9,10-Dihydroxy-9,10-dihydrobenzo(e)pyrene

Base Information

• Chemical Name: 9,10-Dihydroxy-9,10-dihydrobenzo(e)pyrene
• CAS No.: 88190-97-0
• Molecular Formula: C₂₀H₁₄O₂
• Molecular Weight: 286.33
• Mol file: 88190-97-0.mol

Synonyms:9,10-dihydroxy-9,10-dihydrobenzo(e)pyrene;9,10-dihydroxy-9,10-dihydrobenzo(e)pyrene, (trans)-(+-)-isomer;9,10-dihydroxy-9,10-dihydrobenzo(e)pyrene, (trans)-isomer;benzo(e)pyrene-trans-9,10-dihydrodiol;trans-9,10-dihydro-9,10-dihydroxybenzo(e)pyrene;trans-9,10-dihydroxy-9,10-dihydrobenzo(e)pyrene

Chemical Property of 9,10-Dihydroxy-9,10-dihydrobenzo(e)pyrene

Chemical Property:

• Vapor Pressure: 4.47E-13mmHg at 25°C
• Refractive Index: 1.7580 (estimate)
• Boiling Point: 553.3°C at 760 mmHg
• Flash Point: 268.6°C
• PSA: 40.46000
• Density: 1.46g/cm³
• LogP: 4.00510
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 286.099379685
• Heavy Atom Count: 22
• Complexity: 472

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC2=C3C(=C1)C4=C(C(C(C=C4)O)O)C5=CC=CC(=C53)C=C2

Technology Process of 9,10-Dihydroxy-9,10-dihydrobenzo(e)pyrene

There total 15 articles about 9,10-Dihydroxy-9,10-dihydrobenzo(e)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: 35.0%

1-((9R,10S)-10-Acetyl-9,10-dihydro-benzo[e]pyren-9-yl)-ethanone → trans-9,10-Dihydroxy-9,10-dihydrobenzopyren (66788-06-5,88190-97-0)

Guidance literature:

With sodium methylate; In tetrahydrofuran; methanol;

DOI:10.1021/jo00150a027

Reference yield:

benzopyrene-9,10-dione (82120-24-9) → trans-9,10-Dihydroxy-9,10-dihydrobenzopyren (66788-06-5,88190-97-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) NaBH₄ / 1.) ethanol, room temp., 1 week, 2.) pyridine

2: 35 percent / NaOMe / tetrahydrofuran; methanol

With sodium tetrahydroborate; sodium methylate; In tetrahydrofuran; methanol;

DOI:10.1021/jo00150a027

Reference yield:

1,2,3,6,7,8,9,10-Octahydrobenzopyrene (68151-10-0) → trans-9,10-Dihydroxy-9,10-dihydrobenzopyren (66788-06-5,88190-97-0)

Guidance literature:

Multi-step reaction with 5 steps

1: I₂ / benzene / Heating

2: DDQ

3: NBS, (PhCO)2O₂

4: DBN

5: NaOMe

With N-Bromosuccinimide; 2,6-dichloro-benzonitrile; iodine; sodium methylate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; dibenzoyl peroxide; In benzene;

DOI:10.1021/jo01315a019

upstream raw materials:

benzopyrene-9,10-dione

1,2,3,6,7,8,9,10-Octahydrobenzopyrene

9,10-Dihydrobenzopyrene

9-Hydroxy-9,10,11,12-tetrahydrobenzopyrene

Refernces

• 1、 Lehr,Taylor,Kumar,et al.. "Synthesis of the non-K-region and K-region trans-dihydrodiols of benzo[e]pyrene". . p. 3462 - 3466. Retrieved 2007/10/11.