128-66-5

Basic information

• Product Name: Vat Yellow 4
• Synonyms: dibenzo[b,def]chrysene-7,14-dione;1',2',6',7'-Dibenzpyrene-7,14-quinone;DIBENZO(B)CHRYSENE-7,14-DIONE;C.I.VATYELLOW4;Vat yellow 4 (C.I. 59100);C.I.59100;Indanthren Printing Yellow GOK;Nihonthrene Golden Yellow GK
• CAS NO: 128-66-5
• Molecular Formula: C₂₄H₁₂O₂
• Molecular Weight: 332.35088
• EINECS: 204-903-2
• Mol File: 128-66-5.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 429.48°C (rough estimate)
• Flash Point: 219.9 °C
• Appearance: viscous orange liquid
• Density: 1.1459 (rough estimate)
• Vapor Pressure: 1.15E-14mmHg at 25°C
• Refractive Index: 1.4891 (estimate)
• Stability: Stable. Combustible. Incompatible with strong oxidizing agents.
• CAS DataBase Reference: Vat Yellow 4(CAS DataBase Reference)
• NIST Chemistry Reference: Vat Yellow 4(128-66-5)
• EPA Substance Registry System: Vat Yellow 4(128-66-5)

Safety Data

• Hazardous Substances Data: 128-66-5(Hazardous Substances Data)

Usage

Chemical Properties

viscous orange liquid

Uses

Vat Yellow 4 is a commercial dye used in textiles. Polyaromatic hydrocarbon with potential carcinogenic activity.Environmental toxin on US EPA Toxic Release Inventory list (TRI) list.

Preparation

(a) 3-Benzoylbenzanthrone?and Aluminium chloride and antioxidant for the closed-loop response; (b) 1,5-Dibenzoyl-2-naphthaene?in Aluminium chloride and sodium chloride were under existing closed-loop response.

General Description

Viscous orange liquid. Used for coloring of cotton, wool and cellulose acetate.

Air & Water Reactions

Water soluble.

Reactivity Profile

Vat Yellow 4 reacts very readily with reducing agents to give a colorless or nearly colorless product. Subsequent oxidation then restores the color.

Health Hazard

ACUTE/CHRONIC HAZARDS: When heated to decomposition Vat Yellow 4 emits acrid smoke and irritating fumes.

Fire Hazard

Vat Yellow 4 is probably combustible.

Properties and Applications

red light yellow. Yellow brown powder. Soluble in nitrobenzene, four hydrogenated naphthalene and dimethyl benzene, slightly soluble in acetone, ethanol, benzene, chloroform, o-chlorophenol, Pyridine and toluene. The strong sulfuric acid to red light purple, orange after diluted precipitation, in alkaline insurance powder is in stock for purplish red color; In the acidic insurance powder also in stock for golden brown. Can be used for the discharge printing of cotton, mainly used in the winter sun often dark cotton print, also suitable for silk and polyamide fiber dyeing. Standard Ironing Fastness Chlorine bleach Light Fastness Mercerized Oxygen bleach Soaping Fading Stain ISO 4-5 4-5 5-6 5 4-5 3-4 4 AATCC 5 5 4-5 5 4

Standard

Ironing Fastness

Fading

Stain

ISO

4-5

AATCC

5

InChI:InChI=1/C24H12O2/c25-23-17-7-3-1-5-13(17)15-9-11-20-22-16(10-12-19(23)21(15)22)14-6-2-4-8-18(14)24(20)26/h1-12H

Synthetic route

dibenz[a,h]pyrene (189-64-0) + Mangantriacetat → dibenzo[b,def]chrysene-7,14-dione (128-66-5) + Acetic acid dibenzo[b,def]chrysen-7-yl ester (141396-59-0) + Acetic acid 14-acetoxy-dibenzo[b,def]chrysen-7-yl ester (141396-63-6)

Conditions	Yield
In acetic acid; benzene at 40℃; for 4h;	A n/a B 47% C 10%
In acetic acid; benzene at 40℃; Rate constant;

4-(2-formylphenyl)-7H-benzo[de]anthracen-7-one → dibenzo[b,def]chrysene-7,14-dione (128-66-5)

Conditions	Yield
With tetrafluoroboric acid; Barluenga reagent In diethyl ether; dichloromethane at -60℃; for 18h;	31%

meta-dinitrobenzene (99-65-0) + 1,5-dibenzoylnaphthalene (83-80-7) → dibenzo[b,def]chrysene-7,14-dione (128-66-5)

Conditions	Yield
With aluminium trichloride; sodium chloride at 160℃;

1,5-dibenzoylnaphthalene (83-80-7) + sodium 3-nitrobenzenesulfonate (127-68-4) → dibenzo[b,def]chrysene-7,14-dione (128-66-5)

Conditions	Yield
With aluminium trichloride; sodium chloride at 160℃;

1,5-dibenzoylnaphthalene (83-80-7) → dibenzo[b,def]chrysene-7,14-dione (128-66-5)

Conditions	Yield
With aluminium trichloride; sodium chloride at 120 - 130℃; Einleiten von Luft oder Sauerstoff;
With aluminium trichloride; sodium chloride at 120 - 130℃; Einleiten von Luft oder Sauerstoff;
With aluminium trichloride at 170 - 195℃;

3-benzoyl-benz[de]anthracen-7-one (6535-66-6) → dibenzo[b,def]chrysene-7,14-dione (128-66-5)

Conditions	Yield
With aluminium trichloride; sodium chloride at 120 - 130℃; Einleiten von Luft oder Sauerstoff;
With aluminium trichloride at 180℃;
With aluminium trichloride; sodium chloride at 120 - 130℃; Einleiten von Luft oder Sauerstoff;

1,5-dibenzoyl-4,8-dichloro-naphthalene → dibenzo[b,def]chrysene-7,14-dione (128-66-5)

Conditions	Yield
With quinoline; potassium hydroxide

1,5-dianthraniloyl-naphthalene → dibenzo[b,def]chrysene-7,14-dione (128-66-5)

Conditions	Yield
With hydrogenchloride Diazotization.Behandeln mit wss. H2O2 oder mit heisser wss. (oder aethanol.) Blei(IV)-acetat-Loesung;
With hydrogenchloride; water Diazotization.Bestrahlen mit UV-Licht;

1-benzoylnaphthalene (642-29-5) + benzoyl chloride (98-88-4) → dibenzo[b,def]chrysene-7,14-dione (128-66-5)

Conditions	Yield
With aluminium trichloride at 115 - 130℃;
With aluminium trichloride; sodium chloride at 115 - 130℃;

7H-benz[d,e]anthracene-7-one (82-05-3) + benzoyl chloride (98-88-4) → dibenzo[b,def]chrysene-7,14-dione (128-66-5)

Conditions	Yield
With aluminium trichloride; sodium 3-nitrobenzenesulfonate
With aluminium trichloride; zinc(II) chloride at 155℃;
With aluminium trichloride at 115 - 120℃;

1-benzoylnaphthalene (642-29-5) + benzoic acid anhydride (93-97-0) → dibenzo[b,def]chrysene-7,14-dione (128-66-5)

Conditions	Yield
With aluminium trichloride at 115 - 130℃;
With aluminium trichloride; sodium chloride at 115 - 130℃;

7H-benz[d,e]anthracene-7-one (82-05-3) + benzoic acid anhydride (93-97-0) → dibenzo[b,def]chrysene-7,14-dione (128-66-5)

Conditions	Yield
With aluminium trichloride
With aluminium trichloride; sodium chloride at 120 - 130℃;

7,14-dioxo-7,14-dihydro-dibenzo[b,def]chrysene-2,3-dicarboxylic acid anhydride (4378-57-8) → dibenzo[b,def]chrysene-7,14-dione (128-66-5)

Conditions	Yield
With quinoline; copper; copper(l) chloride Heating;

1.5-bis-<2-bromo-benzoyl>-naphthalene → dibenzo[b,def]chrysene-7,14-dione (128-66-5)

Conditions	Yield
With sodium cyanide at 350℃;
With potassium acetate at 350℃;
With sodium carbonate at 350℃;
With potassium phtalimide at 350℃;
With quinoline; potassium hydroxide

1.5-bis-<2-chloro-benzoyl>-naphthalene → dibenzo[b,def]chrysene-7,14-dione (128-66-5)

Conditions	Yield
With sodium cyanide at 350℃;
With potassium acetate at 350℃;
With sodium carbonate at 350℃;
With potassium phtalimide at 350℃;

aluminium trichloride (7446-70-0) + 1,5-dibenzoylnaphthalene (83-80-7) → dibenzo[b,def]chrysene-7,14-dione (128-66-5)

Conditions	Yield
at 170 - 195℃;

aluminium trichloride (7446-70-0) + 3-benzoyl-benz[de]anthracen-7-one (6535-66-6) → dibenzo[b,def]chrysene-7,14-dione (128-66-5)

Conditions	Yield
at 180℃;

2-formylbenzene boronic acid (40138-16-7) → dibenzo[b,def]chrysene-7,14-dione (128-66-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: 47 percent / Pd(PPh3)4; K3PO4 / 1,2-dimethoxy-ethane / 48 h / 80 °C 2: 74 percent / IPy2BF4; HBF4 / CH2Cl2; diethyl ether / 20 h / -60 °C 3: 31 percent / IPy2BF4; HBF4 / CH2Cl2; diethyl ether / 18 h / -60 °C View Scheme

2,2'-(naphthalene-1,5-diyl)dibenzaldehyde (898821-48-2) → dibenzo[b,def]chrysene-7,14-dione (128-66-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 74 percent / IPy2BF4; HBF4 / CH2Cl2; diethyl ether / 20 h / -60 °C 2: 31 percent / IPy2BF4; HBF4 / CH2Cl2; diethyl ether / 18 h / -60 °C View Scheme

C28H24O4 → dibenzo[b,def]chrysene-7,14-dione (128-66-5) + Benzindeno<2,1-b>anthracen-8,10-dion (27921-59-1)

Conditions	Yield
With methanesulfonic acid; trifluorormethanesulfonic acid at 140℃; Friedel-Crafts Acylation;

dibenzo[b,def]chrysene-7,14-dione (128-66-5) + tris-iso-propylsilyl acetylene (89343-06-6) → 7,14-bis((triisopropylsilyl)ethynyl)dibenzo[b,def ]chrysene (1201792-81-5)

Conditions	Yield
Stage #1: tris-iso-propylsilyl acetylene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.533333h; Inert atmosphere; Stage #2: dibenzo[b,def]chrysene-7,14-dione In tetrahydrofuran; hexane at -78 - 20℃; for 16h; Inert atmosphere; Stage #3: With hydrogenchloride; tin(ll) chloride In tetrahydrofuran; hexane; water at 20℃; for 2h; Inert atmosphere;	60%

dibenzo[b,def]chrysene-7,14-dione (128-66-5) + trimethylsilylacetylene (1066-54-2) → 7,14-bis((trimethylsilyl)ethynyl)dibenzo[b,def]chrysene

Conditions	Yield
Stage #1: trimethylsilylacetylene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.533333h; Inert atmosphere; Stage #2: dibenzo[b,def]chrysene-7,14-dione In tetrahydrofuran; hexane at -78 - 20℃; for 16h; Inert atmosphere; Stage #3: With hydrogenchloride; tin(ll) chloride In tetrahydrofuran; hexane; water at 20℃; for 2h; Inert atmosphere;	45%

dibenzo[b,def]chrysene-7,14-dione (128-66-5) + 2-ethynyl-1,1,1,3,3,3-hexamethyl-2-(trimethylsilyl)trisilane (73022-81-8) → 7,14-bis(tris(trimethylsilyl)ethynyl)dibenzo[b,def]chrysene

Conditions	Yield
Stage #1: 2-ethynyl-1,1,1,3,3,3-hexamethyl-2-(trimethylsilyl)trisilane With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.533333h; Inert atmosphere; Stage #2: dibenzo[b,def]chrysene-7,14-dione In tetrahydrofuran; hexane at -78 - 20℃; for 16h; Inert atmosphere; Stage #3: With hydrogenchloride; tin(ll) chloride In tetrahydrofuran; hexane; water at 20℃; for 2h; Inert atmosphere;	43%

2-triethylsilylacetylene (1777-03-3) + dibenzo[b,def]chrysene-7,14-dione (128-66-5) → 7,14-bis((triethylsilyl)ethynyl)dibenzo[b,def ]chrysene (1201792-82-6)

Conditions	Yield
Stage #1: 2-triethylsilylacetylene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.533333h; Inert atmosphere; Stage #2: dibenzo[b,def]chrysene-7,14-dione In tetrahydrofuran; hexane at -78 - 20℃; for 16h; Inert atmosphere; Stage #3: With hydrogenchloride; tin(ll) chloride In tetrahydrofuran; hexane; water at 20℃; for 2h; Inert atmosphere;	42%

2,2-dimethyl-3-butyne (917-92-0) + dibenzo[b,def]chrysene-7,14-dione (128-66-5) → 7,14-bis((tertbutyl)ethynyl)dibenzo[b,def]chrysene

Conditions	Yield
Stage #1: 3,3-Dimethylbut-1-yne With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.533333h; Inert atmosphere; Stage #2: dibenzo[b,def]chrysene-7,14-dione In tetrahydrofuran; hexane at -78 - 20℃; for 16h; Inert atmosphere; Stage #3: With hydrogenchloride; tin(ll) chloride In tetrahydrofuran; hexane; water at 20℃; for 2h; Inert atmosphere;	37%

(tert-butyldimethylsilyl)acetylene (86318-61-8) + dibenzo[b,def]chrysene-7,14-dione (128-66-5) → 7,14-bis((tertbutyldimethylsilyl)ethynyl)dibenzo[b,def]chrysene

Conditions	Yield
Stage #1: (tert-butyldimethylsilyl)acetylene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.533333h; Inert atmosphere; Stage #2: dibenzo[b,def]chrysene-7,14-dione In tetrahydrofuran; hexane at -78 - 20℃; for 16h; Inert atmosphere; Stage #3: With hydrogenchloride; tin(ll) chloride In tetrahydrofuran; hexane; water at 20℃; for 2h; Inert atmosphere;	34%

dibenzo[b,def]chrysene-7,14-dione (128-66-5) → indeno[123-cd]fluoranthene (193-43-1) + 13H-naphto<3,2,1-cd>fluoranthene-13-one (13227-56-0)

Conditions	Yield
at 1200℃;	A 17% B 4.5%
at 1200℃; Product distribution; further temp., vacuum flow app.;	A 17% B 4.5%

dibenzo[b,def]chrysene-7,14-dione (128-66-5) → dibenzo[b,def]chrysene-7,14-diol (36867-56-8)

Conditions	Yield
With sodium hydroxide; nickel at 55℃; Hydrogenation;

dibenzo[b,def]chrysene-7,14-dione (128-66-5) + hydrogen iodide (10034-85-2) + red phosphorus → 7,14-dihydro-dibenzo[b,def]chrysene (7350-86-9)

Conditions	Yield
at 190 - 200℃;

dibenzo[b,def]chrysene-7,14-dione (128-66-5) + zinc-powder → dibenz[a,h]pyrene (189-64-0)

dibenzo[b,def]chrysene-7,14-dione (128-66-5) + zinc-powder + water containing ZnCl2 + NaCl → dibenz[a,h]pyrene (189-64-0)

Conditions	Yield
at 280℃;

dibenzo[b,def]chrysene-7,14-dione (128-66-5) + zinc-powder + water containing ZnCl2 + NaCl → 7,14-dihydro-dibenzo[b,def]chrysene (7350-86-9) + dibenz[a,h]pyrene (189-64-0)

Conditions	Yield
at 280℃;

Upstream product

• 99-65-0 meta-dinitrobenzene 
• 83-80-7 1,5-dibenzoylnaphthalene 
• 127-68-4 sodium 3-nitrobenzenesulfonate 
• 642-29-5 1-benzoylnaphthalene 
• 98-88-4 benzoyl chloride 
• 82-05-3 7H-benz[d,e]anthracene-7-one 
• 93-97-0 benzoic acid anhydride 
• 898821-48-2 2,2'-(naphthalene-1,5-diyl)dibenzaldehyde 
• 40138-16-7 2-formylbenzene boronic acid 
• 7446-70-0 aluminium trichloride 
• 6535-66-6 3-benzoyl-benz[de]anthracen-7-one 
• 189-64-0 dibenz[a,h]pyrene 
• 4378-57-8 7,14-dioxo-7,14-dihydro-dibenzo[b,def]chrysene-2,3-dicarboxylic acid anhydride 

Downstream Products

• 7350-86-9 7,14-dihydro-dibenzo[b,def]chrysene 
• 189-64-0 dibenz[a,h]pyrene 
• 193-43-1 indeno[123-cd]fluoranthene 
• 13227-56-0 13H-naphto<3,2,1-cd>fluoranthene-13-one 

Relevant articles and documents

Temperature-mediated polymorphism in molecular crystals: The impact on crystal packing and charge transport

We report a novel synthesis to ultra high purity 7,14-bis((trimethylsilyl)ethynyl)dibenzo[b,def]-chrysene (TMS-DBC) and the use of this material in the growth of single crystals by solution and vapor deposition techniques. We observe that the substrate temperature has a dramatic impact on the crystal growth, producing two distinct polymorphs of TMS-DBC; low temperature (LT) fine red needles and high temperature (HT) large yellow platelets. Single crystal X-ray crystallography confirms packing structures where the LT crystals form a 1D slipped-stack structure, while the HT crystals adopt a 2D brickwork motif. These polymorphs also represent a rare example where both are extremely stable and do not interconvert to the other crystal structure upon solvent or thermal annealing. Single crystal organic field-effect transistors of the LT and HT crystals show that the HT 2D brickwork motif produces hole mobilities as high as 2.1 cm2 V-1 s-1, while the mobility of the 1D structure is significantly lower, at 0.028 cm2 V-1 s-1. Electronic-structure calculations indicate that the superior charge transport in the brickwork polymorph in comparison to the slipped-stack polymorph is due to the presence of an increased dimensionality of the charge migration pathways.

One-Electron Oxidation of Dibenzopyrenes by Manganic Acetate

The dibenzopyrenes (DBPs) are carcinogenic polycyclic aromatic hydrocarbons (PAH) found as environmental pollutants.DBP is the most potent carcinogenic PAH ever tested.To investigate the bioactivation of DBPs by one-electron oxidation, oxidation of DBP, DBP, DBP, DBP, and anthanthrene with Mn(OAc)3 was conducted and compared to that of benzopyrene (BP).All five DBPs produced monoacetoxy derivatives, and all of them except DBP also produced diacetoxy derivatives.Kinetic studies of the formation of monoacetoxy and diacetoxy derivatives of DBPs were carried out and the results were compared to those of the parent compound BP.DBP was similar to BP.DBP reacted inefficiently to form monoacetoxy and diacetoxy products.The other three DBPs resembled one another.These results provide preliminary essential information for studies of the bioactivation of the very potent carcinogen DBP to form DNA adducts.