Benzo[a]pyrene-4,5-oxide

Base Information

• Chemical Name: Benzo[a]pyrene-4,5-oxide
• CAS No.: 37574-47-3
• Molecular Formula: C₂₀H₁₂O
• Molecular Weight: 268.315
• DSSTox Substance ID: DTXSID70958640
• Nikkaji Number: J9.301G
• Wikidata: Q27116150
• Mol file: 37574-47-3.mol

Synonyms:3b,4a-dihydrobenzo(1,2)pyreno(4,5-b)oxirene;4,5-dihydro-4,5-epoxybenzo(a)pyrene;benzo(a)pyrene 4,5-epoxide;benzo(a)pyrene 4,5-epoxide, (+-)-isomer;benzo(a)pyrene 4,5-oxide

Chemical Property of Benzo[a]pyrene-4,5-oxide

Chemical Property:

• Vapor Pressure: 2.37E-10mmHg at 25°C
• Refractive Index: 1.6220 (estimate)
• Boiling Point: 518.9°Cat760mmHg
• Flash Point: 249°C
• Density: 1.39g/cm³
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 268.088815002
• Heavy Atom Count: 21
• Complexity: 445

Purity/Quality:

99% ^*data from raw 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=C2C3=C4C(=CC2=C1)C5C(O5)C6=CC=CC(=C64)C=C3

Technology Process of Benzo[a]pyrene-4,5-oxide

There total 4 articles about Benzo[a]pyrene-4,5-oxide 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: 5.0%

benzopyrene (50-32-8,42299-33-2,34505-58-3) → 4,5-dihydro(epoxy) benzopyrene (37574-47-3,72010-12-9,72010-13-0)

Guidance literature:

With 18-crown-6 ether; (COCl₂)2; In hexane; at -10 - -5 ℃;

DOI:10.1016/S0040-4039(00)86018-9

Reference yield:

((1R,2S,5R)-2-Isopropyl-5-methyl-cyclohexyloxy)-acetic acid (4R,5R)-4-[2-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxy)-acetoxy]-4,5-dihydro-benzo[def]chrysen-5-yl ester (78031-10-4,78088-16-1) → C20H12O (37574-47-3,64437-52-1,72010-12-9,72010-13-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 1 N NaOH / methanol / 1.5 h / 0 °C

With sodium hydroxide; In methanol;

DOI:10.1016/0040-4039(81)80111-6

Reference yield:

4(R),5(R)-4,5-dihydrobenzopyrene-4,5-diol (62600-10-6) → C20H12O (37574-47-3,64437-52-1,72010-12-9,72010-13-0)

Guidance literature:

DOI:10.1016/0040-4039(81)80111-6

upstream raw materials:

benzopyrene

4(R),5(R)-4,5-dihydrobenzopyrene-4,5-diol

((1R,2S,5R)-2-Isopropyl-5-methyl-cyclohexyloxy)-acetic acid (4R,5R)-4-[2-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxy)-acetoxy]-4,5-dihydro-benzo[def]chrysen-5-yl ester

Downstream raw materials:

5-hydroxy-benzo[a]pyrene

4-hydroxybenzoanthracene

(+/-)-trans-4-methoxy-5-hydroxy-4,5-dihydrobenzopyrene

(+/-)-trans-4-hydroxy-5-methoxy-4,5-dihydrobenzopyrene

Refernces

• 1、 Nagano, Tetsuo,Yokoohji, Kiyomi,Hirobe, Masaaki. "DIRECT EPOXIDATION OF POLYCYCLIC AROMATIC COMPOUNDS BY SUPEROXIDE IN THE PRESENCE OF PHOSGENE DIMER". . p. 3481 - 3484. Retrieved 2007/10/02.
• 2、 Okamoto,Shudo,Miyata,Kitahara,Nagata. "Reactions of K-region oxides of carcinogenic and noncarcinogenic aromatic hydrocarbons. Comparative studies on reactions with nucleophiles and acid-catalyzed reactions.". . p. 2014 - 2016. Retrieved 2007/10/05.