8-Hydroxybenzo[a]pyrene

Base Information

• Chemical Name: 8-Hydroxybenzo[a]pyrene
• CAS No.: 13345-26-1
• Molecular Formula: C₂₀H₁₂O
• Molecular Weight: 268.315
• Hs Code.: 2906299090
• DSSTox Substance ID: DTXSID00158116
• Nikkaji Number: J961J
• Wikidata: Q27116106
• ChEMBL ID: CHEMBL1908057
• Mol file: 13345-26-1.mol

Synonyms:benzo[a]pyren-8-ol;13345-26-1;8-Hydroxybenzo[a]pyrene;Benzo(a)pyren-8-ol;8-Hydroxy-benzo(a)pyrene;BENZO(a)PYRENE, 8-HYDROXY-;8-Hydroxy-3,4-benzopyrene;Benzo[pqr]tetraphen-8-ol;BRN 2379758;CHEBI:34493;8-HYDROXYBENZO(A)PYRENE;8-Hydroxy benzo[a]pyrene;BIDD:ER0355;CHEMBL1908057;DTXSID00158116;AKOS015905883;LS-40025;CS-0098958;Q27116106;pentacyclo[10.6.2.0?,?.0?,??.0??,??]icosa-1(18),2,4,6,8,10,12,14,16,19-decaen-5-ol

Chemical Property of 8-Hydroxybenzo[a]pyrene

Chemical Property:

• Vapor Pressure: 9.85E-12mmHg at 25°C
• Boiling Point: 527.2°Cat760mmHg
• Flash Point: 252.9°C
• PSA: 20.23000
• Density: 1.379g/cm³
• LogP: 5.44280
• XLogP3: 5.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 268.088815002
• Heavy Atom Count: 21
• Complexity: 405

Purity/Quality:

99% ^*data from raw suppliers

Benzo[a]pyren-8-ol ^*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(=C5)O)C=C2
• Uses: Benzo[a]pyren-8-ol is a metabolite of Benzopyrene (B205800) with antiestrogenic activity. Benzo[a]pyren-8-ol is also a useful synthetic intermediate in the synthesis of Benzo[a]pyrene-7,8-diol (B205840).

Technology Process of 8-Hydroxybenzo[a]pyrene

There total 19 articles about 8-Hydroxybenzo[a]pyrene 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: 86.0%

3-methoxybenzopyrene (17573-31-8) → 7-hydroxy benzopyrene (13345-26-1)

Guidance literature:

With boron tribromide; In dichloromethane; at -20 - 20 ℃;

DOI:10.1021/jo030348n

Reference yield:

(6-methoxynaphthalen-1-yl)boronic acid → 7-hydroxy benzopyrene (13345-26-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 91 percent / Pd(PPh₃)4; aq. Na₂CO₃ / ethanol; 1,2-dimethoxy-ethane / Heating

2: 95 percent / t-BuOK / diethyl ether; tetrahydrofuran / 20 °C

3: 88 percent / MeSO₃H / CH₂Cl₂ / 0 °C

4: 86 percent / BBr₃ / CH₂Cl₂ / -20 - 20 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; methanesulfonic acid; potassium tert-butylate; boron tribromide; sodium carbonate; In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; ethanol; dichloromethane; 1: Suzuki coupling / 2: Wittig reaction;

DOI:10.1021/jo030348n

Reference yield:

2-(2-methoxynaphthalen-6-yl)benzene-1,3-dialdehyde (671780-69-1) → 7-hydroxy benzopyrene (13345-26-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / t-BuOK / diethyl ether; tetrahydrofuran / 20 °C

2: 88 percent / MeSO₃H / CH₂Cl₂ / 0 °C

3: 86 percent / BBr₃ / CH₂Cl₂ / -20 - 20 °C

With methanesulfonic acid; potassium tert-butylate; boron tribromide; In tetrahydrofuran; diethyl ether; dichloromethane; 1: Wittig reaction;

DOI:10.1021/jo030348n

upstream raw materials:

(-)-trans-7,8-dihydroxy-7,8-dihydrobenzo[a]pyrene

9,10-dihydrobenzopyren-8(7H)-one

3-methoxybenzopyrene

2-(2-methoxynaphthalen-6-yl)benzene-1,3-dialdehyde

Downstream raw materials:

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

7,8-dihydroxy-7,8,9,10-tetrahydrobenzo[a]pyrene

7,8-Dihydroxybenzo[a]pyrene

(-)-trans-7,8-dihydroxy-7,8-dihydrobenzo[a]pyrene

Refernces

• 1、 Harvey, Ronald G.,Dai, Qing,Ran, Chongzhao,Penning, Trevor M.. "Synthesis of the o-Quinones and Other Oxidized Metabolites of Polycyclic Aromatic Hydrocarbons Implicated in Carcinogenesis". . p. 2024 - 2032. Retrieved 2007/10/03.