trans-Benzo(j)fluoranthene-9,10-diol

Base Information

• Chemical Name: trans-Benzo(j)fluoranthene-9,10-diol
• CAS No.: 76479-14-6
• Molecular Formula: C₂₀H₁₄O₂
• Molecular Weight: 286.33
• Nikkaji Number: J535.506K
• Mol file: 76479-14-6.mol

Synonyms:76479-14-6;CCRIS 8255;trans-Benzo(j)fluoranthene-9,10-diol;trans-9,10-Dihydrobenzo(j)fluoranthene-9,10-diol;Benzo(j)fluoranthene-9,10-diol, 9,10-dihydro-, trans-;TRANS-9,10-DIHYDRO-9,10-DIHYDROXYBENZO[J]FLUORANTHENE

Chemical Property of trans-Benzo(j)fluoranthene-9,10-diol

Chemical Property:

• Vapor Pressure: 4.47E-13mmHg at 25°C
• Boiling Point: 553.3°Cat760mmHg
• Flash Point: 268.6°C
• Density: 1.46g/cm³
• XLogP3: 3.4
• 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(C3=CC=C2)C5=C(C=C4)C(C(C=C5)O)O
• Isomeric SMILES: C1=CC2=C3C(=C1)C4=C(C3=CC=C2)C5=C(C=C4)[C@@H]([C@H](C=C5)O)O

Technology Process of trans-Benzo(j)fluoranthene-9,10-diol

There total 15 articles about trans-Benzo(j)fluoranthene-9,10-diol 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: 58.0%

benzofluoranthene-9,10-dione (106542-97-6) → trans-9,10-dihydro-9,10-dihydroxybenzofluoranthene (76479-14-6)

Guidance literature:

With potassium borohydride; oxygen; In ethanol; for 2h;

DOI:10.1021/jo00381a025

Reference yield: 24.0%

trans-9,10-bis(benzoyloxy)-9,10-dihydrobenzofluoranthene (77061-17-7) → trans-9,10-dihydro-9,10-dihydroxybenzofluoranthene (76479-14-6)

Guidance literature:

With sodium methylate; In tetrahydrofuran; methanol; for 0.5h; Ambient temperature;

DOI:10.1021/jo00325a028

Reference yield:

7-methyl-6b,7,10,10a-tetrahydrofluoranthene (77096-72-1) → trans-9,10-dihydro-9,10-dihydroxybenzofluoranthene (76479-14-6)

Guidance literature:

Multi-step reaction with 14 steps

1: 80 percent / DDQ / xylene / 5 h / Heating

2: 80 percent / N-bromosuccinimide, benzoyl peroxide / CCl₄ / 3 h / Heating

3: 78 percent / diethyl ether / 30 h / Heating

4: 1.) diborane, 2.) 30percent H₂O₂ / 1.) THF, from 0 deg C to room temp., 8 h, 2.) reflux, 1 h

5: pyridinium chlorochromate / CH₂Cl₂ / 1 h / 20 °C

6: 85 percent / AgNO₃, 1.5 KOH / ethanol; H₂O / 2 h

7: SOCl₂ / benzene / 3 h / Heating

8: 1.) AlCl₃ / CS₂ / 1.) 0 deg C, 2.) reflux, 10 min

9: LiAlH₄ / tetrahydrofuran / 0.33 h / 20 °C

10: 60 percent / conc. H₂SO₄ / acetic acid / 3 h / 60 °C

11: 62 percent / 1.) I₂ / benzene / 1.) reflux, 2.) reflux, 2.5 h

12: 30 percent / N-bromsuccinimide, α,α'-azobis(isobutyronitrile) / CCl4 / 2 h / Heating

13: 60 percent / 1,5-diazabicyclo<4.3.0>non-5-ene / tetrahydrofuran / 3 h / 0 °C

14: 24 percent / sodium methoxide / tetrahydrofuran; methanol / 0.5 h / Ambient temperature

With potassium hydroxide; N-Bromosuccinimide; lithium aluminium tetrahydride; aluminium trichloride; thionyl chloride; Perbenzoic acid; sulfuric acid; azobisisobutyronitrile; DBN; dihydrogen peroxide; iodine; sodium methylate; silver nitrate; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; diborane; In tetrahydrofuran; methanol; carbon disulfide; tetrachloromethane; diethyl ether; ethanol; dichloromethane; water; acetic acid; xylene; benzene;

DOI:10.1021/jo00325a028

upstream raw materials:

trans-9,10-bis(benzoyloxy)-9,10-dihydrobenzofluoranthene

benzofluoranthene-9,10-dione

7-methyl-6b,7,10,10a-tetrahydrofluoranthene

7-methylfluoranthene

Refernces

• 1、 Amin, Shantilal,Bedenko, Victoria,LaVoie, Edmond,Hecht, Stephen S.,Hoffmann, Dietrich. "Synthesis of Dihydro Diols as Potential Proximate Carcinogens of Benzofluoranthenes". . p. 2573 - 2578. Retrieved 2007/10/02.