Benzo[c]phenanthren-1-ol

Base Information

• Chemical Name: Benzo[c]phenanthren-1-ol
• CAS No.: 22717-93-7
• Molecular Formula: C₁₈H₁₂O
• Molecular Weight: 244.293
• NSC Number: 97675
• DSSTox Substance ID: DTXSID20294681
• Nikkaji Number: J1.684.622H
• Wikidata: Q27225546
• Metabolomics Workbench ID: 87149
• Mol file: 22717-93-7.mol

Synonyms:Benzo[c]phenanthren-1-ol;22717-93-7;1-hydroxybenzo[c]phenanthrene;Benzo(c)phenanthren-1-ol;NSC 97675;NSC97675;1-benzo[c]phenanthrenol;hydroxybenzo[c]phenanthrene;Benzo[c]phenanthrene-1-ol;SCHEMBL2467605;DTXSID20294681;CHEBI:132377;NSC-97675;Q27225546

Chemical Property of Benzo[c]phenanthren-1-ol

Chemical Property:

• Vapor Pressure: 1.5E-10mmHg at 25°C
• Boiling Point: 498.2°Cat760mmHg
• Flash Point: 240.4°C
• Density: 1.284g/cm³
• XLogP3: 5.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 244.088815002
• Heavy Atom Count: 19
• Complexity: 326

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C=CC3=C2C4=C(C=CC=C4O)C=C3

Technology Process of Benzo[c]phenanthren-1-ol

There total 9 articles about Benzo[c]phenanthren-1-ol 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: 88.0%

1-methoxybenzo[c]phenathrene (4235-05-6) → 1-Hydroxy-benzophenanthren (22717-93-7)

Guidance literature:

With boron tribromide; In dichloromethane; at 20 ℃;

DOI:10.1016/j.tetlet.2007.07.105

Reference yield: 30.0%

trimethylsilyl trifluoromethanesulfonate (27607-77-8) + 1,4-dihydro-1,4-epoxybenzophenanthrene → 1-Hydroxy-benzophenanthren (22717-93-7)

Guidance literature:

In tetrahydrofuran; at 0 - 20 ℃; for 2h; Inert atmosphere; Schlenk technique;

DOI:10.1021/jacs.1c05434

Reference yield:

1-bromo-2-naphthol (573-97-7) → 1-Hydroxy-benzophenanthren (22717-93-7)

Guidance literature:

Multi-step reaction with 7 steps

1.1: pyridine / dichloromethane / 0.25 h / 0 °C / Inert atmosphere; Schlenk technique

2.1: methyllithium / diethyl ether; tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere; Schlenk technique

2.2: 10 h / 30 °C / Inert atmosphere; Schlenk technique

3.1: pyridinium p-toluenesulfonate / dichloromethane / 20 h / 20 °C / Inert atmosphere; Schlenk technique

4.1: n-butyllithium / tetrahydrofuran; hexane / 0.75 h / 20 °C / Inert atmosphere; Schlenk technique

4.2: 14 h / Inert atmosphere; Schlenk technique

4.3: 1 h / 20 °C / Inert atmosphere; Schlenk technique

5.1: tetrahydrofuran / 5.5 h / 0 - 20 °C / Inert atmosphere; Schlenk technique

6.1: methyllithium / diethyl ether; tetrahydrofuran / 15.5 h / -78 - 20 °C / Inert atmosphere; Schlenk technique

7.1: tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere; Schlenk technique

With pyridine; n-butyllithium; methyllithium; pyridinium p-toluenesulfonate; In tetrahydrofuran; diethyl ether; hexane; dichloromethane;

DOI:10.1021/jacs.1c05434

upstream raw materials:

1-methoxybenzo[c]phenathrene

1-bromo-2-naphthol

trifluoromethanesulfonic acid 1-bromonaphthalen-2-yl ester

4-phenanthrol

Downstream raw materials:

1-Amino-benzophenanthren

Refernces

• 1、 Storch, Jan,?ermák, Jan,Karban, Jind?ich. "Synthesis of 1-(2-ethynyl-6-methylphenyl)- and 1-(2-ethynyl-6-methoxyphenyl)-naphthalene and their cyclization". . p. 6814 - 6816. Retrieved 2008/03/12.