Fulvalene

Base Information

• Chemical Name: Fulvalene
• CAS No.: 91-12-3
• Molecular Formula: C₁₀H₈
• Molecular Weight: 128.174
• UNII: V2K3QQS6YW
• DSSTox Substance ID: DTXSID10447902
• Nikkaji Number: J247.849H
• Wikipedia: Fulvalene
• Wikidata: Q415358
• Metabolomics Workbench ID: 58018
• Mol file: 91-12-3.mol

Synonyms:fulvalene;bicyclopentadienylidene;Pentafulvalene;91-12-3;fulvaleno;Fulvalen;V2K3QQS6YW;[5,5']bicyclopentadienylidene;1,1'-bi[cylopentadienylidene];1,1'-Bi(cylopentadienylidene);5-(2,4-cyclopentadien-1-ylidene)-1,3-cyclopentadiene;BI-2,4-cyclopentadien-1-ylidene;UNII-V2K3QQS6YW;1,3-Cyclopentadiene, 5-(2,4-cyclopentadien-1-ylidene)-;1,1'-bi(cyclopenta-2,4-dien-1-ylidene);5-cyclopenta-2,4-dien-1-ylidenecyclopenta-1,3-diene;CHEBI:51994;DTXSID10447902;Q415358

Chemical Property of Fulvalene

Chemical Property:

• PSA: 0.00000
• LogP: 2.53500
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 128.062600255
• Heavy Atom Count: 10
• Complexity: 225

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=CC=C2)C=C1

Technology Process of Fulvalene

There total 15 articles about Fulvalene 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: 73.0%

dilithium bi(cyclopentadienyl)diid → fulvalene (91-12-3)

Guidance literature:

With copper dichloride; In tetrahydrofuran; at -78 ℃; for 0.75h;

DOI:10.1002/hlca.19860690719

Reference yield: 41.0%

4-methyleneoxetan-2-one (674-82-8,2130-41-8) + 5-diazo-1,3-cyclopentadiene (1192-27-4) → fulvalene (91-12-3) + 1-Oxadispiro[3.0.4.1]deca-6,8-dien-2-one

Guidance literature:

dirhodium tetraacetate; In benzene;

DOI:10.1039/b001393p

Reference yield:

C37H68O2Sn2 → fulvalene (91-12-3)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane-d2; at -78 ℃;

DOI:10.1021/jo030368p

upstream raw materials:

9,10-dihydrofulvalene

ethene

5-diazo-1,3-cyclopentadiene

carbon monoxide

Refernces

Synthetic and Theoretical Studies of Cyclobuta[1,2:3,4]dicyclopentene. Organocobalt Intermediates in the Construction of the Unsaturated Carbon Skeleton and Their Transformation into Novel Cobaltacyclic Complexes by C-C Insertion

10.1021/jo030368p

The research focuses on the theoretical and synthetic studies of cyclobuta[1,2:3,4]dicyclopentene (1), a tricyclic 10π-electron hydrocarbon that has never been synthesized. The study uses density-functional-theory calculations to predict the structure and properties of 1, finding it to be a D2h symmetric structure with nonalternant C-C bonds and significant aromatic character. The research explores potential synthetic pathways to 1, starting from tricyclic carbonate 11 and distannane 12, which led to the formation of the unstable hydrocarbon bicyclopentadienylidene (13). The study also investigates cobalt-cyclobutadiene complexes 18 and 19 as potential precursors to 1. Treatment of 18 with methyllithium resulted in the novel cobaltacyclic product 30, while dehydration of 19 in the presence of pyridine produced the ring-opening cobaltacyclic product 35. These findings suggest that the transformations may involve a 10-electron electrocyclic ring-opening reaction, similar to the hypothetical transformation of tetraene 8 to bicyclopentadienylidene (13).