3067-12-7

Basic information

• Product Name: 6,12-Benzo(a)pyrenedione
• Synonyms: 6,12-Benzo(a)pyrenedione;benzo(a)pyrene-6,12-quinone;6,12-BENZO(A)PYRENEQUINONE;6,12-Dihydrobenzo[a]pyrene-6,12-dione;BP-6,12-Q
• CAS NO: 3067-12-7
• Molecular Formula: C₂₀H₁₀O₂
• Molecular Weight: 282.30
• Mol File: 3067-12-7.mol
• Article Data: 7

Chemical Properties

• Melting Point: 321°C
• Boiling Point: 384.91°C (rough estimate)
• Flash Point: 195.6°C
• Appearance: /
• Density: 1.1639 (rough estimate)
• Vapor Pressure: 2.16E-11mmHg at 25°C
• Refractive Index: 1.6440 (estimate)
• CAS DataBase Reference: 6,12-Benzo(a)pyrenedione(CAS DataBase Reference)
• NIST Chemistry Reference: 6,12-Benzo(a)pyrenedione(3067-12-7)
• EPA Substance Registry System: 6,12-Benzo(a)pyrenedione(3067-12-7)

Safety Data

• Hazardous Substances Data: 3067-12-7(Hazardous Substances Data)

Usage

Uses

Benzo[a]pyrene-6,12-quinone is a polycyclic aromatic hydrocarbon (PAH) and metabolite of Benzopyrene (B205800) that can have toxic effects on fish bone metabolism. In utero exposure to Benzo[a]pyrene-6,12-quinone can also predispose offspring to cardiovascular dysfunction in later life.

Synthesis Reference(s)

Journal of the American Chemical Society, 78, p. 446, 1956 DOI: 10.1021/ja01583a053The Journal of Organic Chemistry, 40, p. 3283, 1975 DOI: 10.1021/jo00910a028

Safety Profile

Questionable carcinogen withexperimental neoplastigenic data. Mutation data reported.When heated to decomposition it emits acrid smoke andirritating fumes.

InChI:InChI=1/C20H10O2/c21-17-10-16-12-5-1-2-6-13(12)20(22)15-9-8-11-4-3-7-14(17)18(11)19(15)16/h1-10H

Upstream product

• 91-20-3 naphthalene 
• 4743-57-1 phthalidyliden-acetic acid 
• 50-32-8 benzopyrene 
• 59417-86-6 6-fluorobenzopyrene 
• 21248-01-1 6-Chlorobenzo[a]pyrene 
• 21248-00-0 6-Bromobenzo[a]pyrene 
• 10581-12-1 tetramethyl ammonium acetate 
• 127-09-3 sodium acetate 
• 85-44-9 phthalic anhydride 
• 63041-90-7 6-nitrobenzo(a)pyrene 
• 7664-39-3 hydrogen fluoride 

Downstream Products

• 74192-49-7 6,12-dimethoxybenzopyrene 

Relevant articles and documents

Radical cations of benzo[a]pyrene and 6-substituted derivatives: Reaction with nucleophiles and DNA

1. Oxidation of benzo[a]pyrene (BP) by I2 in the presence of AgClO4 in benzene generates the BP.+ ClO4- · AgI complex. This same method was used to produce radical cations from 6-FBP, 6-ClBP, 6-BrBP and 6-CH3BP. 2. Reaction of the BP,6-FBP,6-ClBP and 6-BrBP radical cation perchlorates with H2O produced BP 1,6-, 3,6- and 6,12- dione, whereas 6-CH3BP.+ClO4- · AgI yielded 6-CH2OHBP. 3. When BP.+ClO4- · AgI and 6-FBP.+ClO4- · AgI were reacted with NaOAc in H2O/CH3CN (9:1), 6-OAcBP was formed, in addition to the quinones. In the case of 6-CIBP.+ClO4- · AgI, a small amount of 1-OAc-6-ClBP and 3-OAc-6-ClBP was formed in, addition to the diones, whereas for 6-BrBP and 6-CH3BP the reaction products were BP diones and 6-CH2OHBP respectively. 4. These results confirm the localization of charge in the BP.+ at C-6, followed by C-1 and C-3. 5. The reaction of BP with NOBF4 in CH2Cl2 produced BP.+ BF4-, radical cation free of complexation with inorganic salts. 6. Reaction of BP.+BF4- with DNA produced the depurinating adducts BP-6-C8Gua, BP-6-C8dGua and BP-6-N7Gua.

Photooxygenation of polycyclic aromatic hydrocarbons by pyrimido[5,4-g]pteridine N-oxide

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