3-Hydroxybenzo(a)pyrene

Base Information

• Chemical Name: 3-Hydroxybenzo(a)pyrene
• CAS No.: 13345-21-6
• Molecular Formula: C₂₀H₁₂O
• Molecular Weight: 268.315
• Hs Code.: 29062990
• UNII: 672ICH1Q4L
• DSSTox Substance ID: DTXSID7038319
• Nikkaji Number: J2.737E
• Wikidata: Q26840846
• ChEMBL ID: CHEMBL8020
• Mol file: 13345-21-6.mol

Synonyms:3-hydroxybenzo(a)pyrene;3-hydroxybenzo(a)pyrene, 3H-labeled;3-OH-BaP;3-OH-BP;benzo(a)pyren-3-ol

Chemical Property of 3-Hydroxybenzo(a)pyrene

Chemical Property:

• Vapor Pressure: 9.85E-12mmHg at 25°C
• Melting Point: 186-188°C
• Refractive Index: 1.6220 (estimate)
• Boiling Point: 527.2°Cat760mmHg
• PKA: 9.40±0.30(Predicted)
• Flash Point: 252.9°C
• PSA: 20.23000
• Density: 1.379g/cm³
• LogP: 5.44280
• Storage Temp.: 2-8°C
• XLogP3: 5.9
• 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

3-HydroxyBenzopyrene ^*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=C2C3=C4C(=CC2=C1)C=CC5=C(C=CC(=C54)C=C3)O
• Uses: A metabolite of Benzopyrene (BaP), a carcinogenic component of tobacco smoke implicated in lung cancer.

Technology Process of 3-Hydroxybenzo(a)pyrene

There total 34 articles about 3-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: 75.0%

3-methoxybenzopyrene (63059-68-7) → 3-hydroxybenzo[a]pyrene (13345-21-6)

Guidance literature:

With hydrogen iodide; acetic acid; at 140 ℃; for 1.5h; Inert atmosphere;

DOI:10.1021/jo801864m

Reference yield:

3-acetoxybenzopyrene (123125-95-1) → 3-hydroxybenzo[a]pyrene (13345-21-6)

Guidance literature:

With potassium carbonate; In tetrahydrofuran; methanol; at 0 ℃; for 0.5h;

DOI:10.1021/jo00283a020

Reference yield:

1-methoxypyrene-6-carboxaldehyde (93656-81-6) → 3-hydroxybenzo[a]pyrene (13345-21-6)

Guidance literature:

Multi-step reaction with 13 steps

1: 97 percent / pyridine, piperidine / 1.) from 80 deg C to 85 deg C, 30 min, 2.) reflux, 4 h

2: 98 percent / H₂ / 10percent Pd/C / tetrahydrofuran / 5 h / 1810.02 Torr

3: 99.7 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / Heating

4: 98.6 percent / Et₃N / CH₂Cl₂ / 0.25 h / 0 - 5 °C

5: aq. tricaprylylmethylammonium chloride / benzene / 15 h / Heating

6: aq. KOH / ethane-1,2-diol / 8 h / Heating

7: 53 percent / polyphosphoric acid / 2 h / 100 - 105 °C

8: 48percent aq. HBr, CH₃CO₂H / 2 h / Heating

9: NaBH₄ / ethanol / 0.5 h

10: p-toluenesulfonic acid / benzene / 1 h / Heating

11: pyridine / 3 h

12: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / dioxane / 1 h / Heating

13: K₂CO₃ / methanol; tetrahydrofuran / 0.5 h / 0 °C

With piperidine; pyridine; potassium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; PPA; hydrogen bromide; hydrogen; Aliquat 336; potassium carbonate; toluene-4-sulfonic acid; acetic acid; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; ethylene glycol; benzene;

DOI:10.1021/jo00283a020

upstream raw materials:

benzopyrene

1,6,10b,11,12,12a-hexahydro-2H-benzo[def]chrysen-3-one

3-acetoxybenzopyrene

potassium benzopyren-3-yl sulfate

Downstream raw materials:

3-methoxybenzopyrene

potassium benzopyren-3-yl sulfate