129-39-5

Basic information

• Product Name: 1,8-DINITROANTHRAQUINONE
• Synonyms: 1,8-dinitro-10-anthracenedione;1,8-Dinitro-9,10-anthracenedione;10-Anthracenedione,1,8-dinitro-9;1,8-DINITROANTHRAQUINONE;1,8-dinitroanthracene-9,10-dione;1,8-DINITRO ANTHRAQUINONE 97% MIN;1,8-Dinitro-9,10-anthraquinone;1,8-Dinitroanthraquinone 97%
• CAS NO: 129-39-5
• Molecular Formula: C₁₄H₆N₂O₆
• Molecular Weight: 298.21
• EINECS: 204-943-0
• Product Categories: Intermediates of Dyes and Pigments;C13 to C14;Carbonyl Compounds;Ketones
• Mol File: 129-39-5.mol
• Article Data: 7

Chemical Properties

• Melting Point: 318-322 °C(lit.)
• Boiling Point: 563.4 ºC at 760 mmHg
• Flash Point: 294 ºC
• Appearance: /
• Density: 1.631 g/cm³
• Vapor Pressure: 1.02E-12mmHg at 25°C
• Refractive Index: 1.714
• Storage Temp.: -20°C, Inert atmosphere
• Solubility: DMSO (Slightly, Heated, Sonicated), Methanol (Slightly)
• CAS DataBase Reference: 1,8-DINITROANTHRAQUINONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,8-DINITROANTHRAQUINONE(129-39-5)
• EPA Substance Registry System: 1,8-DINITROANTHRAQUINONE(129-39-5)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 129-39-5(Hazardous Substances Data)

Usage

Uses

1,8-Dinitroanthracene-9,10-dione is used in preparation method of disperse dyes using 1-aminoanthraquinone DMF residue.

InChI:InChI=1/C14H6N2O6/c17-13-7-3-1-5-9(15(19)20)11(7)14(18)12-8(13)4-2-6-10(12)16(21)22/h1-6H

Synthetic route

1.5-dinitroanthraquinone (82-35-9) → 1,8-dinitroanthraquinone (129-39-5)

Conditions	Yield
In 5,5-dimethyl-1,3-cyclohexadiene	77%

1-amino-8-nitro-anthraquinone (59471-77-1) → 1,8-dinitroanthraquinone (129-39-5)

Conditions	Yield
With peracetic acid

3-nitro-2-(2-nitro-benzoyl)-benzoic acid → 1,8-dinitroanthraquinone (129-39-5)

Conditions	Yield
With sulfuric acid; boric acid at 150℃;

9,10-phenanthrenequinone (84-65-1) → 1-nitroanthraquinone (82-34-8) + 1.5-dinitroanthraquinone (82-35-9) + 1,8-dinitroanthraquinone (129-39-5)

Conditions	Yield
With phosphoric acid; sulfuric acid; nitric acid In tetrachloromethane at 55℃; for 0.5h; var. mole ratio of acids, var. temp. and time;

9,10-phenanthrenequinone (84-65-1) → 1.5-dinitroanthraquinone (82-35-9) + 1,8-dinitroanthraquinone (129-39-5)

Conditions	Yield
With sulfuric acid; nitric acid multistep reaction; potentiometric studies of optimum reaction conditions;
With sulfuric acid; nitric acid Yield given. Yields of byproduct given;
With sulfuric acid; nitric acid 20 to 25 deg C; 3 h; Yield given. Yields of byproduct given;

9,10-phenanthrenequinone (84-65-1) + HNO3+H2SO4 → 1.5-dinitroanthraquinone (82-35-9) + 1,7-dinitro-anthraquinone (1604-43-9) + 1,8-dinitroanthraquinone (129-39-5) + 2,6-dinitro-anthraquinone (1604-40-6)

Conditions	Yield
Product distribution;

sulfuric acid (7664-93-9) + nitric acid (7697-37-2) + 9,10-phenanthrenequinone (84-65-1) → 1.5-dinitroanthraquinone (82-35-9) + 1,7-dinitro-anthraquinone (1604-43-9) + 1,8-dinitroanthraquinone (129-39-5) + 1,6-dinitro-anthraquinone (1604-42-8)

Conditions	Yield
at 80℃;

9,10-phenanthrenequinone (84-65-1) + HNO3+H2SO4 → 1.5-dinitroanthraquinone (82-35-9) + 1,7-dinitro-anthraquinone (1604-43-9) + 1,8-dinitroanthraquinone (129-39-5) + 1,6-dinitro-anthraquinone (1604-42-8)

Conditions	Yield
Product distribution;

9,10-phenanthrenequinone (84-65-1) + HNO3+H2SO4 → 1,7-dinitro-anthraquinone (1604-43-9) + 1,8-dinitroanthraquinone (129-39-5) + 2,6-dinitro-anthraquinone (1604-40-6) + 1,6-dinitro-anthraquinone (1604-42-8)

1-nitroanthraquinone (82-34-8) + sulfuric acid (7664-93-9) + nitric acid (7697-37-2) → 1.5-dinitroanthraquinone (82-35-9) + 1,7-dinitro-anthraquinone (1604-43-9) + 1,8-dinitroanthraquinone (129-39-5) + 1,6-dinitro-anthraquinone (1604-42-8)

Conditions	Yield
at 80℃;

9,10-phenanthrenequinone (84-65-1) → 1,8-dinitroanthraquinone (129-39-5) + 1.5-, 1.6-, 1.7-, 2.6-and 2.7-dinitro-anthraquinone

Conditions	Yield
With sulfuric acid; nitric acid

1-nitroanthraquinone (82-34-8) → 1,8-dinitroanthraquinone (129-39-5) + 1.5-dinitro-anthraquinone, 1.6-dinitro-anthraquinone, 1.7-dinitro-anthraquinone

Conditions	Yield
With sulfuric acid; nitric acid at 80℃;

sulfuric acid (7664-93-9) + 3-nitro-2-(2-nitro-benzoyl)-benzoic acid + metaboric acid (13460-50-9) → 1,8-dinitroanthraquinone (129-39-5)

Conditions	Yield
at 150℃;

2-Benzylbenzoic acid (612-35-1) → 1,8-dinitroanthraquinone (129-39-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: nitric acid 2: chromic acid; acetic acid 3: fuming sulfuric acid; boric acid / 150 °C View Scheme

3-nitro-2-(2-nitro-benzyl)-benzoic acid → 1,8-dinitroanthraquinone (129-39-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: chromic acid; acetic acid 2: fuming sulfuric acid; boric acid / 150 °C View Scheme

9,10-phenanthrenequinone (84-65-1) → 1,8-dinitroanthraquinone (129-39-5)

dinitro-anthraquinone (57875-61-3) → 1,8-dinitroanthraquinone (129-39-5)

Conditions	Yield
In water; nitric acid

1,8-dinitroanthraquinone (129-39-5) → 1,8-diamino-anthraquinone (129-42-0)

Conditions	Yield
With sodium sulfide In ethanol; water for 12h; Heating;	98%
With sodium sulfide In ethanol; water for 64.5h; Reflux;	98%
With sodium sulfide; sodium hydroxide In ethanol; water for 6h; Reflux;	98%

α,α-dinitroanthraquinone + 1,8-dinitroanthraquinone (129-39-5) → HNO3 -moist 1,5-dinitroanthraquinone + 1.5-dinitroanthraquinone (82-35-9)

Conditions	Yield
	A n/a B 97.1%

N-Methylformamide (123-39-7) + 1,8-dinitroanthraquinone (129-39-5) → 1,8-bis-methylaminoanthraquinone (60316-43-0)

Conditions	Yield
In methanol	94.3%

1,8-dinitroanthraquinone (129-39-5) → anthracene-1,8-diamine (139312-39-3)

Conditions	Yield
With sodium tetrahydroborate In isopropyl alcohol for 36h; Inert atmosphere; Reflux;	93%
With sodium tetrahydroborate In isopropyl alcohol	30%
Multi-step reaction with 2 steps 1: 98 percent / Na2S*9H2O / H2O; ethanol / 12 h / Heating 2: 83 percent / NaBH4; NaOH / propan-2-ol / 8 h / Heating View Scheme

sulfonamide + 1,8-dinitroanthraquinone (129-39-5) → 1,8-dimethoxy-9,10-anthracenedione (6407-55-2)

Conditions	Yield
With potassium hydroxide In methanol	90%

1,8-dinitroanthraquinone (129-39-5) + chlorobenzene (108-90-7) → 1,8-bis(phenylthio)anthracene-9,10-dione (13676-91-0)

Conditions	Yield
Stage #1: chlorobenzene With potassium hydrosulfide; 18-crown-6 ether In dimethyl sulfoxide at 110 - 120℃; for 16h; Large scale; Stage #2: 1,8-dinitroanthraquinone In dimethyl sulfoxide at 40 - 50℃; Solvent; Reagent/catalyst; Large scale;	87.3%

1,8-dinitroanthraquinone (129-39-5) + N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine (93102-05-7) → 15,22-dinitro-6,7,13,14-dibenzo-3,11-dibenzyl-1,9-dioxa-3,11-diazadispiro[4.2.4.2]tetradecane

Conditions	Yield
With trifluoroacetic acid In dichloromethane at 0 - 20℃; for 5h; Inert atmosphere;	66%

1,8-dinitroanthraquinone (129-39-5) → 9,10-dihydro-1,8-diaminoanthracene (114645-02-2)

Conditions	Yield
With sodium tetrahydroborate In isopropyl alcohol for 43h; Inert atmosphere; Reflux;	31%
Multi-step reaction with 2 steps 1: sodium sulfide / ethanol; water / 64.5 h / Reflux 2: sodium hydroxide; sodium tetrahydroborate / isopropyl alcohol / 15.5 h / Inert atmosphere; Reflux View Scheme

piperidine (110-89-4) + 1,8-dinitroanthraquinone (129-39-5) → 1-nitro-8-piperidino-anthraquinone

Conditions	Yield
With pyridine at 60 - 70℃;

methanol (67-56-1) + 1,8-dinitroanthraquinone (129-39-5) → 1,8-dimethoxy-9,10-anthracenedione (6407-55-2)

Conditions	Yield
With sodium hydroxide
With sodium hydroxide

1,2,3,4-tetrahydroisoquinoline (635-46-1) + 1,8-dinitroanthraquinone (129-39-5) + acetic acid (64-19-7) → 1-amino-8-nitro-anthraquinone (59471-77-1)

4-ethoxy-benzenethiol (699-09-2) + 1,8-dinitroanthraquinone (129-39-5) → 1,8-bis-(4-ethoxy-phenylsulfanyl)-anthraquinone

Conditions	Yield
With alkali

1,8-dinitroanthraquinone (129-39-5) + potassium phenolate (100-67-4) → 1,8-diphenoxyanthracene-9,10-dione (82-17-7)

1,8-dinitroanthraquinone (129-39-5) → 1,8-dihydroxy-9,10-anthracenedione (117-10-2)

Conditions	Yield
With potassium acetate; acetic acid at 170℃;
Multi-step reaction with 2 steps 1: water; alkali sulfite 2: quicklime; water / 180 - 200 °C View Scheme
With pyridine
With quicklime; water at 190 - 200℃;

1,8-dinitroanthraquinone (129-39-5) → 1,8-anthraquinonedisulphonic acid (82-48-4)

Conditions	Yield
With alkali sulfite; water
With alkali sulfite; water

1,8-dinitroanthraquinone (129-39-5) → 1-amino-8-nitro-anthraquinone (59471-77-1)

Conditions	Yield
With 1,2,3,4-tetrahydroisoquinoline; acetic acid

1,8-dinitroanthraquinone (129-39-5) → 1,8-bis-hydroxyamino-anthraquinone (60080-33-3)

Conditions	Yield
With tin oxide; sodium carbonate

1,8-dinitroanthraquinone (129-39-5) → 1,8-diamino-2,4,5,7-tetrabromo-anthraquinone (3224-33-7)

Conditions	Yield
With bromine; acetic acid at 150℃; im geschlossenen Rohr;

1,8-dinitroanthraquinone (129-39-5) → 3,6-dihydroxy-4,5-diimino-1,8,9,10-tetraoxo-1,4,5,8,9,10-hexahydro-anthracene-2,7-disulfonic acid

Conditions	Yield
With sulfuric acid; sulfur trioxide; sulfur at 120 - 130℃; eventuell unter Zusatz von Borsaeure, bis zur Wasserloeslichkeit und Eingiessen der abgekuehlten Schmelze in eine auf -10grad gekuehlte 20prozentige NaCl- oder KCl-Loesung;

1,8-dinitroanthraquinone (129-39-5) + p-toluidine (106-49-0) → 1,8-bis(p-tolylamino)anthraquinone (82-16-6) + 1-nitro-8-p-toluidino-anthraquinone

Conditions	Yield
With pyridine

1,8-dinitroanthraquinone (129-39-5) + ethylamine (75-04-7) → 1-ethylamino-8-nitro-anthraquinone

Conditions	Yield
With pyridine at 50℃;

1,8-dinitroanthraquinone (129-39-5) + potassium acetate (127-08-2) + acetic acid (64-19-7) → 1,4-dihydroxy-9,10-anthracenedione (81-64-1)

Conditions	Yield
at 170℃;

1,8-dinitroanthraquinone (129-39-5) + ortho-cresol (95-48-7) → 1-nitro-8-o-tolyloxy-anthraquinone

Conditions	Yield
With potassium hydroxide

1,8-dinitroanthraquinone (129-39-5) + N,N-dimethyl-aniline (121-69-7) → 1-amino-8-nitro-anthraquinone (59471-77-1)

1,8-dinitroanthraquinone (129-39-5) + dimethyl amine (124-40-3) → 1-dimethylamino-8-nitro-anthraquinone

1,8-dinitroanthraquinone (129-39-5) + ethylenediamine (107-15-3) → 1,8-di(2-aminoethylamino)anthracene-9,10-dione (94068-88-9)

1,8-dinitroanthraquinone (129-39-5) + diethylamine (109-89-7) → 1-diethylamino-8-nitro-anthraquinone

Conditions	Yield
With pyridine at 50 - 70℃;

Upstream product

• 84-65-1 9,10-phenanthrenequinone 
• 82-35-9 1.5-dinitroanthraquinone 
• 57875-61-3 dinitro-anthraquinone 
• 612-35-1 2-Benzylbenzoic acid 
• 7664-93-9 sulfuric acid 
• 13460-50-9 metaboric acid 
• 82-34-8 1-nitroanthraquinone 
• 7697-37-2 nitric acid 
• 59471-77-1 1-amino-8-nitro-anthraquinone 

Downstream Products

• 129-42-0 1,8-diamino-anthraquinone 
• 82-35-9 1.5-dinitroanthraquinone 
• 129-38-4 8-chloro-1-nitroanthraquinone 
• 60316-43-0 1,8-bis-methylaminoanthraquinone 
• 6407-55-2 1,8-dimethoxy-9,10-anthracenedione 
• 13676-91-0 1,8-bis(phenylthio)anthracene-9,10-dione 
• 129-40-8 5-chloro-1-nitroanthraquinone 
• 53804-05-0 8-nitro-1-cyclohexylamino-anthraquinone 

Relevant articles and documents

An efficient procedure for the preparation of 1-nitroanthraquinone

A novel and efficient method is developed for the selective mono nitration of anthraquinone (1). A mixture of fuming nitric acid, sulfuric acid and phosphoric acid in carbon tetrachloride is introduced as a new nitrating system for the high yield preparation of 1-nitroanthraquinone.

Separation of 1,5-dinitroanthraquinone and 1,8-dinitroanthraquinone

A process for separating 1,5-dinitroanthraquinone and 1,8-dinitroanthraquinone by heating a dinitroanthraquinone mixture, in a mixture of from 5 to 85 per cent by weight of N-methylpyrrolidone and from 95 to 15 per cent by weight of an organic liquid which boils at from 80° to 210° C and is miscible in all proportions with N-methylpyrrolidone, at from 60° to 180° C, and separating off the undissolved material, at the extraction temperature, after the solution equilibrium has been reached. The insoluble material contains more than 85 per cent by weight, and as a rule more than 90 per cent by weight, of 1,5-dinitroanthraquinone. From the extract, it is possible to isolate the dissolved 1,8-dinitroanthraquinone together with the dissolved 1,5-dinitroanthraquinone and any byproducts which may be present.

Preparation of pure 1,5-dinitroanthraquinone

A mixture of dinitroanthraquinones of which at least 35% is 1,5-dinitroanthraquinone is dissolved at elevated temperature in a halogenated aromatic hydrocarbon, a carboxylic acid nitrile or a cyclic sulphone and is thereafter cooled selectively to precipitate substantially pure 1,5-dinitroanthraquinone. Preferred solvents are 1-chloronaphthalene, sulpholane and adipic acid dinitrile. The temperature of dissolution ranges from about 120° C up to the boiling point and cooling is by about 10° to 200° C to a temperature not below about 0° C.