191-30-0

Basic information

• Product Name: DIBENZO(A,I)PYRENE
• Synonyms: DIBENZO(A,L)PYRENE;DIBENZO(A,I)PYRENE;DIBENZ(A,L)PYRENE;DIBENZ(A,I)PYRENE;3,4,9,10-DIBENZOPYRENE;1,2,3,4-DIBENZPYRENE;1,2:7,8-DIBENZPYRENE;1,2,9,10-Dibenzopyrene
• CAS NO: 191-30-0
• Molecular Formula: C₂₄H₁₄
• Molecular Weight: 302.37
• EINECS: 205-886-4
• Product Categories: Alpha Sort;D;DAlphabetic;DIA - DIC;Volatiles/ Semivolatiles;Aromatics;Metabolites & Impurities;Mutagenesis Research Chemicals
• Mol File: 191-30-0.mol
• Article Data: 3

Chemical Properties

• Melting Point: 228.05°C
• Boiling Point: 378.4°C (rough estimate)
• Flash Point: 349.8°C
• Appearance: /
• Density: 1.1762 (estimate)
• Vapor Pressure: 3.99E-15mmHg at 25°C
• Refractive Index: 1.9130 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Very Slightly, Heated), Dichloromethane (Slightly, Heated)
• Stability: Stable, but may be heat sensitive - keep cool. Combustible. Incompatible with strong oxidizing agents.
• BRN: 2054068
• CAS DataBase Reference: DIBENZO(A,I)PYRENE(CAS DataBase Reference)
• NIST Chemistry Reference: DIBENZO(A,I)PYRENE(191-30-0)
• EPA Substance Registry System: DIBENZO(A,I)PYRENE(191-30-0)

Safety Data

• Hazard Codes: Xn,T
• Statements: 40-67-36/37/38-45-41-52/53
• Safety Statements: 23-24/25-36/37-45-26-53-39-61
• RIDADR: 2811
• WGK Germany: 3
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 191-30-0(Hazardous Substances Data)

Usage

Chemical Properties

Yellow Solid

Uses

An active metabolite from inhalation and dermal exposure to polycyclic aromatics hydrocarbons in hot mix asphalt paving workers. DBC is the most potent tumorigen that has been identified to date. Dib enzo[def,p]chrysene (DBC) is a carcinogen and should be handled with appropriate caution.

Air & Water Reactions

Dust/air mixtures may ignite and explode. Insoluble in water.

Safety Profile

Confirmed carcinogen with experimental tumorigenic data. When heated to decomposition it emits acrid smoke and irritating fumes.

Carcinogenicity

Dibenzo[a,1]pyrene is a class 2B carcinogen according to the IARC, although recent data suggest that it is a 2A carcinogen. In mouse studies, it has been more potent than benzo[a]pyrene in skin, and in rat studies, it has been more potent than 7,12-dimethylbenz [a]anthracene in the mammary gland. Dibenzo[a,l]pyrene was tested for carcinogenicity in studies of single and repeated dermal application to mice, as well as several initiation–promotion studies on mouse skin; all studies gave positive results. Dibenzo[a,l] pyrene also induced oral cavity tumors when applied dermally to the tongue of hamsters and lung tumors in mice following intraperitoneal injection. In addition to lung tumors, dibenzo[a,l]pyrene induced hepatic tumors and a variety of tumors at other sites when administered intraperitoneally to newborn mice. Multiple tumor sites were also observed following intragastric application of dibenzo[a,l]pyrene in mice. Intramamillary administration to rats also yielded positive results. Furthermore, two studies on fish demonstrated that nonmammalian species are also susceptible to dibenzo[a,l]pyreneinduced tumorigenicity.The most active metabolite is the potent 11,12-dihydrodiol of dibenzo[a,1] pyrene.

InChI:InChI=1/C24H16/c1-2-8-18-16(6-1)14-17-13-12-15-7-5-11-20-19-9-3-4-10-21(19)24(18)23(17)22(15)20/h1-16H

Synthetic route

N-[2-(5,6-dihydro-4H-benz[de]anthracen-7-yl)benzylidene]aniline → Dibenzo[a,l]pyrene (191-30-0)

Conditions	Yield
Stage #1: N-[2-(5,6-dihydro-4H-benz[de]anthracen-7-yl)benzylidene]aniline With potassium hydroxide In N,N-dimethyl-formamide at 100℃; for 1h; Stage #2: With 2,3-dicyano-5,6-dichloro-p-benzoquinone In benzene for 0.5h; Heating;	88%

9-(2-methoxy-vinyl)-benzo[g]chrysene (1013933-57-7) → Dibenzo[a,l]pyrene (191-30-0)

Conditions	Yield
With methanesulfonic acid In dichloromethane at 20℃; for 2.5h;	75%

Pentahelicen-3-carbonsaeure-methylester (13322-54-8) → Dibenzo[a,l]pyrene (191-30-0)

Conditions	Yield
ueber Dibenzo<def,p>chrysen-8-ol;

benz[a]anthracene (56-55-3) + benzene (71-43-2) → Dibenzo[a,l]pyrene (191-30-0)

Conditions	Yield
With aluminium trichloride; ortho-toluoyl chloride

1-Phenylbenzanthracen (10383-87-6) → Dibenzo[a,l]pyrene (191-30-0)

Conditions	Yield
With aluminium trichloride; tin(IV) chloride

C24H14O (17181-10-1) → Dibenzo[a,l]pyrene (191-30-0)

Conditions	Yield
With sodium chloride; zinc(II) chloride; zinc

12-phenyl-benz[a]anthracene (7424-73-9) → Dibenzo[a,l]pyrene (191-30-0)

Conditions	Yield
With aluminium trichloride

1,10-trimethylenephenanthrene (4389-09-7) → Dibenzo[a,l]pyrene (191-30-0)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: 86 percent / Br2 / CCl4 / 2 h / Heating 2.1: 61 percent / CsF / Pd(PPh3)4 / dimethylformamide / 24 h 3.1: 96 percent / molecular sieves 4 Angstroem / CH2Cl2 / 4 h 4.1: KOH / dimethylformamide / 1 h / 100 °C 4.2: 88 percent / DDQ / benzene / 0.5 h / Heating View Scheme

7-bromo-5,6-dihydro-4H-benz[de]anthracene (681215-15-6) → Dibenzo[a,l]pyrene (191-30-0)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 61 percent / CsF / Pd(PPh3)4 / dimethylformamide / 24 h 2.1: 96 percent / molecular sieves 4 Angstroem / CH2Cl2 / 4 h 3.1: KOH / dimethylformamide / 1 h / 100 °C 3.2: 88 percent / DDQ / benzene / 0.5 h / Heating View Scheme

7-(2-formylphenyl)-5,6-dihydro-4H-benz[de]anthracene (681215-16-7) → Dibenzo[a,l]pyrene (191-30-0)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 96 percent / molecular sieves 4 Angstroem / CH2Cl2 / 4 h 2.1: KOH / dimethylformamide / 1 h / 100 °C 2.2: 88 percent / DDQ / benzene / 0.5 h / Heating View Scheme

1-Phenyl-3,4-dihydro-benzo[a]anthracene (29568-49-8) → Dibenzo[a,l]pyrene (191-30-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: DDQ 2: AlCl3, SnCl4 View Scheme

phenylmagnesium bromide + biacetyl monooxime → Dibenzo[a,l]pyrene (191-30-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: (i), (ii) (heating) 2: DDQ 3: AlCl3, SnCl4 View Scheme

Dibenzo[a,l]pyrene (191-30-0) + Mangantriacetat → C26H16O2 (141396-61-4)

Conditions	Yield
In acetic acid; benzene at 40℃; for 4h;	86%
In acetic acid; benzene at 40℃; Rate constant; Mechanism;

Dibenzo[a,l]pyrene (191-30-0) → dibenzo[a,l]pyrene-8,9-quinone (226420-31-1)

Conditions	Yield
With sodium periodate; rhodium(III) chloride hydrate In dichloromethane; water; acetonitrile at 30 - 40℃;	58%
Multi-step reaction with 2 steps 1.1: OsO4 / pyridine / 144 h / 20 °C 1.2: NaHSO4 / 1 h / 20 °C 2.1: 2,3-dichloro-5,6-dicyano-p-benzoquinone / dioxane / 168 h / under argon atmosphere View Scheme
Multi-step reaction with 2 steps 1: OsO4 / pyridine / 168 h / 25 °C 2: DDQ / dioxane / 15 h / Heating View Scheme

Dibenzo[a,l]pyrene (191-30-0) + adenine (66224-66-6, 66224-67-7, 66224-68-8, 66224-69-9, 134434-48-3, 134434-49-4, 134454-76-5, 134461-75-9) → C29H17N5 + C29H17N5 + C29H17N5 + C29H17N5

Conditions	Yield
With potassium perchlorate In N,N-dimethyl-formamide for 2h; Electrochemical reaction;	A 2% B 5% C 47% D 6%
With potassium perchlorate In dimethyl sulfoxide for 2h; Electrochemical reaction;	A 1% B 9% C 44% D 3%

Dibenzo[a,l]pyrene (191-30-0) + 2'-deoxy-D-adenosine (958-09-8) → C29H17N5 + C29H17N5 + C34H25N5O3

Conditions	Yield
With potassium perchlorate In N,N-dimethyl-formamide for 2h; Electrochemical reaction;	A 3% B 25% C 26%

2-amino-1,9-dihydro-6H-purin-6-one (73-40-5) + Dibenzo[a,l]pyrene (191-30-0) → C29H17N5O + 8-(10-dibenzo[def,p]chrysenyl)guanine

Conditions	Yield
With iodine; silver perchlorate In dimethyl sulfoxide Product distribution; Further Variations:; Reagents; Solvents; Iodine oxidation; nucleophilic substitution;	A 23 % Chromat. B 8 % Chromat.

Dibenzo[a,l]pyrene (191-30-0) + 2'-Deoxyguanosine (961-07-9) → C29H17N5O

Conditions	Yield
With iodine; silver perchlorate In N,N-dimethyl-formamide Product distribution; Further Variations:; Reagents; Solvents; Iodine oxidation; nucleophilic substitution;	43 % Chromat.

Dibenzo[a,l]pyrene (191-30-0) + adenine (66224-66-6, 66224-67-7, 66224-68-8, 66224-69-9, 134434-48-3, 134434-49-4, 134454-76-5, 134461-75-9) → C29H17N5 + C29H17N5 + C29H17N5

Conditions	Yield
With iodine; silver perchlorate In N,N-dimethyl-formamide Product distribution; Further Variations:; Reagents; Solvents; Iodine oxidation; nucleophilic substitution;	A 1 % Chromat. B 10 % Chromat. C 47 % Chromat.

Dibenzo[a,l]pyrene (191-30-0) + 2'-deoxy-D-adenosine (958-09-8) → C29H17N5

Conditions	Yield
With iodine; silver perchlorate In N,N-dimethyl-formamide Product distribution; Further Variations:; Reagents; Solvents; Iodine oxidation; nucleophilic substitution;	30 % Chromat.

Dibenzo[a,l]pyrene (191-30-0) → cis-8,9-dihydroxy-8,9-dihydro-dibenzo[a,l]pyrene

Conditions	Yield
With osmium(VIII) oxide In pyridine at 25℃; for 168h;

Dibenzo[a,l]pyrene (191-30-0) → cis-dibenzo[a,l]pyrene-8,9-diol

Conditions	Yield
Stage #1: Dibenzo[a,l]pyrene With osmium(VIII) oxide In pyridine at 20℃; for 144h; Stage #2: With sodium hydrogen sulfate at 20℃; for 1h;

Dibenzo[a,l]pyrene (191-30-0) + N-methyl-N-phenylformamide (93-61-8) → dibenzo[def,p]chrysene-10-carboxaldehyde (2869-59-2)

Conditions	Yield
With trichlorophosphate In 1,2-dichloro-benzene at 90℃; for 8h; Vilsmeier-Haack formylation;

Dibenzo[a,l]pyrene (191-30-0) → (+/-)-trans-8,9-dihydroxy-8,9-dihydro-dibenzo[a,l]pyrene

Conditions	Yield
Multi-step reaction with 3 steps 1.1: OsO4 / pyridine / 144 h / 20 °C 1.2: NaHSO4 / 1 h / 20 °C 2.1: 2,3-dichloro-5,6-dicyano-p-benzoquinone / dioxane / 168 h / under argon atmosphere 3.1: 95 percent / NaBH4; O2 / ethanol; H2O / 72 h View Scheme
Multi-step reaction with 3 steps 1: OsO4 / pyridine / 168 h / 25 °C 2: DDQ / dioxane / 15 h / Heating 3: 36 percent / NaBH4; air / propan-2-ol / 24 h View Scheme

Dibenzo[a,l]pyrene (191-30-0) → (-)-trans-dibenzo[a,l]pyrene-8,9-diol

Conditions	Yield
Multi-step reaction with 5 steps 1.1: OsO4 / pyridine / 144 h / 20 °C 1.2: NaHSO4 / 1 h / 20 °C 2.1: 2,3-dichloro-5,6-dicyano-p-benzoquinone / dioxane / 168 h / under argon atmosphere 3.1: 95 percent / NaBH4; O2 / ethanol; H2O / 72 h 4.1: 31 percent / pyridine / 24 h / 4 °C / under argon 5.1: 56 percent / sodium methoxide / tetrahydrofuran; methanol / 4 h / 20 °C View Scheme

Dibenzo[a,l]pyrene (191-30-0) → (+)-trans-dibenzo[a,l]pyrene-8,9-diol

Conditions	Yield
Multi-step reaction with 5 steps 1.1: OsO4 / pyridine / 144 h / 20 °C 1.2: NaHSO4 / 1 h / 20 °C 2.1: 2,3-dichloro-5,6-dicyano-p-benzoquinone / dioxane / 168 h / under argon atmosphere 3.1: 95 percent / NaBH4; O2 / ethanol; H2O / 72 h 4.1: 38 percent / pyridine / 24 h / 4 °C / under argon 5.1: 29 percent / sodium methoxide / tetrahydrofuran; methanol / 4 h / 20 °C View Scheme

Dibenzo[a,l]pyrene (191-30-0) → (+)-trans-(8S,9S)-bis-[(-)-menthoxyacetoxy]-8,9-dihydrodibenzo[a,l]pyrene

Conditions	Yield
Multi-step reaction with 4 steps 1.1: OsO4 / pyridine / 144 h / 20 °C 1.2: NaHSO4 / 1 h / 20 °C 2.1: 2,3-dichloro-5,6-dicyano-p-benzoquinone / dioxane / 168 h / under argon atmosphere 3.1: 95 percent / NaBH4; O2 / ethanol; H2O / 72 h 4.1: 31 percent / pyridine / 24 h / 4 °C / under argon View Scheme

Dibenzo[a,l]pyrene (191-30-0) → (-)-trans-(8R,9R)-bis-[(-)-menthoxyacetoxy]-8,9-dihydrodibenzo[a,l]pyrene

Conditions	Yield
Multi-step reaction with 4 steps 1.1: OsO4 / pyridine / 144 h / 20 °C 1.2: NaHSO4 / 1 h / 20 °C 2.1: 2,3-dichloro-5,6-dicyano-p-benzoquinone / dioxane / 168 h / under argon atmosphere 3.1: 95 percent / NaBH4; O2 / ethanol; H2O / 72 h 4.1: 38 percent / pyridine / 24 h / 4 °C / under argon View Scheme

Dibenzo[a,l]pyrene (191-30-0) → (+)-trans-8,9-dihydroxy-8,9-dihydro-dibenzo[a,l]pyrene

Conditions	Yield
Multi-step reaction with 4 steps 1: OsO4 / pyridine / 168 h / 25 °C 2: DDQ / dioxane / 15 h / Heating 3: 36 percent / NaBH4; air / propan-2-ol / 24 h 4: tetrahydrofuran / (R,R)-Whelk-O15 chiral stationary phase column View Scheme

Dibenzo[a,l]pyrene (191-30-0) → (-)-trans-8,9-dihydroxy-8,9-dihydro-dibenzo[a,l]pyrene

Conditions	Yield
Multi-step reaction with 4 steps 1: OsO4 / pyridine / 168 h / 25 °C 2: DDQ / dioxane / 15 h / Heating 3: 36 percent / NaBH4; air / propan-2-ol / 24 h 4: tetrahydrofuran / (R,R)-Whelk-O15 chiral stationary phase column View Scheme

Upstream product

• 1013933-57-7 9-(2-methoxy-vinyl)-benzo[g]chrysene 
• 29568-49-8 1-Phenyl-3,4-dihydro-benzo[a]anthracene 
• 681215-16-7 7-(2-formylphenyl)-5,6-dihydro-4H-benz[de]anthracene 
• 681215-15-6 7-bromo-5,6-dihydro-4H-benz[de]anthracene 
• 4389-09-7 1,10-trimethylenephenanthrene 
• 7424-73-9 12-phenyl-benz[a]anthracene 
• 17181-10-1 C₂₄H₁₄O 
• 10383-87-6 1-Phenylbenzanthracen 
• 56-55-3 benz[a]anthracene 
• 71-43-2 benzene 
• 13322-54-8 Pentahelicen-3-carbonsaeure-methylester 

Downstream Products

• 2869-59-2 10-Formyl-dibenzopyren 

Relevant articles and documents

A highly abbreviated synthesis of dibenzo[def,p]chrysene and its 12-methoxy derivative, a key precursor for the synthesis of the proximate and ultimate carcinogens of dibenzo[def,p]chrysene

Dibenzo[def,p]chrysene (DBC) (1), is by far the most mutagenic and toxic polycyclic aromatic hydrocarbon identified. Its metabolic activation leads to trans-11,12-dihydroxy-11,12-dihydro-DBC (2), which is further metabolized to the ultimate metabolite, anti-trans-11,12-dihydroxy-13,14-epoxy-11,12,13,14-tetrahydro-DBC (3), that binds to DNA causing mutations and ultimately tumor induction. We report a facile route for the syntheses of DBC (1) and its 12-methoxy derivative (12-methoxy-DBC) (13), a key intermediate for the synthesis of 2 and 3, using a Suzuki cross-coupling approach.