Benzo[a]pyrene-1,6-dione

Base Information

• Chemical Name: Benzo[a]pyrene-1,6-dione
• CAS No.: 3067-13-8
• Molecular Formula: C20H10 O2
• Molecular Weight: 282.298
• Hs Code.: 2914399090
• NSC Number: 30985
• UNII: MS3758O6C7
• DSSTox Substance ID: DTXSID80952917
• Nikkaji Number: J36.062G
• Wikidata: Q26998371
• Mol file: 3067-13-8.mol

Synonyms:benzo(a)pyrene-1,6-quinone;benzo(a)pyrene-1,6-quinone ion (-1)

Chemical Property of Benzo[a]pyrene-1,6-dione

Chemical Property:

• Vapor Pressure: 5.79E-12mmHg at 25°C
• Melting Point: 295°C (rough estimate)
• Refractive Index: 1.6440 (estimate)
• Boiling Point: 545.7°Cat760mmHg
• Flash Point: 200.2°C
• PSA: 34.14000
• Density: 1.426g/cm³
• LogP: 4.26070
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly, Heated)
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 282.068079557
• Heavy Atom Count: 22
• Complexity: 548

Purity/Quality:

99%, ^*data from raw suppliers

Benzo[a]pyrene-1,6-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=C4C(=O)C=CC5=C4C3=C(C2=O)C=C5
• Uses: Benzo[a]pyrene-1,6-quinone is a metabolite of Benzopyrene (B205800) and is able to induce epidermal growth factor receptor (EGFR) cell signaling in human mammary epithelial cells. Also highly mutagenic and carcinogenic.

Technology Process of Benzo[a]pyrene-1,6-dione

There total 25 articles about Benzo[a]pyrene-1,6-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: 57.0%

6-fluorobenzopyrene (59417-86-6) + Mangantriacetat → benzopyren-6-yl acetate (53555-67-2) + 1,6-diacetoxy-benzo[def]chrysene (42499-08-1) + benzo[a]pyrene-1,6-quinone (3067-13-8) + 3,6-diacetoxy-benzo[def]chrysene (42286-47-5)

Guidance literature:

In acetic acid; at 40 ℃; for 0.416667h; Further byproducts given. Yields of byproduct given;

DOI:10.1021/jo00276a013

upstream raw materials:

octane

benzopyrene

6-fluorobenzopyrene

acetone

Downstream raw materials:

1,6-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 2007/10/03.
• 2、 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.