81-39-0

Basic information

• Product Name: Solvent Red 52
• Synonyms: 3H-Naphtho1,2,3-dequinoline-2,7-dione, 3-methyl-6-(4-methylphenyl)amino-;3-methyl-6-[(4-methylphenyl)amino]-3H-Dibenz[f,ij]isoquinoline-2,7-dione;abcol red 5b;Solvent red 52 (C.I. 68210);C.I.68210;3H-Naphtho[1, 2, 3-de]quinoline-2, 7-dione, 2-methyl-6-[(4-methylphenyl)amino];Amarsol Red 5B;Elbaplast Red 5B
• CAS NO: 81-39-0
• Molecular Formula: C₂₄H₁₈N₂O₂
• Molecular Weight: 366.41
• EINECS: 201-346-7
• Product Categories: Solvent Dyestuff
• Mol File: 81-39-0.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 585 °C at 760 mmHg
• Flash Point: 307.6 °C
• Appearance: /
• Density: 1.36 g/cm³
• Vapor Pressure: 1.14E-13mmHg at 25°C
• Refractive Index: 1.729
• PKA: 0.46±0.20(Predicted)
• Water Solubility: 750-2880900ng/L at 20-30℃
• CAS DataBase Reference: Solvent Red 52(CAS DataBase Reference)
• NIST Chemistry Reference: Solvent Red 52(81-39-0)
• EPA Substance Registry System: Solvent Red 52(81-39-0)

Safety Data

• Hazardous Substances Data: 81-39-0(Hazardous Substances Data)

Usage

Uses

Solvent Red 52 is used in method for production of Poly(trimethylene furandicarboxylate) using Zinc catalyst.

Preparation

(a) 6-Bromo-3-methyl-3H-naphtho[1,2,3-de]quinoline-2,7-dione or 1-Bromo-4-(N-methylacetamido)anthraquinone and p-Methylaniline condensation; (b)N-(4-(p-toluidino)-9,10-dioxo-9,10-dihydroanthracen-1-yl)-N-methylacetamide closed loop into Anthrapyridone.

Properties and Applications

blue light red. Soluble in water and Pyridine . In concentrated sulfuric acid for deep red, red precipitation after dilution. Used for acetate, polyethylene, thermal plastic coloring.

InChI:InChI=1/C24H18N2O2/c1-14-7-9-15(10-8-14)25-19-11-12-20-22-18(13-21(27)26(20)2)16-5-3-4-6-17(16)24(28)23(19)22/h3-13,25H,1-2H3

Synthetic route

6-hydroxy-3-methyl-3H-naphtho[1,2,3-de]quinoline-2,7-dione (2582-20-9) + p-toluidine (106-49-0) → 6-(p-Tolylamino)-N-methylanthrapyridone (81-39-0)

Conditions	Yield
With boric acid at 100 - 120℃; Large scale; Green chemistry;	97.5%

6-bromo-N-methylanthrapyridone (81-85-6) + p-toluidine (106-49-0) → 6-(p-Tolylamino)-N-methylanthrapyridone (81-39-0)

Conditions	Yield
With potassium acetate at 165℃;
With sodium acetate at 160 - 170℃;

3-methyl-6-nitro-3H-naphtho[1,2,3-de]quinoline-2,7-dione (873418-99-6) + p-toluidine (106-49-0) → 6-(p-Tolylamino)-N-methylanthrapyridone (81-39-0)

Conditions	Yield
With copper diacetate; sodium acetate at 160 - 175℃;

1-(acetyl-methyl-amino)-4-p-toluidino-anthraquinone (6535-64-4) → 6-(p-Tolylamino)-N-methylanthrapyridone (81-39-0)

Conditions	Yield
With sodium methylate

p-toluidine (106-49-0) + 1'-methyl-4-methoxy-anthrapyridone → 6-(p-Tolylamino)-N-methylanthrapyridone (81-39-0)

3-methyl-2,3-dihydro-7H-dibenzisoquinoline-2,7-dione (2582-19-6) → 6-(p-Tolylamino)-N-methylanthrapyridone (81-39-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: water; nitric acid 2: sodium acetate; copper (II)-acetate / 160 - 175 °C View Scheme

1-(acetyl-methyl-amino)-anthraquinone (75507-40-3) → 6-(p-Tolylamino)-N-methylanthrapyridone (81-39-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: water; KOH-solution; 2-ethoxy-ethanol 2: water; nitric acid 3: sodium acetate; copper (II)-acetate / 160 - 175 °C View Scheme

6-(p-Tolylamino)-N-methylanthrapyridone (81-39-0) → 2,8-Dimethyl-8H-benzonaphtho<1,2,3,4-lmn><4, 7>phenanthrolin-9-one (92629-03-3)

Conditions	Yield
With PPA at 175 - 180℃; for 6h;	99%
With sulfuric acid at 170℃;

6-(p-Tolylamino)-N-methylanthrapyridone (81-39-0) + acetic anhydride (108-24-7) → N-(3-methyl-2,7-dioxo-2,7-dihydro-3H-naphtho[1,2,3-de]quinolin-6-yl)-N-p-tolyl-acetamide (101611-82-9)

Conditions	Yield
With zinc(II) chloride

6-(p-Tolylamino)-N-methylanthrapyridone (81-39-0) → 3-methyl-6-(4-methyl-2-nitro-anilino)-3H-naphtho[1,2,3-de]quinoline-2,7-dione

Conditions	Yield
With nitric acid

6-(p-Tolylamino)-N-methylanthrapyridone (81-39-0) → 3-methyl-6-p-tolyl-3,6-dihydro-dibenzo[f,lmn][2,9]phenanthroline-2,7-dione (101812-37-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: ZnCl2 2: KOH View Scheme

Upstream product

• 2582-20-9 6-hydroxy-3-methyl-3H-naphtho[1,2,3-de]quinoline-2,7-dione 
• 106-49-0 p-toluidine 
• 2582-19-6 3-methyl-2,3-dihydro-7H-dibenzisoquinoline-2,7-dione 
• 6535-64-4 1-(acetyl-methyl-amino)-4-p-toluidino-anthraquinone 
• 873418-99-6 3-methyl-6-nitro-3H-naphtho[1,2,3-de]quinoline-2,7-dione 
• 81-85-6 6-bromo-N-methylanthrapyridone 
• 75507-40-3 1-(acetyl-methyl-amino)-anthraquinone 

Downstream Products

• 101812-37-7 3-methyl-6-p-tolyl-3,6-dihydro-dibenzo[f,lmn][2,9]phenanthroline-2,7-dione 
• 101611-82-9 1'-Methyl-4-(N-acetyl-p-toluidino)-anthrapyridon 

Relevant articles and documents

Environment-friendly synthesis method of anthrapyridone dye

The invention relates to an environment-friendly synthesis method of anthrapyridone dye. The method comprises the following steps: (1) adding ethyl acetate, monomethylamine and a phase transfer catalyst sequentially to a pressure vessel, and performing stirring for dissolution so as to obtain a first mixture; (2) heating the first mixture to 80-110 DEG C for a reaction, then performing cooling to40-70 DEG C, proceeding the reaction, performing pressure relief, determining the terminal point of the reaction, and performing cooling and filtration so as to obtain an intermediate A; (3) adding DMF, 1,4-dihydroxy anthraquinone and an auxiliary agent to the intermediate A, performing heating to 130-150 DEG C for a reaction, then performing cooling to 30-40 DEG C, and performing filtration so asto obtain an intermediate B; and (4) adding aromatic amine or alicyclic amine to the intermediate B, and performing a condensation reaction in the presence of boric acid until the terminal point. Through implementation of the environment-friendly synthesis method of anthrapyridone dye, good economic, social and ecologically environmental benefits can be achieved.