9-Diazo-4,5-methylene-10-oxophenanthrene

Base Information

• Chemical Name: 9-Diazo-4,5-methylene-10-oxophenanthrene
• CAS No.: 24153-37-5
• Molecular Formula: C₁₅H₈N₂O
• Molecular Weight: 232.241
• DSSTox Substance ID: DTXSID00178854
• Wikidata: Q83049341
• Mol file: 24153-37-5.mol

Synonyms:9-Diazo-4,5-methylene-10-oxophenanthrene;24153-37-5;DTXSID00178854

Chemical Property of 9-Diazo-4,5-methylene-10-oxophenanthrene

Chemical Property:

• XLogP3: 5.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 232.063662883
• Heavy Atom Count: 18
• Complexity: 401

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2=C3C(=CC=C2)C(=C(C4=CC=CC1=C43)[O-])[N+]#N

Technology Process of 9-Diazo-4,5-methylene-10-oxophenanthrene

There total 2 articles about 9-Diazo-4,5-methylene-10-oxophenanthrene 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:

4H-Cyclopenta[def]phenanthrene (203-64-5) → 9-diazo-8,9-dihydro-4H-cyclopentaphenanthren-8-one (24153-37-5)

Guidance literature:

Multi-step reaction with 2 steps

1: HIO₃, aq. AcOH / dioxane

2: TsNHNH₂

With iodic acid; acetic acid; toluene-4-sulfonic acid hydrazide; In 1,4-dioxane;

DOI:10.1021/ja00711a087

Reference yield:

4H-cyclopentaphenanthrene-8,9-dione (27018-91-3) → 9-diazo-8,9-dihydro-4H-cyclopentaphenanthren-8-one (24153-37-5)

Guidance literature:

With toluene-4-sulfonic acid hydrazide;

DOI:10.1021/ja00711a087 DOI:10.1021/ja00842a022

Reference yield: 58.5%

9-diazo-8,9-dihydro-4H-cyclopentaphenanthren-8-one (24153-37-5) + benzene (71-43-2,26181-88-4,54682-86-9,13967-78-7,174973-66-1) → 9-Phenyl-4H-cyclopenta[def]phenanthren-8-ol

Guidance literature:

for 2.5h; Irradiation;

DOI:10.1039/P29960002303

upstream raw materials:

4H-cyclopentaphenanthrene-8,9-dione

4H-Cyclopenta[def]phenanthrene

Downstream raw materials:

8a,12a-dihdyro-4H-benzocyclopenta<4,4a,4b,5>phenanthro<9,10-d>furan

cyclopenta[def]fluorene-4,8-dione