Benzo(A)pyrene-6,12-dione

Base Information

• Chemical Name: Benzo(A)pyrene-6,12-dione
• CAS No.: 3067-12-7
• Molecular Formula: C20H10 O2
• Molecular Weight: 282.298
• Hs Code.: 2914399090
• NSC Number: 625589
• UNII: QWW9F0H8TO
• DSSTox Substance ID: DTXSID20952916
• Nikkaji Number: J36.064C
• Wikidata: Q82931635
• ChEMBL ID: CHEMBL1977197
• Mol file: 3067-12-7.mol

Synonyms:benzo(a)pyrene-6,12-dione;benzo(a)pyrene-6,12-quinone;benzo(a)pyrene-7,8-quinone

Chemical Property of Benzo(A)pyrene-6,12-dione

Chemical Property:

• Vapor Pressure: 2.16E-11mmHg at 25°C
• Melting Point: 321°C
• Refractive Index: 1.6440 (estimate)
• Boiling Point: 531.9°C at 760 mmHg
• Flash Point: 195.6°C
• PSA: 34.14000
• Density: 1.42g/cm³
• LogP: 3.84700
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 282.068079557
• Heavy Atom Count: 22
• Complexity: 560

Purity/Quality:

99% ^*data from raw suppliers

Benzo[a]pyrene-6,12-quinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Polycyclic Aromatic Hydrocarbons
• Canonical SMILES: C1=CC=C2C(=C1)C3=CC(=O)C4=CC=CC5=C4C3=C(C2=O)C=C5
• 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.

Technology Process of Benzo(A)pyrene-6,12-dione

There total 28 articles about Benzo(A)pyrene-6,12-dione which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

benzopyrene (50-32-8,42299-33-2,34505-58-3) → benzo[a]pyrene-6,12-dione (3067-12-7,64133-80-8) + benzopyren-6-yl acetate (53555-67-2) + benzo[a]pyrene-1,6-quinone (3067-13-8) + benzo[a]pyrene-3,6-dione (3067-14-9)

Guidance literature:

With manganese triacetate; In acetic acid; at 40 ℃; for 0.5h; Title compound not separated from byproducts;

DOI:10.1021/jo00276a013

Reference yield: 90.0%

benzopyrene (50-32-8,42299-33-2,34505-58-3) + Mangantriacetat → benzo[a]pyrene-6,12-dione (3067-12-7,64133-80-8) + benzopyren-6-yl acetate (53555-67-2) + benzo[a]pyrene-1,6-quinone (3067-13-8) + benzo[a]pyrene-3,6-dione (3067-14-9)

Guidance literature:

In acetic acid; at 40 ℃; for 0.166667h; Product distribution; Mechanism; other 6-, 1,6-, and 3,6-substituted benzopyrenes;

DOI:10.1021/jo00276a013

Reference yield: 31.0%

6-fluorobenzopyrene (59417-86-6) → benzo[a]pyrene-6,12-dione (3067-12-7,64133-80-8) + benzopyren-6-yl acetate (53555-67-2) + benzo[a]pyrene-1,6-quinone (3067-13-8) + benzo[a]pyrene-3,6-dione (3067-14-9)

Guidance literature:

With manganese triacetate; In acetic acid; at 40 ℃; for 0.416667h; Further byproducts given. Title compound not separated from byproducts;

DOI:10.1021/jo00276a013

upstream raw materials:

naphthalene

phthalidyliden-acetic acid

benzopyrene

6-fluorobenzopyrene

Downstream raw materials:

6,12-dimethoxybenzopyrene

Refernces

• 1、 Sorokin, Alexander,Meunier, Bernard. "Oxidation of polycyclic aromatic hydrocarbons catalyzed by iron tetrasulfophthalocyanine FePcS: Inverse isotope effects and oxygen labeling studies". . p. 1269 - 1281. Retrieved 1998.
• 2、 Fukuhara,Kurihara,Miyata. "Photochemical generation of nitric oxide from 6-nitrobenzo[a]pyrene". . p. 8662 - 8666. Retrieved 2007/10/03.
• 3、 Cremonesi, Paolo,Stack, Douglas E.,Rogan, Eleanor G.,Cavalieri, Ercole L.. "Radical Cations of Benzopyrene and 6-Substituted Derivatives: Synthesis and Reaction with Nucleophiles". . p. 7683 - 7687. Retrieved 2007/10/02.