3089-17-6

Basic information

• Product Name: Pigment Red 202
• Synonyms: Magenta RV-6830;2,3-Dichloroquinacridone;2,9-Dichloro-5,12-diazapentacene-7,14(5H,12H)-dione;2,9-Dichloroquino[2,3-b]acridine-7,14(5H,12H)-dione;2,9-dichloro-5,12-dihydroquinolino[2,3-b]acridine-7,14-dione;2,9-dichloro-5,12-dihydroquinolino[2,3-b]acridine-7,14-quinone;2,9-Dichloro[2,3-b]acridine-7,14(5H,12H)-dione;2,9-Dichloro[2,3-b]acridine-7,14(5H,12H)-dione
• CAS NO: 3089-17-6
• Molecular Formula: C₂₀H₁₀Cl₂N₂O₂
• Molecular Weight: 381.2116
• EINECS: 221-424-4
• Product Categories: Organics
• Mol File: 3089-17-6.mol

Chemical Properties

• Boiling Point: 629.4 °C at 760 mmHg
• Flash Point: 334.5 °C
• Appearance: /
• Density: 1.514 g/cm³
• Vapor Pressure: 9.37E-16mmHg at 25°C
• Refractive Index: 1.707
• PKA: -4.01±0.20(Predicted)
• CAS DataBase Reference: Pigment Red 202(CAS DataBase Reference)
• NIST Chemistry Reference: Pigment Red 202(3089-17-6)
• EPA Substance Registry System: Pigment Red 202(3089-17-6)

Safety Data

• Hazardous Substances Data: 3089-17-6(Hazardous Substances Data)

Usage

Uses

Pigment Red 202 is used in preparation method of colored modified nylon particles.

Properties and Applications

TEST ITEMS SPECIFICATION APPEARANCE RED POWDER SHADE BLUISH HEAT RESISTANCE 300 °C min LIGHT FASTNESS 7-8 ACID RESISTANCE 5 ALKALI RESISTANCE 5 FASTNESS TO BLEEDING 5 OIL ABSORPTION 40-45% SPECIFIC SURFACE 28 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

HEAT RESISTANCE

300 °C min

LIGHT FASTNESS

7-8

ACID RESISTANCE

5

ALKALI RESISTANCE

5

FASTNESS TO BLEEDING

5

OIL ABSORPTION

40-45%

SPECIFIC SURFACE

28 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/C20H10Cl2N2O2/c21-9-1-3-15-11(5-9)19(25)13-8-18-14(7-17(13)23-15)20(26)12-6-10(22)2-4-16(12)24-18/h1-8H,(H,23,25)(H,24,26)

Synthetic route

2,5-di(4-chloro-anilino)terephthalic acid (41680-76-6) → 2,9-dichloroquinacridone (3089-17-6)

Conditions	Yield
With polyphosphoric acid PPA at 125℃; for 6h; Dieckmann Condensation; Reflux;	99.53%

2,9-dichloroquinacridone (3089-17-6) + dimethyl 5-chloromethyl-1,3-benzenedicarboxylate (252210-01-8) → QAD-3 (937371-89-6)

Conditions	Yield
Stage #1: 2,9-dichloroquinacridone With potassium tert-butylate In dimethyl sulfoxide at 110℃; for 1h; Stage #2: dimethyl 5-chloromethyl-1,3-benzenedicarboxylate In dimethyl sulfoxide at 40℃; for 4h;	100%

2,9-dichloroquinacridone (3089-17-6) + malononitrile (109-77-3) → 2,2'-(2,9-dichloro-5,12-dioctylquinolino[2,3-b]acridine-7,14(5H,12H)-diylidene)dimalononitrile

Conditions	Yield
Stage #1: 2,9-dichloroquinacridone With N,N-dimethyl-formamide; trichlorophosphate In 1,2-dichloro-ethane at 60℃; for 2h; Stage #2: malononitrile With 2,4,6-trimethyl-pyridine In 1,2-dichloro-ethane at 20℃; for 48h;	58%

4-heptylpyrocarbonate + 2,9-dichloroquinacridone (3089-17-6) → C36H38Cl2N2O6

C22H34O5 + 2,9-dichloroquinacridone (3089-17-6) → C42H42Cl2N2O6

C22H38O5 + 2,9-dichloroquinacridone (3089-17-6) → C42H46Cl2N2O6

C20H22O5 + 2,9-dichloroquinacridone (3089-17-6) → C40H30Cl2N2O6

formaldehyd (50-00-0) + sodium 1-naphthalenesulfonate (130-14-3) + 2-naphthalenesulfonic acid sodium salt (532-02-5) + 2,9-dichloroquinacridone (3089-17-6) → poly(formaldehyde-co-1-naphtalene sulfonic acid sodium salt-co-2-naphtalene sulfonic acid sodium salt); 2,9-dichloroquinacridone; mixture of

Conditions	Yield
Stage #1: 2,9-dichloroquinacridone With sulfuric acid at 48 - 52℃; for 0.333333h; Stage #2: sodium 1-naphthalenesulfonate; 2-naphthalenesulfonic acid sodium salt In water at 40 - 45℃; for 0.5h; Stage #3: formaldehyd In water at 58 - 60℃; for 1h;

1-bromo-hexane (111-25-1) + 2,9-dichloroquinacridone (3089-17-6) → C30H16Cl2N4O2

Conditions	Yield
With tri-tert-butyl phosphine; potassium tert-butylate; palladium diacetate at 86℃; for 7h; Concentration; Temperature; Inert atmosphere;

3-bromo-9-phenyl-9H-carbazole (1153-85-1) + 2,9-dichloroquinacridone (3089-17-6) → C56H32Cl2N4O2

Conditions	Yield
With tri-tert-butyl phosphine; potassium tert-butylate; palladium diacetate at 86℃; for 7h; Concentration; Temperature; Inert atmosphere;

2,9-dichloroquinacridone (3089-17-6) → C44H28N2O2

Conditions	Yield
Multi-step reaction with 2 steps 1: tri-tert-butyl phosphine; potassium tert-butylate; palladium diacetate / 7 h / 85 °C / Inert atmosphere 2: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / toluene; water / 24 h / Reflux; Inert atmosphere View Scheme

2,9-dichloroquinacridone (3089-17-6) → C56H40N2O2

Conditions	Yield
Multi-step reaction with 3 steps 1.1: tri-tert-butyl phosphine; potassium tert-butylate; palladium diacetate / 7 h / 85 °C / Inert atmosphere 2.1: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / toluene; water / 24 h / Reflux; Inert atmosphere 3.1: n-butyllithium / tetrahydrofuran / 2 h / -78 °C / Inert atmosphere 3.2: 9 h / -78 - 20 °C / Inert atmosphere View Scheme

2,9-dichloroquinacridone (3089-17-6) → C56H40N2

Conditions

Yield

Multi-step reaction with 4 steps 1.1: tri-tert-butyl phosphine; potassium tert-butylate; palladium diacetate / 7 h / 85 °C / Inert atmosphere 2.1: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / toluene; water / 24 h / Reflux; Inert atmosphere 3.1: n-butyllithium / tetrahydrofuran / 2 h / -78 °C / Inert atmosphere 3.2: 9 h / -78 - 20 °C / Inert atmosphere 4.1: sulfuric acid / 9 h / 20 °C View Scheme

bromobenzene (108-86-1) + 2,9-dichloroquinacridone (3089-17-6) → 2,9-dichloro-5,12-diphenyl-5,12-dihydro-quino[2,3-b]acridine-7,14-dione

Conditions	Yield
With tri-tert-butyl phosphine; potassium tert-butylate; palladium diacetate at 85℃; for 7h; Inert atmosphere;

1-bromo-octane (111-83-1) + 2,9-dichloroquinacridone (3089-17-6) → 2,9-dichloro-5,12-dioctylquinolino[2,3-b]acridine-7,14(5H,12H)-dione

Conditions	Yield
With N,N,N,N,N,N-hexamethylphosphoric triamide; tetrabutylammomium bromide; sodium hydride In mineral oil; benzene at 20 - 50℃; for 105h;	0.32 g

Upstream product

• 41680-76-6 2,5-di(4-chloro-anilino)terephthalic acid 

Downstream Products

• 937371-89-6 QAD-3 

Relevant articles and documents

Preparation method for quinacridone and derivatives of quinacridone

The invention relates to the field of synthesis of organic pigments and discloses a preparation method for quinacridone and derivatives of the quinacridone. The preparation method comprises the steps that dimethyl succinate generates sodium dimethyl succinylsuccinate (DMSS) through cyclic condensation under an effect of sodium methoxide, and then being acidized into DMSS; condensation reaction occurs between the DMSS and aniline or substituted aniline, an intermediate product generated during condensation is directly oxidized and dehydrogenated by sodium 3-nitrobenzene sulfonate to obtain an oxidative product; and finally coarse products of the quinacridone or the derivatives of the quinacridone are prepared from the oxidative product in a ring-closing mode under an effect of polyphosphoric acid, and finally finished products of the quinacridone or the derivatives of the quinacridone are obtained through pigmentation treatment.

Quinacridone pigment compositions comprising unsymmetrically substituted components

The present invention relates to a novel quinacridone pigment compositions, a process using a mixed amine synthesis for the ultimate production of the compositions and to their use as colorants for pigmenting high molecular weight organic materials.