Benzo[a]pyrene-7,8-dione

Base Information

• Chemical Name: Benzo[a]pyrene-7,8-dione
• CAS No.: 65199-11-3
• Molecular Formula: C20H10 O2
• Molecular Weight: 282.29
• Hs Code.: 2914399090
• UNII: 8V4WNR6N7H
• DSSTox Substance ID: DTXSID50215501
• Nikkaji Number: J315.273A
• Wikidata: Q27159898
• Mol file: 65199-11-3.mol

Synonyms:benzo(a)pyrene-7,8-dione;benzopyrene-7,8-dione

Chemical Property of Benzo[a]pyrene-7,8-dione

Chemical Property:

• Vapor Pressure: 3.44E-11mmHg at 25°C
• Boiling Point: 526.9°C at 760 mmHg
• Flash Point: 231.5°C
• PSA: 34.14000
• Density: 1.446g/cm³
• LogP: 4.36260
• XLogP3: 4.6
• 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:

> 95% ^*data from raw suppliers

Benzo[a]?pyrene-?7,8-dione ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C3C(=C1)C=CC4=C3C(=CC5=C4C=CC(=O)C5=O)C=C2
• Uses: Benzo[a]?pyrene-?7,8-dione is a metabolite of Benzopyrene (B205800). Benzopyrene is a known carcinogen.

Technology Process of Benzo[a]pyrene-7,8-dione

There total 19 articles about Benzo[a]pyrene-7,8-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: 92.2%

7-hydroxy benzopyrene (13345-26-1) → benzo[a]pyren-7,8-dione (65199-11-3)

Guidance literature:

With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In N,N-dimethyl-formamide; at 20 ℃; for 1h;

DOI:10.1021/jo030348n

Reference yield: 65.0%

cis-7,8-dihydroxy-7,8,9,10-tetrahydrobenzopyrene (17550-74-2,64314-00-7,59963-01-8) → benzo[a]pyren-7,8-dione (65199-11-3)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,4-dioxane; for 24h; Heating;

DOI:10.1016/S0040-4039(00)86775-1

Reference yield:

benzopyrene (50-32-8,42299-33-2,34505-58-3) → benzo[a]pyren-7,8-dione (65199-11-3) + 7,8-Dihydroxybenzo[a]pyrene (57303-99-8) + 9,10-Dihydroxybenzo[a]pyrene + 4,5-dihydroxybenzo[a]pyrene (57304-00-4)

Guidance literature:

With HepG₂ cells; tris hydrochloride; dimethyl sulfoxide; magnesium chloride; In water; for 72h; Further Variations:; Reagents; Product distribution;

DOI:10.1271/bbb.65.2205

upstream raw materials:

7-hydroxy benzopyrene

cis-7,8-dihydroxy-7,8,9,10-tetrahydrobenzopyrene

benzopyrene

3-methoxybenzopyrene

Downstream raw materials:

(+/-)-r-7,t-8-Dihydroxy-t-9,10-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene

8-hydroxy-benzo[a]pyrene-7-O-sulfate

C₂₀H₁₂O₅S

C₂₁H₁₄O₂

Refernces

• 1、 Wu, Anhui,Duan, Yazhen,Xu, Daiwang,Penning, Trevor M.,Harvey, Ronald G.. "Regiospecific oxidation of polycyclic aromatic phenols to quinones by hypervalent iodine reagents". experimental part. p. 2111 - 2118. Retrieved 2010/04/26.
• 2、 Chun,Kim,Choi. "Modulation of cytochrome P4501-mediated bioactivation of benzo[a]pyrene by volatile allyl sulfides in human hepatoma cells.". . p. 2205 - 2212. Retrieved 2007/10/03.