192-65-4

Basic information

• Product Name: Dibenzo[a,e]pyrene
• Synonyms: 1,2:4,5-Dibenzopyrene;Dibenzo[3,4:6,7]pyrene
• CAS NO: 192-65-4
• Molecular Formula: C₂₄H₁₄
• Molecular Weight: 302.38
• EINECS: 205-891-1
• Mol File: 192-65-4.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 552.265 °C at 760 mmHg
• Flash Point: 281.957 °C
• Appearance: Yellow crystals
• Density: 1.313 g/cm³
• Vapor Pressure: 1.12E-11mmHg at 25°C
• Refractive Index: 1.912
• CAS DataBase Reference: Dibenzo[a,e]pyrene(CAS DataBase Reference)
• NIST Chemistry Reference: Dibenzo[a,e]pyrene(192-65-4)
• EPA Substance Registry System: Dibenzo[a,e]pyrene(192-65-4)

Safety Data

• Hazardous Substances Data: 192-65-4(Hazardous Substances Data)

Usage

General Description

Dibenzo[a,e]pyrene is a polycyclic aromatic hydrocarbon (PAH) that is formed during the incomplete combustion of organic materials, such as tobacco smoke, vehicle exhaust, and industrial processes. It is known to be a potent environmental carcinogen and is classified as a Group 2A carcinogen by the International Agency for Research on Cancer (IARC). Dibenzo[a,e]pyrene has been shown to induce DNA damage, cell transformation, and tumor formation in animal studies. Human exposure to dibenzo[a,e]pyrene occurs primarily through inhalation of polluted air, with potential sources also including contaminated food and water. As such, efforts to minimize human exposure to dibenzo[a,e]pyrene are important for reducing the risk of cancer and other adverse health effects.

InChI:InChI=1/C24H14/c1-2-8-17-16(6-1)14-22-19-10-4-3-9-18(19)20-11-5-7-15-12-13-21(17)24(22)23(15)20/h1-14H

Synthetic route

maleic anhydride (108-31-6) + 8H-dibenz[a,de]anthracene (198-29-8) → Dibenzo[a,e]pyrene (192-65-4)

Conditions	Yield
With xylene anschliessende Behandlung mit wss. NaOH und Erhitzen des Reaktionsprodukts mit ZnCl2 und NaCl auf 290grad;

chrysene (218-01-9) → Dibenzo[a,e]pyrene (192-65-4)

Conditions	Yield
With aluminium trichloride; benzene at 60℃;
With aluminium trichloride; benzene at 60℃;

6-o-tolyl-benz[de]anthracen-7-one → Dibenzo[a,e]pyrene (192-65-4)

Conditions	Yield
at 400 - 410℃;

aluminium trichloride (7446-70-0) + chrysene (218-01-9) + benzene (71-43-2) → Dibenzo[a,e]pyrene (192-65-4)

bituminous housecoal → Dibenzo[a,e]pyrene (192-65-4)

Conditions	Yield
With air Formation of xenobiotics; Heating;

seasoned hardwood → Dibenzo[a,e]pyrene (192-65-4)

Conditions	Yield
With air Formation of xenobiotics; Heating;

Dibenzo[a,e]pyrene (192-65-4) → C24H13Br

Conditions	Yield
With N-Bromosuccinimide In dichloromethane; acetonitrile at 20℃; for 24h;	70.4%

Dibenzo[a,e]pyrene (192-65-4) → 8-Nitronaphtho<1,2,3,4-def>chrysene (99808-66-9)

Conditions	Yield
With nitric acid In acetic anhydride Ambient temperature;	40%

Dibenzo[a,e]pyrene (192-65-4) + Mangantriacetat → 8,14-diacetoxy-naphtho[1,2,3,4-def]chrysene (141396-62-5) + Acetic acid naphtho[1,2,3,4-def]chrysen-8-yl ester (141396-58-9)

Conditions	Yield
In acetic acid; benzene at 40℃; for 7h;	A 8% B 27%
In acetic acid; benzene at 40℃; Rate constant;

Dibenzo[a,e]pyrene (192-65-4) → 8,8'-Bi-naphtho<1,2,3,4-def>chrysenyl (99808-65-8)

Conditions	Yield
In chlorobenzene for 94h; Irradiation;	4.4%

maleic anhydride (108-31-6) + Dibenzo[a,e]pyrene (192-65-4) → benzo[a]coronene-3,4,7,8-tetracarboxylic acid-3,4;7,8-dianhydride (6541-71-5)

Conditions	Yield
With chloranil

Dibenzo[a,e]pyrene (192-65-4) → naphtho[1,2,3,4-def]chrysene-8,14-dione (859745-59-8) + 9,14-dioxo-9,14-dihydro-benzo[b]triphenylene-1-carboxylic acid (643017-35-0)

Conditions	Yield
With sodium dichromate; acetic acid; nitrobenzene
With sodium dichromate; acetic acid

succinic acid anhydride (108-30-5) + Dibenzo[a,e]pyrene (192-65-4) → β-<1,2;4,5-Dibenzo-pyren-8-oyl>-propionsaeure (2476-78-0)

Conditions	Yield
With aluminium trichloride In 1,2-dichloro-benzene

Dibenzo[a,e]pyrene (192-65-4) → 8-Brom-1,2;4,5-dibenzo-pyren (1987-98-0)

Conditions	Yield
With bromine; 1,2,3-trichlorobenzene

Dibenzo[a,e]pyrene (192-65-4) + ortho-toluoyl chloride (933-88-0) → 8-(o-Toluyl)-1,2;4,5-dibenzo-pyren (2950-29-0)

Conditions	Yield
With aluminium trichloride In benzene

Dibenzo[a,e]pyrene (192-65-4) + acetyl chloride (75-36-5) → 8-Acetyl-1,2;4,5-dibenzo-pyren

Conditions	Yield
With aluminium trichloride In dichloromethane

maleic anhydride (108-31-6) + Dibenzo[a,e]pyrene (192-65-4) → Naphtho<1,2,3,4-ghi>perylen-5,6-dicarbonsaeureanhydrid (104488-30-4) + benzo[a]coronene-3,4,7,8-tetracarboxylic acid-3,4;7,8-dianhydride (6541-71-5)

Conditions	Yield
With chloranil for 4h; Heating;	A 3 mg B n/a

maleic anhydride (108-31-6) + Dibenzo[a,e]pyrene (192-65-4) → Naphtho<1,2,3,4-ghi>perylen-5,6-dicarbonsaeureanhydrid (104488-30-4) + C28H12O3 + benzo[a]coronene-3,4,7,8-tetracarboxylic acid-3,4;7,8-dianhydride (6541-71-5)

Conditions	Yield
In chlorobenzene for 70h; Ambient temperature; Irradiation;

4-Phenyl-1,2,4-triazolidine-3,5-dione (4233-33-4) + Dibenzo[a,e]pyrene (192-65-4) → 1-naphtho[1,2,3,4-def]chrysen-8-yl-4-phenyl-[1,2,4]triazolidine-3,5-dione (55425-09-7) + N-Phenylbenzochryseno<4,5,6-ghij>phthalazine-5,6-dicarboximide (114676-02-7) + 1,2-bis(8-naphtho<1,2,3,4-def>chrysenyl)-4-phenyl-1,2,4-triazolidine-3,5-dione

Conditions	Yield
In dichloromethane for 44h; Ambient temperature;	A 21 % Turnov. B 19 mg C 57 mg

4-Phenyl-1,2,4-triazolidine-3,5-dione (4233-33-4) + Dibenzo[a,e]pyrene (192-65-4) → N,N'-(7,8-naphtho<1,2,3,4-def>chrysendiyl)urea (114676-03-8)

Conditions	Yield
In dichloromethane for 0.166667h; Irradiation;	19 % Turnov.

Dibenzo[a,e]pyrene (192-65-4) + 1-naphtho[1,2,3,4-def]chrysen-8-yl-4-phenyl-[1,2,4]triazolidine-3,5-dione (55425-09-7) → N-Phenylbenzochryseno<4,5,6-ghij>phthalazine-5,6-dicarboximide (114676-02-7) + 1,2-bis(8-naphtho<1,2,3,4-def>chrysenyl)-4-phenyl-1,2,4-triazolidine-3,5-dione

Conditions	Yield
With pyridine; bromine In dichloromethane at 8℃; for 144h;	A 0.4 mg B 7.6 mg

Dibenzo[a,e]pyrene (192-65-4) + acetic acid (64-19-7) + Na2Cr2O7 → 9.14-dioxo-9.14-dihydro-dibenzanthracene-carboxylic acid-(1) + 8.14-dioxo-8.14-dihydro-naphtho<1.2.3.4-def>chrysene

Dibenzo[a,e]pyrene (192-65-4) → acetylene (74-86-2) + H2

Conditions	Yield
examination of high-temperature stabiliti; determination of equilibrium concentration; from 1500 to 3000 K;

Dibenzo[a,e]pyrene (192-65-4) → 9,14-dioxo-9,14-dihydro-benzo[b]triphenylene-1-carboxylic acid (643017-35-0) + 8.14-dioxo-8.14-dihydro-naphtho<1.2.3.4-def>chrysene

Conditions	Yield
With sodium dichromate; acetic acid

Dibenzo[a,e]pyrene (192-65-4) → N,N'-(7,8-naphtho<1,2,3,4-def>chrysendiyl)urea (114676-03-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: 21 percent Turnov. / CH2Cl2 / 44 h / Ambient temperature 2: 2.8 mg / Br2, pyridine / CH2Cl2 / 96 h / 8 °C 3: 1 mg / toluene / 3.5 h / Irradiation View Scheme
Multi-step reaction with 2 steps 1: 19 mg / CH2Cl2 / 44 h / Ambient temperature 2: 1 mg / toluene / 3.5 h / Irradiation View Scheme

Dibenzo[a,e]pyrene (192-65-4) → N-Phenylbenzochryseno<4,5,6-ghij>phthalazine-5,6-dicarboximide (114676-02-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 21 percent Turnov. / CH2Cl2 / 44 h / Ambient temperature 2: 2.8 mg / Br2, pyridine / CH2Cl2 / 96 h / 8 °C View Scheme

Dibenzo[a,e]pyrene (192-65-4) → 1,2-bis(8-naphtho<1,2,3,4-def>chrysenyl)-4-phenyl-1,2,4-triazolidine-3,5-dione

Conditions	Yield
Multi-step reaction with 2 steps 1: 21 percent Turnov. / CH2Cl2 / 44 h / Ambient temperature 2: 7.6 mg / Br2, pyridine / CH2Cl2 / 144 h / 8 °C View Scheme

Dibenzo[a,e]pyrene (192-65-4) → 1.2,4.5,8.9-tribenzopyrene (192-47-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: AlCl3 / 1,2-dichloro-benzene 2: N2H4*H2O, NaOH / bis-(2-hydroxy-ethyl) ether / Heating 3: ZnCl2, NaCl / 300 °C View Scheme

Upstream product

• 218-01-9 chrysene 
• 7446-70-0 aluminium trichloride 
• 71-43-2 benzene 
• 108-31-6 maleic anhydride 
• 198-29-8 8H-dibenz[a,de]anthracene 

Downstream Products

• 2950-29-0 8-(o-Toluyl)-1,2;4,5-dibenzo-pyren 
• 192-47-2 1.2,4.5,8.9-tribenzopyrene 
• 114676-02-7 N-Phenylbenzochryseno<4,5,6-ghij>phthalazine-5,6-dicarboximide 
• 74-86-2 acetylene 
• 55425-09-7 1-naphtho[1,2,3,4-def]chrysen-8-yl-4-phenyl-[1,2,4]triazolidine-3,5-dione 

Relevant articles and documents

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Emission factors and importance of PCDD/Fs, PCBs, PCNs, PAHs and PM 10 from the domestic burning of coal and wood in the U.K.

This paper presents emission factors (EFs) derived for a range of persistent organic pollutants (POPs) when coal and wood were subject to controlled burning experiments, designed to simulate domestic burning for space heating. A wide range of POPs were emitted, with emissions from coal being higher than those from wood. Highest EFs were obtained for particulate matter, PM10, (～ 10 g/kg fuel) and polycyclic aromatic hydrocarbons (～ 100 mg/ kg fuel for ΣPAHs). For chlorinated compounds, EFs were highest for polychlorinated biphenyls (PCBs), with polychlorinated naphthalenes (PCNs), dibenzo-p-dioxins (PCDDs) and dibenzofurans (PCDFs) being less abundant. EFs were on the order of 1000 ng/kg fuel for ΣPCBs, 100s ng/ kg fuel for ΣPCNs and 100 ng/kg fuel for ΣPCDD/Fs. The study confirmed that mono- to trichlorinated dibenzofurans, Cl1,2,3DFs, were strong indicators of low temperature combustion processes, such as the domestic burning of coal and wood. It is concluded that numerous PCB and PCN congeners are routinely formed during the combustion of solid fuels. However, their combined emissions from the domestic burning of coal and wood would contribute only a few percent to annual U.K. emission estimates. Emissions of PAHs and PM 10 were major contributors to U.K. national emission inventories. Major emissions were found from the domestic burning for Cl1,2,3DFs, while the contribution of PCDD/F-ΣTEQ to total U.K. emissions was minor.