1-Nitrobenzo(a)pyrene trans-7,8-dihydrodiol

Base Information

• Chemical Name: 1-Nitrobenzo(a)pyrene trans-7,8-dihydrodiol
• CAS No.: 88598-59-8
• Molecular Formula: C₂₀H₁₃NO₄
• Molecular Weight: 331.328
• DSSTox Substance ID: DTXSID101008254
• Wikidata: Q83004651
• NCI Thesaurus Code: C29780
• Mol file: 88598-59-8.mol

Synonyms:1-nitrobenzo(a)pyrene-trans-7,8-dihydrodiol

Chemical Property of 1-Nitrobenzo(a)pyrene trans-7,8-dihydrodiol

Chemical Property:

• Vapor Pressure: 4.33E-16mmHg at 25°C
• Boiling Point: 617.2°C at 760 mmHg
• Flash Point: 254°C
• Density: 1.593g/cm³
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 331.08445790
• Heavy Atom Count: 25
• Complexity: 587

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC2=C(C=C3C=CC4=C5C3=C2C=CC5=C(C=C4)[N+](=O)[O-])C(C1O)O
• Isomeric SMILES: C1=CC2=C(C=C3C=CC4=C5C3=C2C=CC5=C(C=C4)[N+](=O)[O-])[C@@H]([C@H]1O)O

Technology Process of 1-Nitrobenzo(a)pyrene trans-7,8-dihydrodiol

There total 8 articles about 1-Nitrobenzo(a)pyrene trans-7,8-dihydrodiol 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: 92.0%

7,8-Dihydroxy-7,8-dihydro-1-nitrobenzopyrene trans-7,8-diacetate → trans-7,8-Dihydroxy-7,8-dihydro-1-nitrobenzopyrene (88598-59-8)

Guidance literature:

With sodium methylate; In tetrahydrofuran; methanol; at 65 ℃; for 0.5h;

DOI:10.1021/jo00077a063

Reference yield:

9,10-dihydrobenzo[a]pyren-(8H)-none (3331-46-2) → trans-7,8-Dihydroxy-7,8-dihydro-1-nitrobenzopyrene (88598-59-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 41 percent / N₂O₄ / CH₂Cl₂

2: 96 percent / NaBH₄ / tetrahydrofuran; methanol / 0.67 h / Ambient temperature

3: 98 percent / p-toluenesulfonic acid / benzene / 1.67 h / Heating

4: 59 percent / I₂ / benzene / 18 h / Heating

5: 90 percent / NaOCH₃ / tetrahydrofuran; methanol / 0.5 h / 65 °C

6: 91 percent / pyridine / Ambient temperature

7: DDQ / dioxane / 54 h / Heating

8: 92 percent / NaOCH₃ / tetrahydrofuran; methanol / 0.5 h / 65 °C

With pyridine; sodium tetrahydroborate; iodine; sodium methylate; dinitrogen tetraoxide; toluene-4-sulfonic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; benzene;

DOI:10.1021/jo00077a063

Reference yield:

9,10-Dihydro-1-nitrobenzopyrene (132929-89-6) → trans-7,8-Dihydroxy-7,8-dihydro-1-nitrobenzopyrene (88598-59-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 59 percent / I₂ / benzene / 18 h / Heating

2: 90 percent / NaOCH₃ / tetrahydrofuran; methanol / 0.5 h / 65 °C

3: 91 percent / pyridine / Ambient temperature

4: DDQ / dioxane / 54 h / Heating

5: 92 percent / NaOCH₃ / tetrahydrofuran; methanol / 0.5 h / 65 °C

With pyridine; iodine; sodium methylate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; 1,4-dioxane; methanol; benzene;

DOI:10.1021/jo00077a063

upstream raw materials:

9,10-dihydrobenzo[a]pyren-(8H)-none

9,10-Dihydro-1-nitrobenzopyrene

7-Hydroxy-7,8,9,10-tetrahydro-1-nitrobenzopyrene

1-Nitro-9,10-dihydrobenzopyren-7(8H)-one

Refernces