• Name

  DIBENZO(A,J)ANTHRACENE

• EINECS
• CAS No. 224-41-9
• Article Data26
• CAS DataBase
• Density 1.232g/cm³
• Solubility 8.629ug/L(25 oC)
• Melting Point 197.5°C
• Formula C22H14
• Boiling Point 524.7°Cat760mmHg
• Molecular Weight 278.353
• Flash Point 264.5°C
• Transport Information
• Appearance
• Safety Questionable carcinogen with experimental tumorigenic data. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes. See also ANTHRACENE.
• Risk Codes 25-36/37/38-52/53
• Molecular Structure
• Hazard Symbols T
• Synonyms 1,2:7,8-Dibenzanthracene;3,4:5,6-Dibenzanthracene; Dibenzo-1,2,7,8-anthracene; NSC 90321
• PSA 0.00000
• LogP 6.29940

Synthetic route

868847-77-2

2,4',6',2''-tetravinyl-[1,1';3',1'']terphenyl

224-41-9

dibenz[a,j]anthracene

Conditions

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

130799-92-7

1,2,3,4,10,11,12,13-Octahydrodibenzanthracene

224-41-9

dibenz[a,j]anthracene

Conditions

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

81205-71-2

14-acetoxydibenzanthracene

224-41-9

dibenz[a,j]anthracene

Conditions

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

77321-42-7

2-(Naphthalene-2-carbonyl)-naphthalene-1-carboxylic acid

224-41-9

dibenz[a,j]anthracene

Conditions

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

73540-68-8

3-Naphthalen-2-yl-3H-naphtho[1,2-c]furan-1-one

224-41-9

dibenz[a,j]anthracene

Conditions

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

134576-19-5

7-(Methylthio)-dibenzanthracene

224-41-9

dibenz[a,j]anthracene

Conditions

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

1725-76-4

(E,E)-1,3-distyrylbenzene

A

194-69-4

benzo[c]chrysene

B

224-41-9

dibenz[a,j]anthracene

Conditions

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

103224-51-7

7,14-dihydro-14-ethoxy-7-(trimrthylsilyl)-7,14-epoxydibenzanthracene

224-41-9

dibenz[a,j]anthracene

Conditions

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

80992-42-3

C28H22

A

224-41-9

dibenz[a,j]anthracene

82344-75-0

C28H22

80992-41-2

C28H22

Conditions

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;

...Expand

41774-28-1

(2-methylnaphthalen-1-yl)(naphthalen-1-yl)methanone

A

53-70-3

dibenzo[a,h]anthracene

B

224-41-9

dibenz[a,j]anthracene

Conditions

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

90-12-0

1-Methylnaphthalene

A

213-46-7

picene

B

53-70-3

dibenzo[a,h]anthracene

C

214-17-5

Benzo[b]chrysene

D

224-41-9

dibenz[a,j]anthracene

Conditions

Conditions	Yield
at 750℃;

...Expand

19399-64-5

5,6,8,9-Tetrahydrodibenzoanthracene

224-41-9

dibenz[a,j]anthracene

Conditions

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

41774-36-1

14H-dibenz[a,j]anthracen-7-one

224-41-9

dibenz[a,j]anthracene

Conditions

Conditions	Yield
With sodium hydroxide; zinc

32277-35-3

1,2-dihydrocyclobutene[α]naphthalene

A

53-70-3

dibenzo[a,h]anthracene

B

224-41-9

dibenz[a,j]anthracene

Conditions

Conditions	Yield
at 890℃;

130800-12-3

C22H30O2

224-41-9

dibenz[a,j]anthracene

Conditions

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

81194-74-3

lithium salt of N,N-diethyl-1-naphthtamide

66-99-9

β-naphthaldehyde

224-41-9

dibenz[a,j]anthracene

Conditions

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;

89988-22-7

trans-9,10-dihydro-2-styrylphenanthrene

A

194-69-4

benzo[c]chrysene

B

224-41-9

dibenz[a,j]anthracene

Conditions

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;

75-15-0

carbon disulfide

7446-70-0

aluminium trichloride

86-52-2

1-Chloromethylnaphthalene

2506-41-4

1-chloromethylnaphthalene

A

53-70-3

dibenzo[a,h]anthracene

B

226-88-0

benzo[a]naphthacene

C

224-41-9

dibenz[a,j]anthracene

Conditions

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

...Expand

75-15-0

carbon disulfide

7446-70-0

aluminium trichloride

86-52-2

1-Chloromethylnaphthalene

91-57-6

2-Methylnaphthalene

A

53-70-3

dibenzo[a,h]anthracene

B

226-88-0

benzo[a]naphthacene

C

224-41-9

dibenz[a,j]anthracene

Conditions

Conditions	Yield
Erhitzen des Reaktionsprodukts mit Kupfer-Pulver;

...Expand

7-oxo-7.14-dihydro-dibenz<a.j>anthracene

7-oxo-7.14-dihydro-dibenz<a.j>anthracene

224-41-9

dibenz[a,j]anthracene

Conditions

Conditions	Yield
With sodium hydroxide; zinc

dibenz<a.j>anthracene-dicarboxylic acid-(6.8)

dibenz<a.j>anthracene-dicarboxylic acid-(6.8)

224-41-9

dibenz[a,j]anthracene

Conditions

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

868847-74-9

1,5-dibromo-2,4-divinylbenzene

224-41-9

dibenz[a,j]anthracene

Conditions

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

58997-70-9

1,5-dibromo-2,4-bis(dibromomethyl)benzene

224-41-9

dibenz[a,j]anthracene

Conditions

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

615-87-2

1,5-dibromo-2,4-dimethylbenzene

224-41-9

dibenz[a,j]anthracene

Conditions

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

97094-37-6

2,4-dibromobenzene-1,5-dicarboxaldehyde

224-41-9

dibenz[a,j]anthracene

Conditions

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

108-38-3

m-xylene

224-41-9

dibenz[a,j]anthracene

Conditions

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

90-11-9

1-Bromonaphthalene

soda lime

soda lime

224-41-9

dibenz[a,j]anthracene

Conditions

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

134576-15-1

7-(Methylthio)-5,6-dihydrodibenzanthracene

224-41-9

dibenz[a,j]anthracene

Conditions

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

86-55-5

1-naphthalenecarboxylic acid

224-41-9

dibenz[a,j]anthracene

Conditions

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

224-41-9

dibenz[a,j]anthracene

1165952-91-9

cyclohexa-1,3-diene

80992-42-3

C28H22

80992-41-2

C28H22

Conditions

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

...Expand

224-41-9

dibenz[a,j]anthracene

7-bromodibenz[a,j]anthracene

Conditions

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

108-31-6

maleic anhydride

224-41-9

dibenz[a,j]anthracene

C26H16O3

Conditions

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;

224-41-9

dibenz[a,j]anthracene

64-19-7

acetic acid

CrO3

CrO3

7.14-dioxo-7.14-dihydro-dibenz<a.j>anthracene

7.14-dioxo-7.14-dihydro-dibenz<a.j>anthracene

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DIBENZ(a,j)ANTHRACENE Chemical Properties

DIBENZ(a,j)ANTHRACENE Toxicity Data With Reference

DIBENZ(a,j)ANTHRACENE Consensus Reports

DIBENZ(a,j)ANTHRACENE Safety Profile

DIBENZ(a,j)ANTHRACENE Specification