Methylenecyclopentane

Base Information

• Chemical Name: Methylenecyclopentane
• CAS No.: 1528-30-9
• Molecular Formula: C6H10
• Molecular Weight: 82.1454
• Hs Code.: 2902199090
• European Community (EC) Number: 216-203-4
• DSSTox Substance ID: DTXSID9061756
• Nikkaji Number: J132.791G
• Wikidata: Q81989649
• Mol file: 1528-30-9.mol

Synonyms:Methylenecyclopentane;1528-30-9;Cyclopentane, methylene-;methylidenecyclopentane;EINECS 216-203-4;methylencyclopentane;methlenecyclopentane;methylene-cyclopentane;Methylene cyclopentane;Methylenecyclopentane, 97%;DTXSID9061756;MFCD00001421;AKOS009156906;FT-0608083;M0914;EN300-61006;D91403;J-008954

Chemical Property of Methylenecyclopentane

Chemical Property:

• Vapor Pressure: 115mmHg at 25°C
• Refractive Index: n20/D 1.435(lit.)
• Boiling Point: 75.5 °C at 760 mmHg
• Flash Point: -18 °C
• PSA: 0.00000
• Density: 0.79 g/cm³
• LogP: 2.11660
• Storage Temp.: 2-8°C
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 82.078250319
• Heavy Atom Count: 6
• Complexity: 54.4

Purity/Quality:

98%,99%, ^*data from raw suppliers

Methylenecyclopentane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F, Xi
• Hazard Codes: F,Xn
• Statements: 11-65
• Safety Statements: 16-62

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=C1CCCC1
• Uses: Methylenecyclopentane has been used in total synthesis of (±)-cephalotaxin.

Technology Process of Methylenecyclopentane

There total 80 articles about Methylenecyclopentane 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: 57.0%

6-chlorohexene (928-89-2) → 1-hexene (592-41-6,25067-06-5) + methylenecyclopentane (1528-30-9) + methyl-cyclopentane (96-37-7)

Guidance literature:

With Cp₂Zr(PMePh₂)2; diphenyl(methyl)phosphine; In benzene; for 0.75h; Ambient temperature;

DOI:10.1021/ja00530a076

Reference yield: 57.0%

1,5-Hexadien (592-42-7) → (E,Z)-2,4-hexadiene (5194-50-3) + (E)-1,4-hexadiene (7319-00-8) + methylenecyclopentane (1528-30-9) + 1-methylcyclopent-1-ene (693-89-0)

Guidance literature:

With isopropylmagnesium bromide; bis(cyclopentadienyl)titanium dichloride; In diethyl ether; at 20 ℃; for 3h; Further byproducts given. Yields of byproduct given;

Reference yield: 54.4%

cyclohexene (110-83-8) → methylenecyclopentane (1528-30-9) + 1-methylcyclopent-1-ene (693-89-0) + 3-methyl-1-cyclopentene (1120-62-3)

Guidance literature:

ultrastabilized Y zeolite; at 450 ℃; for 1h;

upstream raw materials:

1-cyclopentene-1-carboxaldehyde

1-cyclopentenylacetic acid

1,1-cyclopentanediacetic acid

cyclopent-1-enyl-acetonitrile

Downstream raw materials:

2-methyl-cyclopent-1-enecarboxylic acid

trans-3-Hexene

trans-2-hexene

methyl-cyclopentane

Refernces

• 1、 Arnold et al.. "-". . p. 2871. Retrieved 1950.
• 2、 McCarroll, Andrew J.,Walton, John C.. "Enhanced radical delivery from aldoxime esters for EPR and ring closure applications". . p. 351 - 352. Retrieved 2000.
• 3、 Redman, Eric W.,Morton, Thomas Hellman. "Product-Determining Steps in Gas-Phase Bronsted Acid-Base REactions. Deprotonation of 1-Methylcyclopentyl Cation by Amine Bases". . p. 5701 - 5708. Retrieved 1986.
• 4、 Gurbanov, Rustam,Sokolov, Andriy,Golovach, Sergey,Melnykov, Kostiantyn,Dobrydnev, Alexey V.,Grygorenko, Oleksandr O.. "Synthesis of sp 3-Enriched β-Fluoro Sulfonyl Chlorides". . p. 1771 - 1784. Retrieved 2020/12/28.
• 5、 Makume, Boitumelo F.,Holzapfel, Cedric W.,Maumela, Munaka C.,Willemse, J. Alexander,van den Berg, Jan A.. "Ethylene Tetramerisation: A Structure-Selectivity Correlation". . p. 2308 - 2315. Retrieved 2020/11/03.