric acid at 70 - 80℃;
With sulfuric acid at 70 - 80℃;

D and C green 6 (128-80-3) → 4-(9,10-dioxo-4-p-toluidino-9,10-dihydro-[1]anthrylamino)-toluene-3-sulfonic acid (3179-85-9)

Conditions	Yield
With sulfuric acid at 70 - 80℃;
With sulfuric acid at 70 - 80℃;

D and C green 6 (128-80-3) → 8-(p-Toluidino)-2-methylceramidonine (7628-56-0)

Conditions	Yield
With PPA at 130℃; for 3h;
With sulfuric acid at 120 - 130℃; for 3h;	1.4 g
With sulfuric acid at 0 - 125℃; for 11h;	9.2 g
With sulfuric acid at 140 - 150℃;

D and C green 6 (128-80-3) → 3,6-di-p-tolyl-2,3,6,7-tetrahydro-anthra[1,9-de;4,10-d'e']bis[1,3]oxazine

D and C green 6 (128-80-3) → 1,4-di(3-nitro-4-methylanilino)anthraquinone (75839-44-0)

Conditions	Yield
Yield given. Multistep reaction;

D and C green 6 (128-80-3) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → C34H34N4O2(2+)*2Cl(1-)

Conditions	Yield
With trichlorophosphate In ethanethiol for 0.5h;

sulfuric acid (7664-93-9) + D and C green 6 (128-80-3) → quinizarin green (3443-90-1)

Upstream product

• 81-64-1 1,4-dihydroxy-9,10-anthracenedione 
• 106-49-0 p-toluidine 
• 81-66-3 1-methoxy-4-nitro-anthraquinone 
• 82-39-3 1-methoxyanthracene-9,10-dione 
• 117499-93-1 1-chloro-4-dimethylamino-anthraquinone 
• 128-95-0 1,4-diamino-9,10-anthraquinone 
• 13460-50-9 metaboric acid 
• 17648-03-2 9,10-Dihydroxy-2,3-dihydro-anthracene-1,4-dione 
• 861083-48-9 1-bromo-4-methoxy-anthraquinone 
• 127-09-3 sodium acetate 
• 80490-02-4 1-methoxy-4-phenoxy-anthraquinone 
• 6337-82-2 1-Nitro-4-chloroanthraquinone 
• 5327-72-0 1,4-diamino-anthracene-9,10-diol 
• 6119-74-0 1,4-dimethoxyanthraquinone 

Downstream Products

• 3443-90-1 quinizarin green 
• 3179-85-9 4-(9,10-dioxo-4-p-toluidino-9,10-dihydro-[1]anthrylamino)-toluene-3-sulfonic acid 
• 75839-23-5 1,4-bis-(4-methyl-2-nitro-anilino)-anthraquinone 
• 7628-56-0 8-(p-Toluidino)-2-methylceramidonine 
• 63512-14-1 solvent violet 38 
• 201941-71-1 [Pt₂(P(C₂H₅)3)2Cl₂(C₆H₄(CO)2C₆H₂(NC₆H₄CH₃)2)] 
• 201941-72-2 [Pd₂(P(C₂H₅)3)2Cl₂(C₆H₄(CO)2C₆H₂(NC₆H₄CH₃)2)] 
• 74634-23-4 1,4-di(3-bromo-4-methylanilino)anthraquinone 
• 75839-44-0 1,4-di(3-nitro-4-methylanilino)anthraquinone 

Relevant articles and documents

Method for catalytically synthesizing N-aryl/alkyl anthraquinone and derivatives thereof by using carbene metal ligand

The invention discloses a method for catalytically synthesizing N-aryl/alkyl anthraquinone and derivatives thereof by using a carbene metal ligand. The method for catalytically synthesizing the N-aryl/alkyl anthraquinone and the derivatives thereof by using the carbene metal ligand provided by the invention comprises the following steps: with the carbene metal ligand and alkali as catalysts and anthraquinone compounds and primary amine compounds as raw materials, allowing the anthraquinone compounds and the primary amine compounds to react in an organic solvent at 100-150 DEG C for 2-12 hours;cooling a reaction liquid after the reaction is finished, and carrying out rotary evaporation so as to remove the solvent; purifying a crude product through a silicon dioxide column, and carrying outeluting with petroleum ether/dichloromethane so as to obtain pure N-aryl/alkyl anthraquinone and derivatives thereof. According to the invention, the selectivity of a tetra-substituted target productis improved and is 90% or above; byproducts are few, and the separation cost of a product is reduced; the reaction is carried out in the organic solvent without water and oxyge;, simple reaction conditions and easy operation are achieved; and industrial production is facilitated.

A solvent green 3 synthetic method (by machine translation)

The invention discloses a solvent green 3 synthetic method, in order to 1, 4 - dihydroxy anthraquinone and P-toluidine as raw materials, using ethanol as solvent, boric acid as catalyst, 1, 4 - dihydroxy anthraquinone leuco body is initiator, sodium bisulfite as antioxidant, benzene as the system of the entrainer, by condensation reaction to obtain the target product. This invention adopts the low boiling point alcohol as solvent, solvent green 3 almost insoluble in ethanol, not only improves the yield of products, also reduces the solvent recovery energy consumption; the 1, 4 - dihydroxy anthraquinone leuco as initiator, not only has the role of the initiator of the reaction, the reaction process also play a role in catalysis, in the presence of antioxidant is sodium bisulfite, can ensure the 1, 4 - dihydroxy anthraquinone leuco activity, initiating and catalytic action is improved. (by machine translation)