1,2,3,4,5-Pentamethylcyclopentadiene

Base Information

• Chemical Name: 1,2,3,4,5-Pentamethylcyclopentadiene
• CAS No.: 4045-44-7
• Molecular Formula: C10H16
• Molecular Weight: 136.237
• Hs Code.: 29021990
• European Community (EC) Number: 223-743-4
• NSC Number: 222823
• UNII: DSE3MRZ77C
• DSSTox Substance ID: DTXSID00193466
• Nikkaji Number: J217.859A
• Wikipedia: Pentamethylcyclopentadiene
• Wikidata: Q1927394
• Mol file: 4045-44-7.mol

Synonyms:1,2,3,4,5-pentamethyl-cyclopentadiene;1,2,3,4,5-pentamethylcyclopentadiene

Chemical Property of 1,2,3,4,5-Pentamethylcyclopentadiene

Chemical Property:

• Appearance/Colour: clear colorless to yellowish liquid
• Vapor Pressure: 1.97mmHg at 25°C
• Melting Point: 236oC
• Refractive Index: n20/D 1.474(lit.)
• Boiling Point: 170.2 °C at 760 mmHg
• Flash Point: 44.4 °C
• PSA: 0.00000
• Density: 0.814 g/cm³
• LogP: 3.30890
• Storage Temp.: −20°C
• Sensitive.: Light Sensitive
• Water Solubility.: Miscible with methanol. dichloromethane and ethyl acetate. Slightly miscible with water.
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 136.125200510
• Heavy Atom Count: 10
• Complexity: 192

Purity/Quality:

99% ^*data from raw suppliers

1,2,3,4,5-Pentamethylcyclopentadiene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R10:
• Hazard Codes: R10:
• Statements: 10
• Safety Statements: 16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Aliphatics, Unsaturated
• Canonical SMILES: CC1C(=C(C(=C1C)C)C)C
• Uses: 1,2,3,4,5-Pentamethylcyclopentadiene serves as a precursor to the ligand 1,2,3,4,5-pentamethylcyclopentadienyl. It is used as a growth modifier chemical, during metal organic chemical vapor deposition of iron from iron pentacarbonyl. It is used as a ligand in "one-pot" iridium-catalyzed transformation of alcohols to amides. Further, it acts as an electron mediator in the regeneration process of nicotinamide adenine dinucleotide. In addition to this, it undergoes radical cation catalyzed cycloaddition reaction with allenes to get Diels-Alder product.

Technology Process of 1,2,3,4,5-Pentamethylcyclopentadiene

There total 101 articles about 1,2,3,4,5-Pentamethylcyclopentadiene 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: 98.0%

7-(1,2,3,4,5-pentamethyl-2,4-cyclopentadienyl)-7-tridecanol (874964-07-5) → tridecan-7-one (462-18-0) + 1,2,3,4,5-pentamethylcyclopentadiene (4045-44-7)

Guidance literature:

In toluene; for 30h; Heating;

DOI:10.1016/j.tet.2006.01.097

Reference yield: 97.0%

(4-buthoxyphenyl)(1,2,3,4,5-pentamethyl-2,4-cyclopentadienyl)methanol (862387-21-1) → 1,2,3,4,5-pentamethylcyclopentadiene (4045-44-7) + p-butoxybenzaldehyde (5736-88-9)

Guidance literature:

In toluene; at 110 ℃; for 3h;

DOI:10.1016/j.tet.2006.01.097

Reference yield: 86.0%

4-(buthoxyphenyl)(1,2,3,4,5-pentamethyl-2,4-cyclopentadienyl)(trimethylsiloxy)methane → 1,2,3,4,5-pentamethylcyclopentadiene (4045-44-7) + p-butoxybenzaldehyde (5736-88-9)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1016/j.tet.2006.01.097

upstream raw materials:

1,2,3,4,5,6-hexamethylbicyclo[2.2.0]hexa-2,5-diene

5-acetyl-1,2,3,4,5-pentamethylcyclopentadiene

2,3,4,5-tetramethyl-2-cyclopenten-1-one

methyllithium

Downstream raw materials:

3-Chlor-2,4,5,6-tetramethylbenzylchlorid

5-(benzylthio)-1,2,3,4,5-pentamethylcyclopentadiene

3-Brom-2,4,5,6-tetramethylbenzylbromid

1,3,4,5,8-Pentamethyl-2,6,7-trioxabicyclo<3.2.1>oct-3-ene

Refernces

• 1、 Hastings, Courtney J.,Backlund, Mikael P.,Bergman, Robert G.,Raymond, Kenneth N.. "Enzyme-like control of carbocation deprotonation regioselectivity in supramolecular catalysis of the nazarov cyclization". . p. 10570 - 10573. Retrieved 2011.
• 2、 Pinkas, Jiri,Cisarova, Ivana,Horacek, Michal,Kubista, Jiri,MacH, Karel. "Reactions of hydrogen sulfide with singly and doubly tucked-in titanocenes". . p. 1034 - 1045. Retrieved 2011.
• 3、 Wayda, Andrea L.,Evans. "Synthesis of a bis(pentamethylcyclopentadienyl) derivative of neodymium". . p. 2190 - 2191. Retrieved 1980.
• 4、 Mironov et al.. "". . p. 3997. Retrieved 1968.
• 5、 Shestakov, Boris G.,Mahrova, Tatyana V.,Larionova, Joulia,Long, Jêrome,Cherkasov, Anton V.,Fukin, Georgy K.,Lyssenko, Konstantin A.,Scherer, Wolfgang,Hauf, Christoph,Magdesieva, Tatiana V.,Levitskiy, Oleg A.,Trifonov, Alexander A.. "Ytterbium(III) Complexes Coordinated by Dianionic 1,4-Diazabutadiene Ligands". . p. 1177 - 1185. Retrieved 2015.
• 6、 Holmes, Aaron S.,Patrick, Brian O.,Levesque, Taleah M.,Legzdins, Peter. "Hemilability of the 1,2-Bis(dimethylphosphino)ethane (dmpe) Ligand in Cp?Mo(NO)(κ2-dmpe)". . p. 11299 - 11309. Retrieved 2017/09/25.