980-26-7

Basic information

• Product Name: Pigment Red 122
• Synonyms: TRANSQUINACRIDONE;acramin scarlet ldcn;Pigment red 122 (C.I. 73915);[2,3-b]Acridine-7,14-dione, 5,12-dihydro-2,9-dimethyl-quino;5,12-Dihydro-2,9-dimethylquino[2,3-b]acridine-7,14-dione;C.I. 73915;Pigment Red 122;Quindo Red -W
• CAS NO: 980-26-7
• Molecular Formula: C₂₂H₁₆N₂O₂
• Molecular Weight: 340.37
• EINECS: 213-561-3
• Mol File: 980-26-7.mol
• Article Data: 9

Chemical Properties

• Melting Point: 440℃
• Boiling Point: 601.6 °C at 760 mmHg
• Flash Point: 221.4 °C
• Appearance: chip
• Density: 1.307 g/cm³
• Vapor Pressure: 1.98E-14mmHg at 25°C
• Refractive Index: 1.676
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: -2.49±0.20(Predicted)
• CAS DataBase Reference: Pigment Red 122(CAS DataBase Reference)
• NIST Chemistry Reference: Pigment Red 122(980-26-7)
• EPA Substance Registry System: Pigment Red 122(980-26-7)

Safety Data

• Hazardous Substances Data: 980-26-7(Hazardous Substances Data)

Usage

General Description

Pigment Red 122 is a red organic pigment that is commonly used in a variety of applications, including paints, inks, plastics, and textiles. It is known for its vibrant, high-strength red color, as well as its excellent lightfastness and weather resistance. The chemical composition of Pigment Red 122 consists of a metal salt complex of 1,4-diketopyrrolo[3,4-c]pyrrole and benzimidazolone. This complex structure gives the pigment its intense color and makes it suitable for use in a wide range of industrial and consumer products. Additionally, Pigment Red 122 has low toxicity and is considered safe for use in a variety of applications.

InChI:InChI=1/C22H16N2O2/c1-11-3-5-17-13(7-11)21(25)15-9-20-16(10-19(15)23-17)22(26)14-8-12(2)4-6-18(14)24-20/h3-10H,1-2H3,(H,23,25)(H,24,26)

Synthetic route

2,5-di(4'-methylphenylamino)terephthalic acid (10291-28-8) → C.I. Pigment Red 122 (980-26-7)

Conditions	Yield
With polyphosphoric acid PPA at 125℃; for 6h; Dieckmann Condensation;	99.59%
With phosphoric acid; phosphorus pentoxide at 20 - 130℃; for 2.25h; Product distribution / selectivity;	97%
With PPA at 20 - 130℃; for 2.25h; Product distribution / selectivity;	85%

2,9-dimethyl-6,13-dihydroquinacridone (13796-22-0) → C.I. Pigment Red 122 (980-26-7)

Conditions	Yield
With dihydrogen peroxide; potassium hydroxide at 90 - 110℃; for 4h; pH=10 - 11; pH-value; Temperature;	91.13%
With sodium hydroxide; dihydrogen peroxide In water; polyethylene glycol 400 at 20 - 60℃; for 1h; Product distribution / selectivity;

C21H18N2O4 (67906-32-5) + 2,5-di(phenylamino)-terephthalic acid (10109-95-2) + 2,5-di(4'-methylphenylamino)terephthalic acid (10291-28-8) → Quinacridone (1047-16-1) + C.I. Pigment Red 122 (980-26-7) + 5,12-dihydro-2-methylquino[2,3-b]acridine-7,14-dione (10228-01-0)

Conditions	Yield
With PPA at 90 - 125℃; for 3h;
With PPA at 90 - 125℃; for 3h;
With PPA at 90 - 125℃; for 3h;
With PPA at 90 - 125℃; for 3h;

dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate (6289-46-9) + p-toluidine (106-49-0) → C.I. Pigment Red 122 (980-26-7)

Conditions	Yield
Stage #1: dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate; p-toluidine With phosphoric acid at 20 - 100℃; for 4h; Stage #2: With sodium hydroxide; sodium 3-nitrobenzenesulfonate In water for 4h; Heating / reflux; Stage #3: With sulfuric acid pH=3; Product distribution / selectivity;

2,5-di-p-toluidino-terephthalic acid dimethyl ester (114508-42-8) → C.I. Pigment Red 122 (980-26-7)

Conditions	Yield
With toluene-4-sulfonic acid for 0.166667h; Product distribution / selectivity; Heating / reflux;
Multi-step reaction with 2 steps 1: sodium hydroxide / 3 h / 110 °C / Reflux 2: polyphosphoric acid PPA / 6 h / 125 °C View Scheme

2,5-di(4'-methylphenylamino)terephthalic acid (10291-28-8) + C22H17N3O3 → C.I. Pigment Red 122 (980-26-7) + C21H13N3O2

Conditions	Yield
With polyphosphoric acid at 120 - 130℃; for 2h;

C.I. Pigment Red 122 (980-26-7) + 4-Chlorobutanoyl chloride (4635-59-0) → 2,9-dimethyl-3,10-di(4-chlorobutyryl)quinacridone

Conditions	Yield
With zirconium chloride In tetrachloromethane at 10 - 60℃; for 48h;	90%

1 ,6-dibromohexane (629-03-8) + C.I. Pigment Red 122 (980-26-7) → 2,9-dimethyl-5,12-bis(6-bromohexyl)-5,12-dihydroquino[2,3-b]acridine-7,14-dione

Conditions	Yield
With sodium hydride In tetrahydrofuran for 24h; Reflux;	65%

Acetyl bromide (506-96-7) + C.I. Pigment Red 122 (980-26-7) → C24H18N2O3 (1415414-23-1)

Conditions	Yield
With sodium hydride In 1-methyl-pyrrolidin-2-one	38%

propanoyl bromide (598-22-1) + C.I. Pigment Red 122 (980-26-7) → C25H20N2O3 (1415414-24-2)

Conditions	Yield
With sodium hydride In 1-methyl-pyrrolidin-2-one	36%

C.I. Pigment Red 122 (980-26-7) + bromoacetic acid methyl ester (96-32-2) → C25H20N2O4 (1415414-25-3)

Conditions	Yield
With sodium hydride In 1-methyl-pyrrolidin-2-one	28%

C.I. Pigment Red 122 (980-26-7) + ethyl bromoacetate (105-36-2) → C26H22N2O4 (1415414-26-4)

Conditions	Yield
With sodium hydride In 1-methyl-pyrrolidin-2-one	25%

1-bromo dodecane (112-29-8) + C.I. Pigment Red 122 (980-26-7) → C32H36N2O2 (1415414-22-0)

Conditions	Yield
With sodium hydride In 1-methyl-pyrrolidin-2-one	23%

1-bromo-octane (111-83-1) + C.I. Pigment Red 122 (980-26-7) → 2,9-dimethyl-5-octylquinolino[2,3-b]acridine-7,14(5H,12H)-dione (1415414-21-9)

Conditions	Yield
Stage #1: C.I. Pigment Red 122 With sodium hydride In 1-methyl-pyrrolidin-2-one at 20℃; for 2h; Stage #2: 1-bromo-octane In 1-methyl-pyrrolidin-2-one at 70℃; for 20h;	21%

C.I. Pigment Red 122 (980-26-7) → appr. radical-cations and -anions

Conditions	Yield
In dichloromethane electrochemical reduction i.e. oxidation, tetrabutylammonium perchlorate as electrolyte, platinum electrode, products investigated by ESR-methods;
In various solvent(s) at 25℃; Irradiation; reaction products investigated by ESR-methods;

2,5-di(4'-methylphenylamino)terephthalic acid (10291-28-8) → C.I. Pigment Red 122 (980-26-7)

Conditions	Yield
With polyphosphoric acid PPA at 125℃; for 6h; Dieckmann Condensation;	99.59%
With phosphoric acid; phosphorus pentoxide at 20 - 130℃; for 2.25h; Product distribution / selectivity;	97%
With PPA at 20 - 130℃; for 2.25h; Product distribution / selectivity;	85%

2,9-dimethyl-6,13-dihydroquinacridone (13796-22-0) → C.I. Pigment Red 122 (980-26-7)

Conditions	Yield
With dihydrogen peroxide; potassium hydroxide at 90 - 110℃; for 4h; pH=10 - 11; pH-value; Temperature;	91.13%
With sodium hydroxide; dihydrogen peroxide In water; polyethylene glycol 400 at 20 - 60℃; for 1h; Product distribution / selectivity;

C21H18N2O4 (67906-32-5) + 2,5-di(phenylamino)-terephthalic acid (10109-95-2) + 2,5-di(4'-methylphenylamino)terephthalic acid (10291-28-8) → Quinacridone (1047-16-1) + C.I. Pigment Red 122 (980-26-7) + 5,12-dihydro-2-methylquino[2,3-b]acridine-7,14-dione (10228-01-0)

Conditions	Yield
With PPA at 90 - 125℃; for 3h;
With PPA at 90 - 125℃; for 3h;
With PPA at 90 - 125℃; for 3h;
With PPA at 90 - 125℃; for 3h;

dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate (6289-46-9) + p-toluidine (106-49-0) → C.I. Pigment Red 122 (980-26-7)

Conditions	Yield
Stage #1: dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate; p-toluidine With phosphoric acid at 20 - 100℃; for 4h; Stage #2: With sodium hydroxide; sodium 3-nitrobenzenesulfonate In water for 4h; Heating / reflux; Stage #3: With sulfuric acid pH=3; Product distribution / selectivity;

2,5-di-p-toluidino-terephthalic acid dimethyl ester (114508-42-8) → C.I. Pigment Red 122 (980-26-7)

Conditions	Yield
With toluene-4-sulfonic acid for 0.166667h; Product distribution / selectivity; Heating / reflux;
Multi-step reaction with 2 steps 1: sodium hydroxide / 3 h / 110 °C / Reflux 2: polyphosphoric acid PPA / 6 h / 125 °C View Scheme

2,5-di(4'-methylphenylamino)terephthalic acid (10291-28-8) + C22H17N3O3 → C.I. Pigment Red 122 (980-26-7) + C21H13N3O2

Conditions	Yield
With polyphosphoric acid at 120 - 130℃; for 2h;

C.I. Pigment Red 122 (980-26-7) + 4-Chlorobutanoyl chloride (4635-59-0) → 2,9-dimethyl-3,10-di(4-chlorobutyryl)quinacridone

Conditions	Yield
With zirconium chloride In tetrachloromethane at 10 - 60℃; for 48h;	90%

1 ,6-dibromohexane (629-03-8) + C.I. Pigment Red 122 (980-26-7) → 2,9-dimethyl-5,12-bis(6-bromohexyl)-5,12-dihydroquino[2,3-b]acridine-7,14-dione

Conditions	Yield
With sodium hydride In tetrahydrofuran for 24h; Reflux;	65%

Acetyl bromide (506-96-7) + C.I. Pigment Red 122 (980-26-7) → C24H18N2O3 (1415414-23-1)

Conditions	Yield
With sodium hydride In 1-methyl-pyrrolidin-2-one	38%

propanoyl bromide (598-22-1) + C.I. Pigment Red 122 (980-26-7) → C25H20N2O3 (1415414-24-2)

Conditions	Yield
With sodium hydride In 1-methyl-pyrrolidin-2-one	36%

C.I. Pigment Red 122 (980-26-7) + bromoacetic acid methyl ester (96-32-2) → C25H20N2O4 (1415414-25-3)

Conditions	Yield
With sodium hydride In 1-methyl-pyrrolidin-2-one	28%

C.I. Pigment Red 122 (980-26-7) + ethyl bromoacetate (105-36-2) → C26H22N2O4 (1415414-26-4)

Conditions	Yield
With sodium hydride In 1-methyl-pyrrolidin-2-one	25%

1-bromo dodecane (112-29-8) + C.I. Pigment Red 122 (980-26-7) → C32H36N2O2 (1415414-22-0)

Conditions	Yield
With sodium hydride In 1-methyl-pyrrolidin-2-one	23%

1-bromo-octane (111-83-1) + C.I. Pigment Red 122 (980-26-7) → 2,9-dimethyl-5-octylquinolino[2,3-b]acridine-7,14(5H,12H)-dione (1415414-21-9)

Conditions	Yield
Stage #1: C.I. Pigment Red 122 With sodium hydride In 1-methyl-pyrrolidin-2-one at 20℃; for 2h; Stage #2: 1-bromo-octane In 1-methyl-pyrrolidin-2-one at 70℃; for 20h;	21%

C.I. Pigment Red 122 (980-26-7) → appr. radical-cations and -anions

Conditions	Yield
In dichloromethane electrochemical reduction i.e. oxidation, tetrabutylammonium perchlorate as electrolyte, platinum electrode, products investigated by ESR-methods;
In various solvent(s) at 25℃; Irradiation; reaction products investigated by ESR-methods;

C.I. Pigment Red 122 (980-26-7) → C22H14N2O2(2-)*2Na(1+)

Conditions	Yield
With sodium t-butanolate In tert-butyl alcohol at 30 - 90℃; under 37.5038 - 600.06 Torr;

formaldehyd (50-00-0) + C.I. Pigment Red 122 (980-26-7) + sodium 1-naphthalenesulfonate (130-14-3) + 2-naphthalenesulfonic acid sodium salt (532-02-5) → poly(formaldehyde-co-1-naphtalene sulfonic acid sodium salt-co-2-naphtalene sulfonic acid sodium salt); 2,9-dimethylquinacridone; mixture of

Conditions	Yield
Stage #1: C.I. Pigment Red 122 With sulfuric acid at 40 - 45℃; for 0.166667h; 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;

polyoxyethylene lauryl ether + [1,3]-dioxolan-2-one (96-49-1) + methanesulfonic acid (75-75-2) + polyoxycetyl ether + C.I. Pigment Red 122 (980-26-7) → Reaxys ID: 20190102

Conditions	Yield
Stage #1: methanesulfonic acid; C.I. Pigment Red 122 at 120℃; for 0.333333h; Stage #2: polyoxyethylene lauryl ether; [1,3]-dioxolan-2-one; polyoxycetyl ether In water; acetonitrile at 20℃;

trimethylene carbonate (2453-03-4) + methanesulfonic acid (75-75-2) + polyoxycetyl ether + C.I. Pigment Red 122 (980-26-7) + acetic acid (64-19-7) → Reaxys ID: 20190098

Conditions	Yield
Stage #1: methanesulfonic acid; C.I. Pigment Red 122 at 150℃; for 0.333333h; Stage #2: trimethylene carbonate; polyoxycetyl ether; acetic acid In methanol; water at 20℃;

C.I. Pigment Red 122 (980-26-7) → C46H66N6O4(2+)*2Cl(1-)

Conditions	Yield
Multi-step reaction with 2 steps 1: zirconium chloride / tetrachloromethane / 48 h / 10 - 60 °C 2: acetonitrile / 8 h / Reflux View Scheme

C.I. Pigment Red 122 (980-26-7) → C48H72N6O4(4+)*2O4S(2-)

Conditions	Yield
Multi-step reaction with 3 steps 1: zirconium chloride / tetrachloromethane / 48 h / 10 - 60 °C 2: acetonitrile / 8 h / Reflux 3: acetonitrile / 4 h / Reflux View Scheme

C.I. Pigment Red 122 (980-26-7) + C55H104N2O23 → C132H218N4O48 + C77H117N3O25

Conditions	Yield
Stage #1: C55H104N2O23 With hydrogenchloride; sodium nitrite In water for 0.333333h; Stage #2: C.I. Pigment Red 122 In water at 50℃; pH=5 - 6;

C.I. Pigment Red 122 (980-26-7) + C102H198N2O43 → C124H211N3O45

Conditions	Yield
Stage #1: C102H198N2O43 With hydrogenchloride; sodium nitrite In water for 0.333333h; Stage #2: C.I. Pigment Red 122 In water at 50℃; pH=5 - 6;

C.I. Pigment Red 122 (980-26-7) + C148H290N2O67 → C170H303N3O69

Conditions	Yield
Stage #1: C148H290N2O67 With hydrogenchloride; sodium nitrite In water for 0.333333h; Stage #2: C.I. Pigment Red 122 In water at 50℃; pH=5 - 6;

1-bromo-octane (111-83-1) + C.I. Pigment Red 122 (980-26-7) → 2,9-dimethyl-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;	0.44 g

C.I. Pigment Red 122 (980-26-7) → 2-(2,9-dimethyl-5,12-dioctyl-14-oxoquinolino[2,3-b]acridin-7(5H,12H,14H)-ylidene)malononitrile

Conditions	Yield
Multi-step reaction with 3 steps 1: N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydride; tetrabutylammomium bromide / benzene; mineral oil / 105 h / 20 - 50 °C 2: trichlorophosphate; N,N-dimethyl-formamide / 1,2-dichloro-ethane / 2 h / 60 °C 3: 2,4,6-trimethyl-pyridine / 2 h / 20 °C View Scheme

Upstream product

• 10291-28-8 2,5-di(4'-methylphenylamino)terephthalic acid 
• 114508-42-8 2,5-di-p-toluidino-terephthalic acid dimethyl ester 
• 6289-46-9 dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate 
• 106-49-0 p-toluidine 
• 13796-22-0 2,9-dimethyl-6,13-dihydroquinacridone 
• 67906-32-5 C₂₁H₁₈N₂O₄ 
• 10109-95-2 2,5-di(phenylamino)-terephthalic acid 

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