5-Ethenyl-1,2,3,4,5-pentamethylcyclopenta-1,3-diene

Base Information

• Chemical Name: 5-Ethenyl-1,2,3,4,5-pentamethylcyclopenta-1,3-diene
• CAS No.: 20145-47-5
• Molecular Formula: C12H18
• Molecular Weight: 162.2713
• NSC Number: 157460
• DSSTox Substance ID: DTXSID90303234
• Nikkaji Number: J926.778F
• Mol file: 20145-47-5.mol

Synonyms:20145-47-5;5-ethenyl-1,2,3,4,5-pentamethylcyclopenta-1,3-diene;NSC157460;1,2,3,4,5-Pentamethyl-5-vinyl-1,3-cyclopentadiene;DTXSID90303234;NSC-157460;5-vinyl-1,2,3,4,5-penta-methylcyclopentadiene

Chemical Property of 5-Ethenyl-1,2,3,4,5-pentamethylcyclopenta-1,3-diene

Chemical Property:

• Vapor Pressure: 0.744mmHg at 25°C
• Boiling Point: 190.6°Cat760mmHg
• Flash Point: 58.7°C
• Density: 0.869g/cm³
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 162.140850574
• Heavy Atom Count: 12
• Complexity: 263

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=C(C(C(=C1C)C)(C)C=C)C

Technology Process of 5-Ethenyl-1,2,3,4,5-pentamethylcyclopenta-1,3-diene

There total 7 articles about 5-Ethenyl-1,2,3,4,5-pentamethylcyclopenta-1,3-diene 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%

5-(1-chloroethyl)-1,2,3,4,5-pentamethyl-1,3-cyclopentadiene (19835-61-1) → 1,2,3,4,5-pentamethyl-5-vinyl-1,3-cyclopentadiene (20145-47-5)

Guidance literature:

With potassium tert-butylate; In diethyl ether; dimethyl sulfoxide; at 25 ℃; for 12h;

DOI:10.1002/hlca.19840670805

Reference yield:

1,2,3,4,6-pentamethylfulvene (122427-60-5) + methyl iodide (74-88-4) → 1,2,4,5,5-pentamethyl-3-vinyl-cyclopenta-1,3-diene + 1,2,3,5,5-pentamethyl-4-vinyl-cyclopenta-1,3-diene + 1,2,3,4,5-pentamethyl-5-vinyl-1,3-cyclopentadiene (20145-47-5)

Guidance literature:

1,2,3,4,6-pentamethylfulvene; With lithium diisopropyl amide; In tetrahydrofuran;

methyl iodide; In tetrahydrofuran; at -20 ℃; Title compound not separated from byproducts;

DOI:10.1007/s11172-005-0263-y

Reference yield:

5-acetyl-1,2,3,4,5-pentamethylcyclopentadiene (15971-76-3) → 1,2,3,4,5-pentamethyl-5-vinyl-1,3-cyclopentadiene (20145-47-5)

Guidance literature:

Multi-step reaction with 4 steps

1: NaBH₄ / methanol

2: 60 percent / Et₃NSO₂NCO₂CH₃ / tetrahydrofuran / 0.75 h / Heating

3: 95 percent / HCl / CH₂Cl₂

4: 92 percent / t-BuOK / dimethylsulfoxide; diethyl ether / 12 h / 25 °C

With hydrogenchloride; sodium tetrahydroborate; Burgess Reagent; potassium tert-butylate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; dimethyl sulfoxide;

DOI:10.1002/hlca.19840670805

upstream raw materials:

1,2,3,5,6-exo-Pentamethyl-4-methylenbicyclo<3.1.0>hex-2-en

5-(1-chloroethyl)-1,2,3,4,5-pentamethyl-1,3-cyclopentadiene

1,2,3,4,6-pentamethylfulvene

methyl iodide