224-41-9

Basic information

• Product Name: DIBENZO(A,J)ANTHRACENE
• Synonyms: 3,4,5,6-Dibenzanthracene;Dibenzo-1,2,7,8-anthracene;DIBENZO(A,J)ANTHRACENE;DIBENZ(A,J)ANTHRACENE;Dibenz[a,j]anthracene (purity);74798, Dibenz[a,j]anthracene (purity);Nsc90321;Wln: L E6 D6 B666j
• CAS NO: 224-41-9
• Molecular Formula: C₂₂H₁₄
• Molecular Weight: 278.35
• EINECS: 205-928-1
• Product Categories: Alphabetic;D;DIA - DIC
• Mol File: 224-41-9.mol
• Article Data: 14

Chemical Properties

• Melting Point: 197.5°C
• Boiling Point: 356.16°C (rough estimate)
• Flash Point: 264.5°C
• Appearance: /
• Density: 1.1489 (estimate)
• Vapor Pressure: 1.41E-10mmHg at 25°C
• Refractive Index: 1.8120 (estimate)
• Storage Temp.: 2-8°C
• Water Solubility: 8.629ug/L(25 oC)
• BRN: 2051201
• CAS DataBase Reference: DIBENZO(A,J)ANTHRACENE(CAS DataBase Reference)
• NIST Chemistry Reference: DIBENZO(A,J)ANTHRACENE(224-41-9)
• EPA Substance Registry System: DIBENZO(A,J)ANTHRACENE(224-41-9)

Safety Data

• Hazard Codes: T
• Statements: 25-36/37/38-52/53
• Safety Statements: 26-45-61
• RIDADR: 2811
• WGK Germany: 3
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 224-41-9(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 46, p. 2601, 1981 DOI: 10.1021/jo00325a041

Health Hazard

Dibenz[a,j]anthracene has shown to causeskin cancer in animals, producing tumor atthe site of application. There is no report ofits toxicity. It tested positive in a histidinereversion–Ames test.

InChI:InChI=1/C22H14/c1-3-7-19-15(5-1)9-11-17-13-18-12-10-16-6-2-4-8-20(16)22(18)14-21(17)19/h1-14H

Synthetic route

2,4',6',2''-tetravinyl-[1,1';3',1'']terphenyl (868847-77-2) → dibenz[a,j]anthracene (224-41-9)

Conditions	Yield
With Grubbs catalyst first generation In dichloromethane at 35℃; for 23h; ring-closing olefin metathesis;	98%

1,2,3,4,10,11,12,13-Octahydrodibenzanthracene (130799-92-7) → dibenz[a,j]anthracene (224-41-9)

Conditions	Yield
palladium on activated charcoal In various solvent(s) Heating;	93%

14-acetoxydibenzanthracene (81205-71-2) → dibenz[a,j]anthracene (224-41-9)

Conditions	Yield
With potassium hydroxide; zinc In 1,4-dioxane; water Heating;	90%

2-(Naphthalene-2-carbonyl)-naphthalene-1-carboxylic acid (77321-42-7) → dibenz[a,j]anthracene (224-41-9)

Conditions	Yield
With phosphorus; hydrogen iodide In acetic acid for 120h; Heating;	84%

3-Naphthalen-2-yl-3H-naphtho[1,2-c]furan-1-one (73540-68-8) → dibenz[a,j]anthracene (224-41-9)

Conditions	Yield
With hydrogen iodide; hypophosphorous acid In acetic acid for 240h; Heating;	80%

7-(Methylthio)-dibenzanthracene (134576-19-5) → dibenz[a,j]anthracene (224-41-9)

Conditions	Yield
With nickel In methanol for 6h; Ambient temperature;	78%

(E,E)-1,3-distyrylbenzene (1725-76-4) → benzo[c]chrysene (194-69-4) + dibenz[a,j]anthracene (224-41-9)

Conditions	Yield
With iodine In benzene for 1h; Irradiation;	A 70% B 8%
With iodine In benzene Irradiation;	A 70% B 8%

7,14-dihydro-14-ethoxy-7-(trimrthylsilyl)-7,14-epoxydibenzanthracene (103224-51-7) → dibenz[a,j]anthracene (224-41-9)

Conditions	Yield
With acetic acid; zinc for 14h; Heating;	55%

C28H22 (80992-42-3) → dibenz[a,j]anthracene (224-41-9) + C28H22 (82344-75-0) + C28H22 (80992-41-2)

Conditions	Yield
In benzene Irradiation; Yields of byproduct given;	A 39% B n/a C n/a
In benzene Irradiation; Yield given. Yields of byproduct given;

(2-methylnaphthalen-1-yl)(naphthalen-1-yl)methanone (41774-28-1) → dibenzo[a,h]anthracene (53-70-3) + dibenz[a,j]anthracene (224-41-9)

Conditions	Yield
at 420℃; for 0.75h;	A 20% B 2%

1-Methylnaphthalene (90-12-0) → picene (213-46-7) + dibenzo[a,h]anthracene (53-70-3) + Benzo[b]chrysene (214-17-5) + dibenz[a,j]anthracene (224-41-9)

Conditions	Yield
at 750℃;

5,6,8,9-Tetrahydrodibenzoanthracene (19399-64-5) → dibenz[a,j]anthracene (224-41-9)

Conditions	Yield
With carbon dioxide; palladium on activated charcoal at 300℃;

14H-dibenz[a,j]anthracen-7-one (41774-36-1) → dibenz[a,j]anthracene (224-41-9)

Conditions	Yield
With sodium hydroxide; zinc

1,2-dihydrocyclobutene[α]naphthalene (32277-35-3) → dibenzo[a,h]anthracene (53-70-3) + dibenz[a,j]anthracene (224-41-9)

Conditions	Yield
at 890℃;

C22H30O2 (130800-12-3) → dibenz[a,j]anthracene (224-41-9)

Conditions	Yield
With methanesulfonic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone 1.) CHCl3, r.t., 2.) benzene, reflux; Yield given. Multistep reaction;
Multi-step reaction with 2 steps 1: 1.) methanesulfonic acid, 2.) o-chloranil / 1.) CHCl3, r.t., 2.) benzene, reflux, 48 h 2: 93 percent / 10 percent Pd/C / various solvent(s) / Heating View Scheme

lithium salt of N,N-diethyl-1-naphthtamide (81194-74-3) + β-naphthaldehyde (66-99-9) → dibenz[a,j]anthracene (224-41-9)

Conditions	Yield
1.) diethyl ether, THF, -60 deg C 2.) Zn, KOH, pyridine, H2O, MeOH, reflux, 2.5 h 3.) ZnCl2, acetic acid, 30 min 4.) HI, hypophosphoric acid, 30 min; Yield given. Multistep reaction;

trans-9,10-dihydro-2-styrylphenanthrene (89988-22-7) → benzo[c]chrysene (194-69-4) + dibenz[a,j]anthracene (224-41-9)

Conditions	Yield
With iodine; 2,3-dicyano-5,6-dichloro-p-benzoquinone 1) benzene, irradiation, 7 h, 2) benzene, reflux, 14 h; Yield given. Multistep reaction. Yields of byproduct given;

carbon disulfide (75-15-0) + aluminium trichloride (7446-70-0) + 1-Chloromethylnaphthalene (86-52-2) + 1-chloromethylnaphthalene (2506-41-4) → dibenzo[a,h]anthracene (53-70-3) + benzo[a]naphthacene (226-88-0) + dibenz[a,j]anthracene (224-41-9)

Conditions	Yield
Erhitzen des Reaktionsprodukts mit Kupfer-Pulver, neben groessren Mengen makromolekularer Substanzen;

carbon disulfide (75-15-0) + aluminium trichloride (7446-70-0) + 1-Chloromethylnaphthalene (86-52-2) + 2-Methylnaphthalene (91-57-6) → dibenzo[a,h]anthracene (53-70-3) + benzo[a]naphthacene (226-88-0) + dibenz[a,j]anthracene (224-41-9)

Conditions	Yield
Erhitzen des Reaktionsprodukts mit Kupfer-Pulver;

7-oxo-7.14-dihydro-dibenzanthracene → dibenz[a,j]anthracene (224-41-9)

Conditions	Yield
With sodium hydroxide; zinc

dibenzanthracene-dicarboxylic acid-(6.8) → dibenz[a,j]anthracene (224-41-9)

Conditions	Yield
at 340 - 350℃; under 3 - 4 Torr;

1,5-dibromo-2,4-divinylbenzene (868847-74-9) → dibenz[a,j]anthracene (224-41-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 93 percent / tetrakis(triphenylphosphine)palladium(0); sodium carbonate / 1,2-dimethoxy-ethane; ethanol; H2O / 16 h / Heating 2: 98 percent / bis(tricyclohexylphosphine)(benzylidene)ruthenium dichloride / CH2Cl2 / 23 h / 35 °C View Scheme

1,5-dibromo-2,4-bis(dibromomethyl)benzene (58997-70-9) → dibenz[a,j]anthracene (224-41-9)

Conditions

Yield

Multi-step reaction with 4 steps 1.1: 96 percent / silver nitrate / ethanol; H2O / 0.5 h / Heating 2.1: potassium tert-butoxide / tetrahydrofuran / 0.08 h 2.2: 61 percent / tetrahydrofuran / 25 °C 3.1: 93 percent / tetrakis(triphenylphosphine)palladium(0); sodium carbonate / 1,2-dimethoxy-ethane; ethanol; H2O / 16 h / Heating 4.1: 98 percent / bis(tricyclohexylphosphine)(benzylidene)ruthenium dichloride / CH2Cl2 / 23 h / 35 °C View Scheme

1,5-dibromo-2,4-dimethylbenzene (615-87-2) → dibenz[a,j]anthracene (224-41-9)

Conditions

Yield

Multi-step reaction with 5 steps 1.1: 88 percent / N-bromosuccinimide / CCl4 / 9 h / Heating; irradiation 2.1: 96 percent / silver nitrate / ethanol; H2O / 0.5 h / Heating 3.1: potassium tert-butoxide / tetrahydrofuran / 0.08 h 3.2: 61 percent / tetrahydrofuran / 25 °C 4.1: 93 percent / tetrakis(triphenylphosphine)palladium(0); sodium carbonate / 1,2-dimethoxy-ethane; ethanol; H2O / 16 h / Heating 5.1: 98 percent / bis(tricyclohexylphosphine)(benzylidene)ruthenium dichloride / CH2Cl2 / 23 h / 35 °C View Scheme

2,4-dibromobenzene-1,5-dicarboxaldehyde (97094-37-6) → dibenz[a,j]anthracene (224-41-9)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: potassium tert-butoxide / tetrahydrofuran / 0.08 h 1.2: 61 percent / tetrahydrofuran / 25 °C 2.1: 93 percent / tetrakis(triphenylphosphine)palladium(0); sodium carbonate / 1,2-dimethoxy-ethane; ethanol; H2O / 16 h / Heating 3.1: 98 percent / bis(tricyclohexylphosphine)(benzylidene)ruthenium dichloride / CH2Cl2 / 23 h / 35 °C View Scheme

m-xylene (108-38-3) → dibenz[a,j]anthracene (224-41-9)

Conditions

Yield

Multi-step reaction with 6 steps 1.1: 58 percent / Br2; I2 / 16 h / 20 °C 2.1: 88 percent / N-bromosuccinimide / CCl4 / 9 h / Heating; irradiation 3.1: 96 percent / silver nitrate / ethanol; H2O / 0.5 h / Heating 4.1: potassium tert-butoxide / tetrahydrofuran / 0.08 h 4.2: 61 percent / tetrahydrofuran / 25 °C 5.1: 93 percent / tetrakis(triphenylphosphine)palladium(0); sodium carbonate / 1,2-dimethoxy-ethane; ethanol; H2O / 16 h / Heating 6.1: 98 percent / bis(tricyclohexylphosphine)(benzylidene)ruthenium dichloride / CH2Cl2 / 23 h / 35 °C View Scheme

1-Bromonaphthalene (90-11-9) + soda lime → dibenz[a,j]anthracene (224-41-9)

Conditions	Yield
Multi-step reaction with 2 steps 2: 55 percent / Zn, AcOH / 14 h / Heating View Scheme

7-(Methylthio)-5,6-dihydrodibenzanthracene (134576-15-1) → dibenz[a,j]anthracene (224-41-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 96 percent / DDQ / dioxane / 24 h / Heating 2: 78 percent / Raney-Nickel / methanol / 6 h / Ambient temperature View Scheme

1-naphthalenecarboxylic acid (86-55-5) → dibenz[a,j]anthracene (224-41-9)

Conditions	Yield
Multi-step reaction with 4 steps 1: SOCl2, dimethyl formamide / benzene / 2 h 2: 18.5 g / diethyl ether / 1 h / 0 °C 3: 1.) TMEDA, triphenylmethyl chloride, sec-BuLi / 1.) ether, cyclohexane, -78 deg C, 1 h, 2.) a) -78 deg, 1 h, b) room temp., 3 h 4: 80 percent / HI, H3PO2 / acetic acid / 240 h / Heating View Scheme

dibenz[a,j]anthracene (224-41-9) + cyclohexa-1,3-diene (1165952-91-9) → C28H22 (80992-42-3) + C28H22 (80992-41-2)

Conditions	Yield
In benzene Irradiation;	A 91% B 9%
In benzene Irradiation;	A 11% B 89%

dibenz[a,j]anthracene (224-41-9) → 7-bromodibenz[a,j]anthracene

Conditions	Yield
With N-Bromosuccinimide; iron(III) chloride In tetrachloromethane Bromination; Heating;	91%

maleic anhydride (108-31-6) + dibenz[a,j]anthracene (224-41-9) → C26H16O3

Conditions	Yield
In various solvent(s) at 91.5℃; Mechanism; Rate constant; analogous reaction of other polycyclic aromatic hydrocarbons; structure/reactivity correlations, application of theoretical models;

dibenz[a,j]anthracene (224-41-9) + acetic acid (64-19-7) + CrO3 → 7.14-dioxo-7.14-dihydro-dibenzanthracene

Upstream product

• 90-12-0 1-Methylnaphthalene 
• 19399-64-5 5,6,8,9-Tetrahydrodibenzoanthracene 
• 1725-76-4 (E,E)-1,3-distyrylbenzene 
• 32277-35-3 1,2-dihydrocyclobuteno[α]naphthalene 
• 130800-12-3 C₂₂H₃₀O₂ 
• 73540-68-8 3-Naphthalen-2-yl-3H-naphtho[1,2-c]furan-1-one 
• 77321-42-7 2-(Naphthalene-2-carbonyl)-naphthalene-1-carboxylic acid 
• 134576-19-5 7-(Methylthio)-dibenzanthracene 
• 81194-74-3 lithium salt of N,N-diethyl-1-naphthtamide 
• 66-99-9 β-naphthaldehyde 
• 89988-22-7 trans-9,10-dihydro-2-styrylphenanthrene 
• 75-15-0 carbon disulfide 
• 7446-70-0 aluminium trichloride 
• 86-52-2 1-Chloromethylnaphthalene 

Downstream Products

• 134273-46-4 3-(2-Formylphenyl)-2-phenanthrenecarboxaldehyde 
• 41774-33-8 Dibenzoanthrachinone 
• 131407-74-4 dibenz[a,j]anthracene-5,6-oxide 
• 52755-66-5 dibenzanthracene-5,6-dione 

Relevant articles and documents

Reductive Cyclization of Keto Acids to Polycyclic Aromatic Hydrocarbons by Hydroiodic Acid-Red Phosphorus

Hydroiodic acid-red phosphorus in acetic acid causes ring closure of o-naphthoylbenzoic acids and of o-naphthoylnaphthoic acids to yield benzanthracene and dibenzanthracenes

A New General Synthesis of Polycyclic Aromatic Compounds Based on Enamine Chemistry

Alkylation of enamines and enamine salts by benzylic and (β-haloethyl)aryl halides, respectively, followed by acidic cyclodehydration and dehydrogenation provides an efficient synthetic approach to a wide range of polycyclic aromatic compounds of diverse structural types.Specific polycyclic hydrocarbons synthesized by this route include benzo- and benzofluorene, 7H-dibenzo-, 13H-dibenzo-, and 13H-dibenzofluorene, 15H-tribenzofluorene, dibenzochrysene, benzopentaphene, indenofluorene, fluorenofluorene, octahydrodibenzanthracene, dibenzanthracene, octahydrodibenzanthracene, dibenzanthracene, picene, benzopicene, 1H-benzaceanthrylene, and 4H-cyclopentachrysene.This method with appropriate modifications appears to be potentially broader in scope than established traditional methods of polycyclic hydrocarbon synthesis.

The Syntheses of 4b,5a-Dihydrodibenzanthraoxirene and 4b,5a-Dihydro-5H-dibenzanthraazirine

The syntheses of the K-oxide and K-imine derivatives of dibenzanthracene (1) are described.The parent hydrocarbon 1 that was obtained as a side product in the Elbs pyrolysis of (2-methyl-1-naphthyl)-1'-naphthylmethanone (10) was oxidized to 3-(2-formylphenyl)-3-phenanthrenecarboxaldehyde (3).Treatment of the dialdehyde with tris(dimethylamino)phosphine gave 4b,5a-dihydrodibenzanthraoxirene (4).Reaction of the oxirane with sodium azide followed by triethyl phosphite cyclization of the mixture of trans azido-alcohols so formed, yielded mainly 4b,5a-dihydrodibenzanthraazirine (5).