128-64-3

Basic information

• Product Name: Vat Violet 10
• Synonyms: Benzadone Violet B;Benzo[rst]phenanthro[10,1,2-cde]pentaphene-9,18-dione;C.I. 60000;C.I. Vat Violet 10;Carbanthrene Printing Violet 2R;Dinaphtho(1,2,3-cd:1',2',3'-lm)perylene-9,18-dione;Isothrene;Isoviolanthrone A
• CAS NO: 128-64-3
• Molecular Formula: C₃₄H₁₆O₂
• Molecular Weight: 456.49
• EINECS: 204-901-1
• Product Categories: Organics
• Mol File: 128-64-3.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• Density: 1.487g/cm³
• Refractive Index: 1.926
• Solubility: slightly sol. in Acetone,Toluene,Chloroform
• CAS DataBase Reference: Vat Violet 10(CAS DataBase Reference)
• NIST Chemistry Reference: Vat Violet 10(128-64-3)
• EPA Substance Registry System: Vat Violet 10(128-64-3)

Safety Data

• Hazardous Substances Data: 128-64-3(Hazardous Substances Data)

Usage

Preparation

commonly known as Isoviolanthrone.(a) 7H-benzo[de]anthracen-7-one?chlorinated, with Potassium hydroxide of Etanol solution treatment; (b) 7H-benzo[de]anthracen-7-one?and Potassium hydroxide of Etanol solution in Xylene, Chlorobenzene or kerosene in heating; (c) 3-Chloro-7H-benzo[de]anthracen-7-one?the anthrone into corresponding sulfide or selenide and then use alkali treatment.

Properties and Applications

blue light purple. Soluble in 2 – Chlorophenol, Xylene to red, fluorescence, slightly soluble in Acetone, Chloroform, Pyridine and Toluene, insoluble in Etanol. In concentrated sulfuric acid for SAP green, purple precipitation after dilution, In the basic insurance powder solution for dark red light blue, in acid insurance powder solution for wine. Standard Ironing Fastness Chlorine bleach Light Fastness Mercerized Oxygen bleach Soaping Fading Stain ISO 3 5 5-6 4 4-5

Standard

Ironing Fastness

Fading

Stain

ISO

3

Purification Methods

Dissolve isoviolanthrone in 98% H2SO4 and precipitate it by adding water to reduce the acid concentration to about 90%. It sublimes in vacuo to give dark green-violet needles [Parkyns & Ubblehode J Chem Soc 4188 1960]. [Beilstein 7 I 465, 7 II 815, 7 III 4538, 7 IV 2747.]

InChI:InChI=1/C34H16O2/c35-33-25-7-3-1-5-17(25)19-9-11-21-24-14-16-28-32-20(18-6-2-4-8-26(18)34(28)36)10-12-22(30(24)32)23-13-15-27(33)31(19)29(21)23/h1-16H

Synthetic route

7H-benz[d,e]anthracene-7-one (82-05-3) → isoviolanthrone (128-64-3)

Conditions	Yield
With 2,6-dichloro-benzonitrile; potassium tert-butylate at 170℃;	95%
With potassium hydroxide; ethanol at 130℃; weitere Reagentien: Kerosin, Chlorbenzol;
With potassium hydroxide; isopropyl alcohol at 130℃; weitere Reagentien: Kerosin, Chlorbenzol;

3-bromobenzanthrone (81-96-9) → isoviolanthrone (128-64-3)

Conditions	Yield
With potassium ethoxide In ethanol at 150 - 160℃; for 2h;	70%
With sodium ethanolate at 120 - 130℃;

7H-benz[d,e]anthracene-7-one (82-05-3) + 3-chloro-7H-benzo(de)anthracen-7-one (6409-44-5) + sodium ethanolate (141-52-6) → isoviolanthrone (128-64-3)

Conditions	Yield
at 105 - 110℃;

7H-benz[d,e]anthracene-7-one (82-05-3) + 3-chloro-7H-benzo(de)anthracen-7-one (6409-44-5) → isoviolanthrone (128-64-3)

Conditions	Yield
With potassium hydroxide; sodium ethanolate; xylene at 70 - 75℃;
With potassium hydroxide; isopropyl alcohol; benzene at 10 - 15℃;
With sodium ethanolate at 105 - 110℃;

7H-benz[d,e]anthracene-7-one (82-05-3) + 3-bromobenzanthrone (81-96-9) + sodium ethanolate (141-52-6) → isoviolanthrone (128-64-3)

Conditions	Yield
at 105 - 110℃;
at 105 - 110℃; nachfolgend Einw. von Luft;

7H-benz[d,e]anthracene-7-one (82-05-3) + 3-bromobenzanthrone (81-96-9) → isoviolanthrone (128-64-3)

Conditions	Yield
With potassium hydroxide; sodium ethanolate; xylene at 70 - 75℃;
With potassium hydroxide; isopropyl alcohol; benzene at 10 - 15℃;
With sodium ethanolate at 105 - 110℃;

7H-benz[d,e]anthracene-7-one (82-05-3) + 3-p-tolylsulfanyl-benz[de]anthracen-7-one (81232-52-2) + sodium ethanolate (141-52-6) → isoviolanthrone (128-64-3)

Conditions	Yield
at 105 - 110℃;

7H-benz[d,e]anthracene-7-one (82-05-3) → isoviolanthrone (116-71-2) + isoviolanthrone (128-64-3)

Conditions	Yield
With methanol; potassium hydroxide
With methanol; potassium hydroxide at 170 - 180℃; Behandeln des Reaktionsprodukts mit Luft;
With potassium hydroxide; ethanol at 170 - 180℃; Behandeln des Reaktionsprodukts mit Luft;

3-chloro-7H-benzo(de)anthracen-7-one (6409-44-5) → isoviolanthrone (128-64-3)

Conditions	Yield
With potassium hydroxide; isopropyl alcohol; benzene at 10 - 15℃;
With potassium hydroxide; benzaldehyde; 1,2,3-trichlorobenzene at 80 - 90℃;
With potassium hydroxide; ethanol; sodium at 145℃;

3-bromobenzanthrone (81-96-9) + sodium ethanolate (141-52-6) → isoviolanthrone (128-64-3)

Conditions	Yield
at 120 - 130℃; Behandeln mit Luft;

4,4'-dibenzanthronyl (116-90-5) → isoviolanthrone (116-71-2) + isoviolanthrone (128-64-3)

Conditions	Yield
With potassium hydroxide at 190℃; nachfolgend Behandeln mit Luft;

3,9-dibromo-7h-benz(de)anthracen-7-one (81-98-1) → isoviolanthrone (128-64-3)

Conditions	Yield
With potassium hydroxide at 140 - 150℃; nachfolgend Behandeln mit Luft;

isoviolanthrene A (188-84-1) → isoviolanthrone (128-64-3)

Conditions	Yield
With nitric acid

3,9-dibenzoyl-perylene (26556-97-8) → isoviolanthrone (128-64-3)

Conditions	Yield
With manganese(III) sulfate; boric acid at -15 - -10℃; weiteres Reagens: konz. Schwefelsaeure;
With manganese(IV) oxide; boric acid at -15 - -10℃; weiteres Reagens: konz. Schwefelsaeure;
With aluminium trichloride at 150 - 195℃;

[3,4']bi[benz[de]anthracenyl]-7,7'-dione (5233-86-3) → isoviolanthrone (128-64-3)

Conditions	Yield
With potassium hydroxide at 125 - 140℃;
With sodium anilide; aniline at 140 - 150℃;
With potassium hydroxide at 125 - 140℃;

3'-fluoro-[3,4']bi[benz[de]anthracenyl]-7,7'-dione (361-13-7) → isoviolanthrone (128-64-3)

Conditions	Yield
beim Erhitzen ueber den Schmelzpunkt;
With potassium hydroxide at 110 - 125℃; nachfolgend Behandeln mit Luft;
beim Erhitzen ueber den Schmelzpunkt;

3,9-bis-(2-chloro-benzoyl)-perylene (858857-42-8) → isoviolanthrone (128-64-3)

Conditions	Yield
With aluminium trichloride at 170℃;
With quinoline; potassium hydroxide

3,9-dibenzoyl-4,10-dichloro-perylene (856340-87-9) → isoviolanthrone (128-64-3)

Conditions	Yield
With aluminium trichloride at 170℃;
With potassium hydroxide; aniline
With quinoline; potassium hydroxide

3,9-dibenzoyl-4,10-dibromo-perylene (856340-89-1) → isoviolanthrone (128-64-3)

Conditions	Yield
With aluminium trichloride at 170℃;
With potassium hydroxide; aniline
With quinoline; potassium hydroxide

3-p-tolylsulfanyl-benz[de]anthracen-7-one (81232-52-2) + o-chlorobenzoyl chloride (609-65-4) → isoviolanthrone (128-64-3)

Conditions	Yield
Erhitzen des Reaktionsprodukts mit konz.Schwefelsaeure auf 130grad;
Erhitzen des Reaktionsprodukts mit konz.Schwefelsaeure auf 130grad;

3-phenoxy-benz[de]anthracen-7-one (84271-51-2) + o-chlorobenzoyl chloride (609-65-4) → isoviolanthrone (128-64-3)

Conditions	Yield
und nachfolgenden Erhitzen mit konz.Schwefelsaeure auf 140grad;

PERYLENE (198-55-0) + benzoyl chloride (98-88-4) → isoviolanthrone (128-64-3)

Conditions	Yield
With aluminium trichloride at 150℃;
With aluminium trichloride at 150℃;

3,9-dibromoperylene (56752-35-3) + benzoyl chloride (98-88-4) → isoviolanthrone (128-64-3)

Conditions	Yield
With aluminium trichloride at 150 - 170℃;

3-chloro-7H-benzo(de)anthracen-7-one (6409-44-5) + sodium anilide (1865-45-8) + aniline (62-53-3) → isoviolanthrone (128-64-3)

Conditions	Yield
at 25℃; nachfolgend Behandlung mit Luft;

[3,4']bi[benz[de]anthracenyl]-7,7'-dione (5233-86-3) + sodium anilide (1865-45-8) + aniline (62-53-3) → isoviolanthrone (128-64-3)

Conditions	Yield
at 140 - 150℃;
at 140 - 150℃;

7H-benz[d,e]anthracene-7-one (82-05-3) + sodium ethanolate (141-52-6) + bz 1-p-tolylsulfanyl-benzanthrone → isoviolanthrone (128-64-3)

Conditions	Yield
at 105 - 110℃;

methanol (67-56-1) + 7H-benz[d,e]anthracene-7-one (82-05-3) + potassium hydroxide → isoviolanthrone (128-64-3)

Conditions	Yield
at 170 - 180℃;

7H-benz[d,e]anthracene-7-one (82-05-3) + ethanol (64-17-5) + potassium hydroxide → isoviolanthrone (128-64-3)

Conditions	Yield
at 170 - 180℃;

7H-benz[d,e]anthracene-7-one (82-05-3) + 3-chloro-7H-benzo(de)anthracen-7-one (6409-44-5) + sodium ethanolate (141-52-6) + potassium hydroxide → isoviolanthrone (128-64-3)

Conditions	Yield
at 70 - 75℃; weitere Verbindung: Xylol;

7H-benz[d,e]anthracene-7-one (82-05-3) + 3-bromobenzanthrone (81-96-9) + sodium ethanolate (141-52-6) + potassium hydroxide → isoviolanthrone (128-64-3)

Conditions	Yield
at 70 - 75℃; weitere Verbindung: Xylol;

9-(iodomethyl)nonadecane (1043023-53-5) + isoviolanthrone (128-64-3) → C74H98O2 (1369591-71-8)

Conditions	Yield
Stage #1: isoviolanthrone With sodium dithionite; sodium hydroxide In tetrahydrofuran; water at 20℃; for 1h; Inert atmosphere; Sonication; Stage #2: 9-(iodomethyl)nonadecane In tetrahydrofuran at 80℃; for 40h; Inert atmosphere;	63%

isoviolanthrone (128-64-3) + dimethyl sulfate (77-78-1) → 9,18-dimethoxy-benzo[rst]phenanthro[10,12-cde]pentaphene

Conditions	Yield
Stage #1: isoviolanthrone With sodium dithionite; sodium hydroxide In tetrahydrofuran; water at 20℃; for 1h; Inert atmosphere; Sonication; Stage #2: dimethyl sulfate In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere;	60%

isoviolanthrone (128-64-3) + 5-(iodomethyl)undecane (1256345-37-5) → C58H66O2 (1369591-74-1)

Conditions	Yield
Stage #1: isoviolanthrone With sodium dithionite; sodium hydroxide In tetrahydrofuran; water at 20℃; for 1h; Inert atmosphere; Sonication; Stage #2: 5-(iodomethyl)undecane In tetrahydrofuran at 80℃; for 43h; Inert atmosphere;	59%

3-(iodomethyl)heptane (1653-16-3) + isoviolanthrone (128-64-3) → C50H50O2 (1369591-75-2)

Conditions	Yield
Stage #1: isoviolanthrone With sodium dithionite; sodium hydroxide In tetrahydrofuran; water at 20℃; for 1h; Inert atmosphere; Sonication; Stage #2: 3-(iodomethyl)heptane In tetrahydrofuran at 80℃; for 40h; Inert atmosphere;	48%

isoviolanthrone (128-64-3) + tris-iso-propylsilyl acetylene (89343-06-6) → C56H58Si2 (1243689-44-2)

Conditions	Yield
Stage #1: tris-iso-propylsilyl acetylene With n-butyllithium In tetrahydrofuran; hexane at 0 - 60℃; for 0.5h; Stage #2: isoviolanthrone In tetrahydrofuran; hexane at 20 - 60℃; for 2h; Stage #3: With hydrogenchloride; tin(ll) chloride In tetrahydrofuran; hexane; water at 60℃; for 0.5h;	8%
Stage #1: tris-iso-propylsilyl acetylene With n-butyllithium In tetrahydrofuran at 0℃; for 1h; Stage #2: isoviolanthrone In tetrahydrofuran at 0 - 20℃; Stage #3: With sodium hypophosphite monohydrate; acetic acid; sodium iodide for 4h; Reflux;

isoviolanthrone (128-64-3) → Vat Brilliant Violet RR (81-28-7)

Conditions	Yield
With sulfuryl dichloride; nitrobenzene at 50 - 60℃;
durch Chlorierung;
With chlorosulfonic acid; selenium
With chlorosulfonic acid; sodium selenite
With chlorine; nitrobenzene at 50 - 60℃;

isoviolanthrone (128-64-3) → naphtho[2,3-c]pentaphene-5,6,9,14,15,18-hexaone (872277-87-7)

Conditions	Yield
With potassium dichromate; sulfuric acid at 85 - 95℃;
With chromium(VI) oxide; acetic acid

isoviolanthrone (128-64-3) → 5,14-dibromo-benzo[rst]phenanthro[10,1,2-cde]pentaphene-9,18-dione

Conditions	Yield
With bromine at 150℃; unter Druck;
With bromine; nitrobenzene

isoviolanthrone (128-64-3) → 6,15-dihydroxy-benzo[rst]phenanthro[10,1,2-cde]pentaphene-9,18-dione (56275-97-9)

Conditions	Yield
With manganese(IV) oxide; sulfuric acid; boric acid at 60℃;
With manganese(IV) oxide; sulfuric acid
With manganese(IV) oxide; sulfuric acid at 20℃;

isoviolanthrone (128-64-3) → 6,15-dinitro-benzo[rst]phenanthro[10,1,2-cde]pentaphene-9,18-dione

Conditions	Yield
With nitric acid; acetic acid

Upstream product

• 81232-52-2 3-p-tolylsulfanyl-benz[de]anthracen-7-one 
• 609-65-4 o-chlorobenzoyl chloride 
• 84271-51-2 3-phenoxy-benz[de]anthracen-7-one 
• 82-05-3 7H-benz[d,e]anthracene-7-one 
• 141-52-6 sodium ethanolate 
• 67-56-1 methanol 
• 64-17-5 ethanol 
• 6409-44-5 3-chloro-7H-benzo(de)anthracen-7-one 
• 81-96-9 3-bromobenzanthrone 
• 67-63-0 isopropyl alcohol 
• 71-36-3 butan-1-ol 
• 386-24-3 3-fluoro-benz[de]anthracen-7-one 
• 91-22-5 quinoline 
• 858857-42-8 3,9-bis-(2-chloro-benzoyl)-perylene 

Downstream Products

• 7475-29-8 9,10-anthraquinone-1,2-dicarboxylic acid 
• 88-99-3 benzene-1,2-dicarboxylic acid 
• 65122-11-4 isoviolanthrone dichloride 
• 188-84-1 isoviolanthrene A 

Relevant articles and documents

-

-

-

-