5698-48-6

Basic information

• Product Name: Undecane, 5-methylene-
• Synonyms: Undecane, 5-methylene-;2-Butyl-1-octene
• CAS NO: 5698-48-6
• Molecular Formula: C₁₂H₂₄
• Molecular Weight: 168.32
• Mol File: 5698-48-6.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 209.5°C at 760 mmHg
• Flash Point: 72.2°C
• Appearance: /
• Density: 0.759g/cm³
• Vapor Pressure: 0.292mmHg at 25°C
• Refractive Index: 1.429
• CAS DataBase Reference: Undecane, 5-methylene-(CAS DataBase Reference)
• NIST Chemistry Reference: Undecane, 5-methylene-(5698-48-6)
• EPA Substance Registry System: Undecane, 5-methylene-(5698-48-6)

Safety Data

• Hazardous Substances Data: 5698-48-6(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 43, p. 147, 1978 DOI: 10.1021/jo00395a033Tetrahedron Letters, 21, p. 945, 1980

InChI:InChI=1/C12H24/c1-4-6-8-9-11-12(3)10-7-5-2/h3-11H2,1-2H3

Upstream product

• 592-41-6 1-hexene 
• 187737-37-7 propene 
• 111-66-0 oct-1-ene 
• 75-24-1 trimethylaluminum 
• 142-82-5 n-heptane 
• 3913-02-8 2-(n-butyl)octanol 
• 112-53-8 1-dodecyl alcohol 

Downstream Products

• 33083-83-9 undecan-5-one 
• 3913-02-8 2-(n-butyl)octanol 
• 78426-37-6 (2-butyloctyl)ethylaluminum chloride 
• 74-85-1 ethene 

Relevant articles and documents

Structurally uniform 1-hexene, 1-octene, and 1-decene oligomers: Zirconocene/MAO-catalyzed preparation, characterization, and prospects of their use as low-viscosity low-temperature oil base stocks

An original approach to α-olefin oligomerization as well as novel thermally stable zirconocene catalysts for use in such reactions has been elaborated. The method reported allows the achievement of fractions of lightweight α-olefin oligomers up to 90% yields without considerable formation of byproducts like internal alkenes, alkanes, and higher oligomers. Trimers, tetramers, and pentamers of 1-hexene, 1-octene, and 1-decene were isolated as individual compounds and were hydrogenated. Viscosity characteristics of the isolated saturated and unsaturated hydrocarbons have been studied at various temperatures. The isolated saturated oligomers of 1-octene and 1-decene outperform the traditional electrophilic oligomerization products in terms of viscosity indexes, pour points, and low-temperature viscosity.

Highly Efficient and 1,2-Regioselective Method for the Oligomerization of 1-Hexene Promoted by Zirconium Precatalysts with [OSSO]-Type Bis(phenolate) Ligands

A mixture of zirconium complex 7, which carries a phenyl-substituted [OSSO]-type bis(phenolate) ligand, and dried modified methylaluminoxane (dMMAO) catalyzes the 1,2-regioselective oligomerization of 1-hexene at relatively low catalyst loadings (0.0056 mol %) to produce the corresponding vinylidene-terminated dimer, 5-methyleneundecane (74-80%), and trimer, 7-butyl-5-methylenetridecane (8-11%). The observed turnover frequencies (TOFs) are relatively high (up to 11a€?100 h-1). When a mixture of 2,6-dimethylphenyl-substituted precatalyst 8 and dMMAO was used, the oligomerization of 1-hexene proceeded effectively to afford predominantly the dimer (87-91%) together with a small amount of the trimer (8-11%) at remarkably high TOFs (up to 6640 h-1).

Catalytic oligomerization of α-olefins in the presence of two-stage activated zirconocene catalyst based on 6,6-dimethylfulvene ‘dimer’

Zirconocene obtained from 6,6-dimethylfulvene ‘dimer’, being activated subsequently with triisobutylaluminium and methylalumoxane, catalyzes transformation of α-olefins into a mixture of vinylidene oligomers with minimal losses to isomerization, which allows one to consider this catalyst perspective for the synthesis of branched hydrocarbons with uniform structure.