2-Hydroxybenzo(a)pyrene

Base Information

• Chemical Name: 2-Hydroxybenzo(a)pyrene
• CAS No.: 56892-30-9
• Molecular Formula: C₂₀H₁₂O
• Molecular Weight: 268.315
• UNII: 4A8M3AM5S4
• DSSTox Substance ID: DTXSID80205415
• Nikkaji Number: J65.901K
• Wikidata: Q27115968
• ChEMBL ID: CHEMBL1908011
• Mol file: 56892-30-9.mol

Synonyms:2-hydroxybenzo(a)pyrene;2-hydroxybenzo(a)pyrene, 3H-labeled;2-hydroxybenzo(a)pyrene, hydrogen sulfate;benzo(a)pyren-2-ol

Chemical Property of 2-Hydroxybenzo(a)pyrene

Chemical Property:

• Vapor Pressure: 9.85E-12mmHg at 25°C
• Melting Point: 227.5°C
• Refractive Index: 1.6220 (estimate)
• Boiling Point: 527.2°Cat760mmHg
• PKA: 9.57±0.30(Predicted)
• Flash Point: 252.9°C
• PSA: 20.23000
• Density: 1.379g/cm³
• LogP: 5.44280
• XLogP3: 5.6
• 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

2-HYDROXYBENZO(A)PYRENE 95.00% ^*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=CC(=CC(=C54)C=C3)O

Technology Process of 2-Hydroxybenzo(a)pyrene

There total 13 articles about 2-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:

(10bR,12aS)-1,6,10b,11,12,12a-Hexahydro-benzo[def]chrysene → benzo[a]pyren-2-ol (56892-30-9)

Guidance literature:

Multi-step reaction with 3 steps

1: AcNHBr, LiOAc

2: (i) NaOMe, (ii) BF₃-Et₂O

3: Pd / (heating)

With lithium acetate; N-bromoacetamide; palladium;

DOI:10.1021/jo00868a017

Reference yield:

(10bR,12aS)-1,6,10b,11,12,12a-Hexahydro-2H-benzo[def]chrysen-3-one → benzo[a]pyren-2-ol (56892-30-9)

Guidance literature:

Multi-step reaction with 4 steps

1: (i) NaBH₄, MeOH, (ii) aq. HCl, AcOH

2: AcNHBr, LiOAc

3: (i) NaOMe, (ii) BF₃-Et₂O

4: Pd / (heating)

With lithium acetate; N-bromoacetamide; palladium;

DOI:10.1021/jo00868a017

Reference yield:

2-(6-methoxynaphthalen-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane (1022094-56-9) → benzo[a]pyren-2-ol (56892-30-9)

Guidance literature:

Multi-step reaction with 9 steps

1.1: palladium diacetate; potassium carbonate; triphenylphosphine / 1,2-dimethoxyethane; water / 20 °C / Inert atmosphere

1.2: 23 h / Inert atmosphere; Reflux

2.1: monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium⁽⁰⁾ / tetrahydrofuran / 20 °C / Inert atmosphere

3.1: sodium hydroxide / ethanol; water / 1 h / Reflux

4.1: methanesulfonic acid / 1 h / 50 °C

5.1: pyridine / dichloromethane / 0.17 h / 20 °C

5.2: -78 - 20 °C

6.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere

7.1: methanol; potassium carbonate / tetrahydrofuran / 1 h / 20 °C

8.1: platinum(II) chloride / toluene / 80 °C

9.1: boron tribromide

With pyridine; methanol; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; methanesulfonic acid; palladium diacetate; boron tribromide; potassium carbonate; triethylamine; triphenylphosphine; platinum(II) chloride; sodium hydroxide; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; 1.2: Suzuki-Miyaura cross-coupling / 2.1: Hartwig cross-coupling / 6.1: Sonogashira cross-coupling;

DOI:10.1016/j.tet.2012.05.130

upstream raw materials:

2-(6-methoxynaphthalen-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane

2-methoxy-5-(trimethylsilylethynyl)chrysene

2-(6-methoxynaphthalen-2-yl)phenylacetic acid

2-methoxychrysen-5-ol

Refernces