1743-61-9

Usage

Uses

Used in Polymer and Resin Production:
1,4-dimethyl-4-vinylcyclohexene is used as a monomer in the polymer and resin industry for its ability to polymerize and form strong, durable materials. This property makes it suitable for creating various polymers and resins that are used in a wide range of applications, including coatings, adhesives, and composite materials.
Used in Adhesive Manufacturing:
In the adhesive manufacturing industry, 1,4-dimethyl-4-vinylcyclohexene is used as a key component to produce high-performance adhesives. Its polymerization capability contributes to the development of adhesives with enhanced bonding strength and durability.
Used as a Fragrance Intermediate:
1,4-dimethyl-4-vinylcyclohexene is utilized as a fragrance intermediate in the perfumery and cosmetics industry. Its sweet odor makes it a valuable ingredient in the creation of various fragrances and scented products.
Used in Specialty Chemicals and Pharmaceuticals:
In the specialty chemicals and pharmaceuticals industry, 1,4-dimethyl-4-vinylcyclohexene is employed as a building block for the synthesis of complex organic compounds. Its unique chemical structure allows it to be used in the development of novel specialty chemicals and pharmaceutical products.
Overall, 1,4-dimethyl-4-vinylcyclohexene's versatility and low toxicity make it a valuable compound in various industrial applications, from polymer and adhesive production to fragrances and pharmaceuticals. However, it is crucial to follow proper safety guidelines to minimize any potential risks associated with its use.

InChI:InChI=1/C10H16/c1-4-10(3)7-5-9(2)6-8-10/h4-5H,1,6-8H2,2-3H3

Upstream product

• 78-79-5 isoprene 
• 19465-00-0 trans-1,2-dimethyl-1,2-divinylcyclobutane 
• 14630-40-1 Bis(trimethylsilyl)ethyne 

Downstream Products

• 1123-35-9 4-ethyl-1,4-dimethyl-cyclohexene 
• 66338-39-4 1,4-dimethyl-4vinylcyclohexane-1-ol 

Relevant academic research and scientific papers

Application of molecular dynamics to chromatographic-spectral identification of isomeric products of organic reactions

Isomeric products of [2+4]-cycloaddition reactions can be identified by gas chromatography-mass spectrometry on the basis of their experimental retention parameters and intramolecular vibrational and rotational energies (E) calculated by molecular mechanics for all possible isomers. The Chromatographic parameters change in the opposite direction with respect to E. The proposed approach allows unambiguous identification of four products formed by each of the reactions of butadiene with cyclopentadiene, of isoprene with 2,3-dimethylbutadiene, of cyclopentadiene with isoprene, and dimerization of isoprene and two of the four products formed by the reaction of 1,3-cyclohexadiene with cyclopentadiene. Both structural and steric isomers (exo, endo) can be distinguished. 1998 MAHK "Hayka/Interperiodica".

TITANIUM-CATALYZED DIELS-ALDER CYCLOADDITION OF CONJUGATED DIENES TO BIS(TRIMETHYLSILYL)ACETYLENE. 1,2-BIS(TRIMETHYLSILYL)CYCLOHEXA-1,4-DIENE, 1,2-BIS(TRIMETHYLSILYL)BENZENE, AND THEIR METHYL DERIVATIVES

The catalytic system Et2AlCl/TiCl4 induces Diels-Alder cycloaddition of bis(trimethylsilyl)acetylene to 1,3-butadiene, isoprene, 2,3-dimethyl-1,3-butadiene and (E)-1,3-pentadiene affording 1,2-bis(trimethylsilyl)cyclohexa-1,4-dienes in high yields.The cyclohexadienes are readily converted to the corresponding 1,2-bis(trimethylsilyl)benzenes upon heating to 240 deg C.Mass, infrared, 1H, 13C and 29Si NMR spectra of all the products obtained are reported and briefly discussed.The crowded character of aromatic compounds is reflected in their mass, 13C and 29Si NMR spectra.

SPECIFIC ALLYLIC-ALLYLIC COUPLING PROCEDURES EFFECTED BY LIGAND-INDUCED ELIMINATION FROM DI(ALLYLIC)PALLADIUM SPECIES

Bis(allylic)palladium complexes can be induced to undergo reductive elimination by replacement of phosphine ligands in the system with ?-acidic ligands.The product 1,5-dienes, formed in high yield, are predominantly the 'head-to-head' coupled isomers.The bis(allylic)palladium intermediates may be formed by addition of an allylic Grignard or trialkyl(allylic)tin reagent to an(η3-allyl)palladium chloride complex, or by 1,3-diene condensation.The latter process leads to cyclodimerization, 'unusual' for palladium catalysed reactions.

TITANKOMPLEXE OFFENKETTIGER UND CYCLISCHER ARSANLIGANDEN: SYNTHESE UND KATALYTISCHE WIRKUNG (1)

The Ti(IV) complexes 1b, 2b, and 6 have been synthesized from new multi-electron ligands. 2b, after reduction with Et2AlCl, dimerizes isoprene mainly to 8c and trimerizes butadiene mainly to ttt-CDT.Ti(IV) compounds of the macrocyclic ligands 7a-c exhibit the same catalytic properties after reduction with Et2AlCl.

On the mechanism of the nickel-catalysed regioselective cyclodimerization of isoprene

A study of various Ni-ligand catalysed oligomerizations of isoprene has shown that with π-acidic P ligands the selectivity to cyclodimers amount to 97%. A new type of ligand is introduced, viz. fluoroalkyl phosphites having π-acceptor properties comparable to those of, e.g. PCl3. With tris(hexafluoroisopropyl) phosphite the main product is 1,4-dimethy1-4-vinylcyclohexene. A detailed explanation based on a two-step mechanism is given. As to the first step, for a series of ligands having similar steric properties the changes in product distribution as a function of the electronic ligand parameter are explained in terms of a gradual change in HOMO-LUMO interactions between Ni and the olefins, with strong π-acidic ligands promoting the head-to-head coupling of the isoprene molecules. The second step, involving reductive elimination of a cyclodimer from the metal, shows an increasing selectivity towards substituted cyclohexenes for the head-to-head and tail-to-tail intermediates with increasing π-acidity of the ligand. The qualitative orbital treatment presented as an explanation is also applicable to reactions found for other metallacyclopentanes.