128-58-5

Basic information

• Product Name: Vat Green 1
• Synonyms: 1,2-cde]benzo[rst]pentaphene-5,10-dione,16,17-dimethoxy-anthra[;16,17-dimethoxy-violanthron;2,3-cd:3’,2’,1’-lm)perylene-5,10-dione,16,17-dimethoxy-dinaphtho(;ahcovatjadegreenb;ahcovatjadegreenbda;ahcovatprintingjadegreenb;ahcovatprintingjadegreenbda;amanthrenebrilliantgreenj
• CAS NO: 128-58-5
• Molecular Formula: C₃₆H₂₀O₄
• Molecular Weight: 516.54
• EINECS: 204-896-6
• Product Categories: Organics
• Mol File: 128-58-5.mol
• Article Data: 0

Chemical Properties

• Boiling Point: 521.39°C (rough estimate)
• Appearance: solid
• Density: 1.1534 (rough estimate)
• Refractive Index: 1.4760 (estimate)
• Stability: Stable. Incompatible with strong oxidizing agents.
• CAS DataBase Reference: Vat Green 1(CAS DataBase Reference)
• NIST Chemistry Reference: Vat Green 1(128-58-5)
• EPA Substance Registry System: Vat Green 1(128-58-5)

Safety Data

• Hazardous Substances Data: 128-58-5(Hazardous Substances Data)

Usage

Chemical Properties

solid

Uses

16,17-Dimethoxyanthra[9,1,2-cde]-benzo[rst]pentaphene-5,10-dione is used in producing colored fibrous materials.

Preparation

(a) In nitrobenzene lieutenant Dinaphtho[1,2,3-cd:3′,2′,1′-lm]perylene-5,10-dione oxidation products were methylated; (b) will be 2-Methoxy-7H-benzo[de]anthracen-7-one?with Potassium hydroxide to alkali fusion; (C) will Benzanthrone in sulfuric acid with manganese dioxide oxidation, then use Potassium hydroxide Etanol solution condensation, then methylation; (d) will be 16,17-Dihydroxyviolanthrone methylation.

Flammability and Explosibility

Notclassified

Properties and Applications

brilliant green. Variegated dark green powder. Insoluble in water, Etanol, Chloroform and Toluene, soluble in hot 1, 2, 3, 4 – Tetrahydronaphthalene, slightly soluble in Acetone, 2 – Chlorophenol, Nitrobenzene and heat Pyridine . Alkaline reduction leuco for blue; Acid reduction leuco for brilliant red. In concentrated sulfuric acid to red light purple, green precipitation after dilution. Main use + cotton fiber dyeing and printing, also can be used for polyester/cotton blended fabric dyeing, the leuco is mainly used for cotton knits dyeing, but also can be used for plastic, soap and paper coloring. Standard Ironing Fastness Chlorine bleach Light Fastness Mercerized Oxygen bleach Soaping Fading Stain ISO 1 4 7 4-5 4-5 4-5 4-5 AATCC 4-5 4-5 6-7 4 4-5

Standard

Ironing Fastness

Fading

Stain

ISO

1

AATCC

4-5

InChI:InChI=1/C36H22O4/c1-39-27-15-25-17-7-3-5-9-21(17)35(37)23-13-11-19-20-12-14-24-30-26(18-8-4-6-10-22(18)36(24)38)16-28(40-2)34(32(20)30)33(27)31(19)29(23)25/h3-16,19,25H,1-2H3/t19?,25-/m0/s1

Synthetic route

2-methoxy-benz[de]anthracen-7-one (6535-67-7) → Jade Green XBN (128-58-5)

Conditions	Yield
With potassium hydroxide; ethanol at 130 - 140℃; Behandeln des Reaktionsprodukts mit Luft;
With potassium hydroxide; potassium chlorate; potassium acetate at 125℃; Reagens 4:Methanol; Reagens 5:Naphtalin; anschlissendes Erhitzen auf 200grad und Behandeln einer Suspension des Reaktionsprodukts in Wasser mit Luft;

isoviolanthrone (116-71-2) + methyl p-toluene sulfonate (80-48-8) → Jade Green XBN (128-58-5)

Conditions	Yield
With tetralin; sodium carbonate auf Siedetemperatur;
With potassium carbonate; 1,2,3-trichlorobenzene unter Zusatz von Phenol, Naphthol-(1) oder Hydrochinon auf 180grad;
With sodium carbonate; 1,2,3-trichlorobenzene unter Zusatz von Phenol, Naphthol-(1) oder Hydrochinon auf 180grad;

isoviolanthrone (116-71-2) + dimethyl sulfate (77-78-1) → Jade Green XBN (128-58-5)

Conditions	Yield
With potassium carbonate; 1,2,3-trichlorobenzene unter Zusatz von Phenol, Naphthol-(1) oder Hydrochinon auf 180grad;
With sodium carbonate; 1,2,3-trichlorobenzene unter Zusatz von Phenol, Naphthol-(1) oder Hydrochinon auf 180grad;

dimethyl sulfate (77-78-1) + 16.17-dihydroxy-violanthrenedione-(5.10) → Jade Green XBN (128-58-5)

Conditions	Yield
With potassium carbonate; nitrobenzene

dimethyl sulfate (77-78-1) + bz2.bz2'-dioxy-violanthrone → Jade Green XBN (128-58-5)

Conditions	Yield
With sodium carbonate; nitrobenzene

sulfuric acid (7664-93-9) + 16,17-dimethoxy-anthra[9,1,2-cde]benzo[rst]pentaphene-5,10-diol (3951-01-7) → Jade Green XBN (128-58-5)

5,10-bis-(5-carboxy-valeryloxy)-16,17-dimethoxy-anthra[9,1,2-cde]benzo[rst]pentaphene + aqueous alkaline solution + air → Jade Green XBN (128-58-5)

cyclopentyl nitrite (67764-33-4) + 5,10-bis-(5-carboxy-valeryloxy)-16,17-dimethoxy-anthra[9,1,2-cde]benzo[rst]pentaphene + aqueous alkaline solution + mineral acid → Jade Green XBN (128-58-5)

maleic anhydride (108-31-6) + Jade Green XBN (128-58-5) → (16.17-dimethoxy-anthra[9.1.2-cde]benzo[rst]pentaphenediyl-(5.10))-bis-hydrogen maleate

Conditions	Yield
With pyridine; copper at 70℃; unter Kohlendioxyd; anschliessendes Erwaermen auf 100grad;

Jade Green XBN (128-58-5) → 16,17-dimethoxy-anthra[9,1,2-cde]benzo[rst]pentaphene-5,10-diol (3951-01-7)

Conditions	Yield
With sodium hydroxide; sodium dithionite at 50℃;
With sodium hydroxide; sodium dithionite; sodium hydrogensulfite at 55 - 60℃;

Jade Green XBN (128-58-5) → 16,17-dimethoxy-5,10-bis-sulfooxy-anthra[9,1,2-cde]benzo[rst]pentaphene (2678-71-9)

Conditions	Yield
With pyridine; chlorosulphuric acid; hydrogen sulfide at 50℃;
With pyridine; sodium sulfide anschliessendes Behandeln mit Chloroschwefelsaeure, zuletzt bei 45grad;
With sodium hydroxide; sodium dithionite anschliessendes Behandeln mit Sulfo-trimethyl-ammonium-betain;

Jade Green XBN (128-58-5) → 5,10-bis-(hydroxy-m-tolyloxy-phosphoryloxy)-16,17-dimethoxy-anthra[9,1,2-cde]benzo[rst]pentaphene

Conditions	Yield
With sodium hydroxide; sodium dithionite anschliessendes Behandeln mit Phosphorsaeure-m-tolylester-dichlorid;

Jade Green XBN (128-58-5) + chloroformic acid ethyl ester (541-41-3) → 5,10-bis-ethoxycarbonyloxy-16,17-dimethoxy-anthra[9,1,2-cde]benzo[rst]pentaphene

Conditions	Yield
With pyridine; zinc at 80 - 130℃;

Jade Green XBN (128-58-5) + Adipic acid dichloride (111-50-2) → 5,10-bis-(5-carboxy-valeryloxy)-16,17-dimethoxy-anthra[9,1,2-cde]benzo[rst]pentaphene

Conditions	Yield
With pyridine; copper zuletzt bei 50grad;

1-methyl-4-nitrosobenzene (623-11-0) + Jade Green XBN (128-58-5) + sodium hydrogensulfite + Na2S2O4 → 16,17-dimethoxy-anthra[9,1,2-cde]benzo[rst]pentaphene-5,10-diol (3951-01-7)

Conditions	Yield
at 60℃;

Jade Green XBN (128-58-5) → 16,17-bis(hexyloxy)-anthra[9,1,2-cde-]benzo[rst]pentaphene-5,10-dione (25637-03-0)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: dichloromethane / 1 h / 20 °C 1.2: 16 h / 20 °C / Reflux; Cooling with ice 2.1: potassium carbonate; 18-crown-6 ether / N,N-dimethyl-formamide / 12 h / 80 °C View Scheme

Jade Green XBN (128-58-5) → 16,17-dihydroxyviolanthrene-5,10-dione (128-59-6)

Conditions	Yield
Stage #1: Jade Green XBN In dichloromethane at 20℃; for 1h; Stage #2: With boron tribromide In dichloromethane at 20℃; for 16h; Reflux; Cooling with ice;

Jade Green XBN (128-58-5) → 16,17-didecyloxyviolanthrone

Conditions	Yield
Multi-step reaction with 2 steps 1.1: dichloromethane / 1 h / 20 °C 1.2: 16 h / 20 °C / Reflux; Cooling with ice 2.1: potassium carbonate; 18-crown-6 ether / N,N-dimethyl-formamide / 5 h / 80 °C View Scheme

Jade Green XBN (128-58-5) → 16,17-bis(octyloxy)-anthra[9,1,2-cde-]benzo[rst]pentaphene-5,10-dione (85652-50-2)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: dichloromethane / 1 h / 20 °C 1.2: 16 h / 20 °C / Reflux; Cooling with ice 2.1: potassium carbonate; 18-crown-6 ether / 1-methyl-pyrrolidin-2-one / 8 h / 100 °C View Scheme

Upstream product

• 116-71-2 isoviolanthrone 
• 77-78-1 dimethyl sulfate 
• 67764-33-4 cyclopentyl nitrite 
• 7664-93-9 sulfuric acid 
• 3951-01-7 16,17-dimethoxy-anthra[9,1,2-cde]benzo[rst]pentaphene-5,10-diol 
• 80-48-8 methyl p-toluene sulfonate 
• 6535-67-7 2-methoxy-benz[de]anthracen-7-one 

Downstream Products

• 85652-50-2 16,17-bis(octyloxy)-anthra[9,1,2-cde-]benzo[rst]pentaphene-5,10-dione 
• 71550-33-9 16,17-didecyloxyviolanthrone 
• 128-59-6 16,17-dihydroxyviolanthrene-5,10-dione 
• 2678-71-9 16,17-dimethoxy-5,10-bis-sulfooxy-anthra[9,1,2-cde]benzo[rst]pentaphene