4051-63-2

Basic information

• Product Name: Pigment Red 177
• Synonyms: C.I. 65300;4,4'-diamino-[1,1'-bianthracene]-9,9',10,10'-tetraone;pigment red 177;1,1-Bianthracene-9,9,10,10-tetrone, 4,4-diamino-;ANTHRAQUINONE RED;Pigment red 177 (C.I. 65300);Fast Red A3B;C.I. Pigment Red 177
• CAS NO: 4051-63-2
• Molecular Formula: C₂₈H₁₆N₂O₄
• Molecular Weight: 444.43764
• EINECS: 223-754-4
• Mol File: 4051-63-2.mol
• Article Data: 5

Chemical Properties

• Melting Point: 356-358°C
• Boiling Point: 797.2 °C at 760 mmHg
• Flash Point: 435.9 °C
• Appearance: /
• Density: 1.488
• Vapor Pressure: 2.03E-25mmHg at 25°C
• Refractive Index: 1.77
• PKA: -0.63±0.20(Predicted)
• Water Solubility: 25μg/L at 20-23℃
• CAS DataBase Reference: Pigment Red 177(CAS DataBase Reference)
• NIST Chemistry Reference: Pigment Red 177(4051-63-2)
• EPA Substance Registry System: Pigment Red 177(4051-63-2)

Safety Data

• Hazardous Substances Data: 4051-63-2(Hazardous Substances Data)

Usage

Properties and Applications

TEST ITEMS SPECIFICATION APPEARANCE RED POWDER SHADE BLUISH (REDDISH THAN A3B) HEAT RESISTANCE 300°C min LIGHT FASTNESS 7-8 ACID RESISTANCE 5 ALKALI RESISTANCE 5 FASTNESS TO BLEEDING 5 OIL ABSORPTION 35-40% SPECIFIC SURFACE 27 m 2 /g DENSITY 1.60 g/cm 3 RESIDUE ON 80 MESH 5.0% max WATER SOLUBLE 1.0% max VOLATITE 105 °C 1.0% max TINTING STRENGTH 100-105 %

TEST ITEMS

SPECIFICATION

APPEARANCE

RED POWDER

SHADE

BLUISH (REDDISH THAN A3B)

HEAT RESISTANCE

300°C min

LIGHT FASTNESS

7-8

ACID RESISTANCE

5

ALKALI RESISTANCE

5

FASTNESS TO BLEEDING

5

OIL ABSORPTION

35-40%

SPECIFIC SURFACE

27 m 2 /g

DENSITY

1.60 g/cm 3

RESIDUE ON 80 MESH

5.0% max

WATER SOLUBLE

1.0% max

VOLATITE 105 °C

1.0% max

TINTING STRENGTH

100-105 %

InChI:InChI=1/C28H16N2O4/c29-19-11-9-13(21-23(19)27(33)17-7-3-1-5-15(17)25(21)31)14-10-12-20(30)24-22(14)26(32)16-6-2-4-8-18(16)28(24)34/h1-12H,29-30H2

Synthetic route

disodium 4,4'-diamino-1,1'-bianthraquinonyl-3,3'-disulfonate (6022-22-6) → 4,4'-diamino-[1,1'-bianthracene]-9,9',10,10'-tetraone (4051-63-2)

Conditions	Yield
With 1-(4-sulfonylbutyl)pyridinium trifluoromethanesulfonate at 110 - 140℃; for 6.25h; Reagent/catalyst; Temperature;	98.22%
With sulfuric acid at 160℃; for 3.5h;

4,4'-diamino-1,1'-dianthraquinonyl-3,3'-disulfonic acid (69166-06-9) → 4,4'-diamino-[1,1'-bianthracene]-9,9',10,10'-tetraone (4051-63-2)

Conditions	Yield
With 1-(n-butyl)-3-methylimidazolium triflate at 140℃; for 11h; Temperature; Ionic liquid;	97.9%
With sodium hydroxide; D-glucose

1-Nitro-4-chloroanthraquinone (6337-82-2) → 4,4'-diamino-[1,1'-bianthracene]-9,9',10,10'-tetraone (4051-63-2)

Conditions	Yield
With copper Reduktion des Produkts;

4,4'-Dibenzoylamino-1,1'-bianthraquinonyl (94117-83-6) → 4,4'-diamino-[1,1'-bianthracene]-9,9',10,10'-tetraone (4051-63-2)

Conditions	Yield
With sulfuric acid at 90 - 100℃; Yield given;

1-benzamido-4-chloroanthraquinone (81-45-8) → 4,4'-diamino-[1,1'-bianthracene]-9,9',10,10'-tetraone (4051-63-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 76 percent / Copper powder / dimethylformamide / 1.5 h / Heating 2: conc.H2SO4 / 90 - 100 °C View Scheme

1-amino-4-bromo-9,10-dioxoanthracene-2-sulphonic acid (116-81-4) → 4,4'-diamino-[1,1'-bianthracene]-9,9',10,10'-tetraone (4051-63-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: aqueous alkaline solution; copper 2: aq. NaOH solution; D-glucose View Scheme

4,4'-diamino-[1,1'-bianthracene]-9,9',10,10'-tetraone (4051-63-2) + benzoyl chloride (98-88-4) → 4,4'-Dibenzoylamino-1,1'-bianthraquinonyl (94117-83-6)

Conditions	Yield
With nitrobenzene at 180℃;

C9H13ClN2O3 + 4,4'-diamino-[1,1'-bianthracene]-9,9',10,10'-tetraone (4051-63-2) → C37H28N4O7 (847453-73-0)

Conditions	Yield
In dimethyl sulfoxide at 80℃; for 6h; Heating / reflux;

C15H15ClN2O3 (847453-81-0) + 4,4'-diamino-[1,1'-bianthracene]-9,9',10,10'-tetraone (4051-63-2) → C43H30N4O7

Conditions	Yield
In dimethyl sulfoxide at 120℃; for 12h;
In dimethyl sulfoxide at 120℃; for 12h;

C18H35NO2 (677798-25-3) + 4,4'-diamino-[1,1'-bianthracene]-9,9',10,10'-tetraone (4051-63-2) → C46H49N3O5 (677798-31-1)

Conditions	Yield
Stage #1: C18H35NO2 With thionyl chloride In dimethyl sulfoxide at 20℃; for 1h; Stage #2: 4,4'-diamino-[1,1'-bianthracene]-9,9',10,10'-tetraone In dimethyl sulfoxide at 80℃; for 6h;

1,3,5-trichloro-2,4,6-triazine (108-77-0) + 4,4'-diamino-[1,1'-bianthracene]-9,9',10,10'-tetraone (4051-63-2) → C34H14Cl4N8O4 (98809-03-1)

Conditions	Yield
In 1,4-dioxane at 100℃; for 10h;

2-Ethylhexylamine (104-75-6) + 4,4'-diamino-[1,1'-bianthracene]-9,9',10,10'-tetraone (4051-63-2) → C66H86N12O4 (1227678-81-0)

Conditions	Yield
In 1,4-dioxane for 7h; Reflux;

4,4'-diamino-[1,1'-bianthracene]-9,9',10,10'-tetraone (4051-63-2) + 3-cyclohexylpropionyl chloride (39098-75-4) → C46H44N2O6 (1228443-08-0)

Conditions	Yield
In chlorobenzene for 3h; Reflux;

4,4'-diamino-[1,1'-bianthracene]-9,9',10,10'-tetraone (4051-63-2) + 4-diphenylsulfonyl chloride (1623-93-4) → C52H32N2O8S2 (1228443-12-6)

Conditions	Yield
In dichlorobenzene, 1,2- at 185℃; for 6h;

cyclopentanepropanoyl chloride (104-97-2) + 4,4'-diamino-[1,1'-bianthracene]-9,9',10,10'-tetraone (4051-63-2) → C44H40N2O6 (1281462-05-2)

Conditions	Yield
In chlorobenzene at 180℃; for 2h;

4,4'-diamino-[1,1'-bianthracene]-9,9',10,10'-tetraone (4051-63-2) + 2-(benzyloxy)ethyl chloroformate (56456-19-0) → C48H36N2O10 (1228443-13-7)

Conditions	Yield
In dichlorobenzene, 1,2- at 185℃; for 10h;

4,4'-diamino-[1,1'-bianthracene]-9,9',10,10'-tetraone (4051-63-2) + chloroacetyl chloride (79-04-9) → C32H18Cl2N2O6 (1228443-10-4)

Conditions	Yield
In chlorobenzene at 100℃; for 4h;

3-cyclohexanecarbonyl chloride (462661-49-0) + 4,4'-diamino-[1,1'-bianthracene]-9,9',10,10'-tetraone (4051-63-2) → C42H36N2O6 (1228443-09-1)

Conditions	Yield
In dichlorobenzene, 1,2- at 180℃; for 1h;

1,3,5-trichloro-2,4,6-triazine (108-77-0) + 4,4'-diamino-[1,1'-bianthracene]-9,9',10,10'-tetraone (4051-63-2) + N-(3-aminopropyl)cyclohexylamine (3312-60-5) → C70H90N16O4

Conditions	Yield
Stage #1: 1,3,5-trichloro-2,4,6-triazine; 4,4'-diamino-[1,1'-bianthracene]-9,9',10,10'-tetraone With N,N-dimethyl acetamide at 100 - 110℃; for 5h; Stage #2: N-(3-aminopropyl)cyclohexylamine at 130 - 140℃; for 3h;

4,4'-diamino-[1,1'-bianthracene]-9,9',10,10'-tetraone (4051-63-2) + 4-hydroxy-3,5-di-tert-butylphenylpropionic acid (20170-32-5) → C62H64N2O8

Conditions	Yield
Stage #1: 4-hydroxy-3,5-di-tert-butylphenylpropionic acid With thionyl chloride In N,N-dimethyl acetamide at 40 - 50℃; for 0.5h; Stage #2: 4,4'-diamino-[1,1'-bianthracene]-9,9',10,10'-tetraone In N,N-dimethyl acetamide at 120 - 130℃; for 3h;

Upstream product

• 69166-06-9 4,4'-diamino-1,1'-dianthraquinonyl-3,3'-disulfonic acid 
• 6022-22-6 disodium 4,4'-diamino-1,1'-bianthraquinonyl-3,3'-disulfonate 
• 116-81-4 1-amino-4-bromo-9,10-dioxoanthracene-2-sulphonic acid 
• 81-45-8 1-benzamido-4-chloroanthraquinone 
• 94117-83-6 4,4'-Dibenzoylamino-1,1'-bianthraquinonyl 
• 6337-82-2 1-Nitro-4-chloroanthraquinone 

Downstream Products

• 94117-83-6 4,4'-Dibenzoylamino-1,1'-bianthraquinonyl 
• 1228443-09-1 C₄₂H₃₆N₂O₆ 
• 1228443-13-7 C₄₈H₃₆N₂O₁₀ 
• 1228443-12-6 C₅₂H₃₂N₂O₈S₂ 
• 1228443-08-0 C₄₆H₄₄N₂O₆ 

Relevant articles and documents

Method for efficiently preparing 4,4-diamino-1,1-dianthraquinone by using Bronsted acid functionalized ionic liquid

The invention discloses a method for efficiently preparing 4,4-diamino-1,1-dianthraquinone by using Bronsted acid functionalized ionic liquid. The method comprises the steps: weighing the Bronsted acid functionalized ionic liquid, adding the weighed Bronsted acid functionalized ionic liquid into a reaction vessel, and heating the temperature of the Bronsted acid functionalized ionic liquid to a certain temperature; slowly adding sodium 4,4-diamino-1,1-dianthraquinone-3,3-disulfonate, carrying out a heated reaction for certain time with stirring, and cooling the temperature of a reacted substance to a certain temperature after the reaction ends up; dropwise adding a certain amount of organic solvent, carrying out uniform stirring, then, carrying out suction filtration, and washing the reacted substance with the solvent until the reacted substance is colorless; and subjecting a filter cake to vacuum drying, thereby obtaining the 4,4-diamino-1,1-dianthraquinone. According to the method, concentrated sulfuric acid is replaced with the Bronsted acid functionalized ionic liquid which serves as a reaction medium for producing the 4,4-diamino-1,1-dianthraquinone, no waste acid is discharged, the yield of the 4,4-diamino-1,1-dianthraquinone reaches up to 98% or more, and thus, the method is in line with general orientation of environment-friendly and cyclic development and has a broad application prospect.

Pigmentation process for paratonere 3BL

The invention discloses a pigmentation process for paratonere 3BL. The process comprises the following steps: subjecting a crude 3BL product to dry ball milling in the presence of a grinding aid, an organic solvent and a dispersant for 4 to 5 h; after completion of ball milling, pouring a material obtained after ball milling into an aqueous medium containing a nonionic surfactant; maintaining a temperature of 70 to 80 DEG C for 1 to 2 h; and carrying out filtering washing and drying so as to obtain a finished 3BL product; wherein the addition amount of the grinding aid is 3 to 7 times the weight of the crude 3BL product, the addition amount of the organic solvent is 5 to 10% of the weight of the crude 3BL product, and the addition amount of the dispersant is 1 to 3% of the weight of the crude 3BL product. The pigmentation process for paratonere 3BL is simple in process steps and mild in reaction conditions, and uses easily available raw materials; and the prepared finished 3BL product has high strength, good dispersity, good glossiness and good stability. The finished 3BL product is applicable to blending of a variety of industrial paints and has brilliant colored light and good fluidity.

SOME RELATIONSHIPS IN THE SYNTHESIS OF BIARYLS FROM HALOGENOANTHRAQUINONES

The effects of the solvent and the concentration of the reagents on the reaction path and on the results of the synthesis of biaryls from halogenoanthraquinones were investigated for the case of the reaction of 1-chloro-4-benzoylaminoanthraquinone with copper.The use of concentrated reaction mixtures and of donating aprotic dipolar solvents with copper-aryl halide ratios slightly exceeding an equimolar ratio leads to a reduction in the induction period and to an increase in the yield of the biaryls.This explained by interaction between the copmonents of the metal-aryl halide-solvent complex.