514-94-3

Basic information

• Product Name: 1,5,5,6-tetramethylcyclohexa-1,3-diene
• Synonyms: 1,5,5,6-tetramethylcyclohexa-1,3-diene;1,5,5,6-Tetramethyl-1,3-cyclohexadiene
• CAS NO: 514-94-3
• Molecular Formula: C₁₀H₁₆
• Molecular Weight: 136.23
• Mol File: 514-94-3.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 160°Cat760mmHg
• Flash Point: 37.7°C
• Appearance: /
• Density: 0.804g/cm³
• Vapor Pressure: 3.16mmHg at 25°C
• Refractive Index: 1.45
• CAS DataBase Reference: 1,5,5,6-tetramethylcyclohexa-1,3-diene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,5,5,6-tetramethylcyclohexa-1,3-diene(514-94-3)
• EPA Substance Registry System: 1,5,5,6-tetramethylcyclohexa-1,3-diene(514-94-3)

Safety Data

• Hazardous Substances Data: 514-94-3(Hazardous Substances Data)

Usage

Physical state

Colorless liquid

Odor

Strong aromatic

Uses

a. Fragrance ingredient in perfumes and cosmetic products
b. Production of industrial products (adhesives, sealants, and coatings)

Flammability

Highly flammable

Safety precautions

a. Handle with caution
b. Potential for skin, eye, and respiratory irritation
c. Proper safety measures should be taken when working with this chemical

InChI:InChI=1/C10H16/c1-8-6-5-7-10(3,4)9(8)2/h5-7,9H,1-4H3

Upstream product

• 7785-70-8 (+)-α-pinene 
• 3016-19-1 (E,E)-2,6-dimethyl-2,4,6-octatriene 
• 80-56-8 Pinene 
• 5989-27-5 D-limonene 
• 7785-26-4 (-)-α-pinene 

Downstream Products

• 55196-00-4 4,5,5-trimethyl-3-methylene-1-cyclohexene 
• 513-35-9 2-methyl-but-2-ene 
• 21483-46-5 dimethyl 3-methylbenzene-1,2-dicarboxylate 
• 74-84-0 ethane 
• 108-38-3 m-xylene 

Relevant articles and documents

Kinetics of thermal conversions of monoterpenic compounds in supercritical lower alcohols

The most important information concerning thermal conversions of vegetable terpenes (α-pinene, β-pinene, turpentine, and cis-verbenol) in supercritical lower alcohols is systematized. The kinetics of selected reactions is reported and is compared with the kinetics of the same reactions in the gas and liquid phases. Thermodynamic calculations of the phase states and kinetic parameters are presented for a number of multicomponent multiphase systems containing terpenes and lower alcohols. The effect of the supercritical solvent pressure on the rate and selectivity of the selected reactions is reported.

Comprehensive kinetic and mechanistic considerations for the gas-phase behaviour of pinane-type compounds

The thermal behaviour of selected pinane-type compounds, α-pinene (1), β-pinene (2), pinane (3) and nopinone (4), has been investigated. The conversion of the bicyclic starting materials to their acyclic and monocyclic isomers as well as the consecutive reactions of the acyclic main isomerisation products are discussed. The conversion of 1-4 in a reaction network is presented and the experimental evidence for the formation of pyrolysis products by a biradical pathway is discussed. In addition to these results a kinetic model describing the isomerisation of the bicyclic compounds to their acyclic and monocyclic isomers is presented. A good correlation between kinetic simulations and experimental data is revealed. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

The kinetics, stereochemistry, and deuterium isotope effects in the α-pinene pyrolysis. Evidence for incursion of multiple conformations of a diradical

Pyrolysis of optically active α-pinene gave 95% racemic limonene (dipentene), alloocimine, racemic α-pinene, α-pyronene. Activation parameters are reported. Pyrolysis of (S) syn-6-trideuteriomethyl α-pinene at 256.7°C for 2400s gave dipentene with twice as much deuterium as hydrogen transfer with kH/kD=1.49 and alloocimine with a Z and E trideuteriomethyl ratio of ca. 5 with kH/kD=0.89. The isotope effect on loss of starting material was 1.16. Separation of the enantiomers of α-pinene from 3600s pyrolyses at 256.7°C followed by NMR analysis revealed that the ratio of the R-syn to R-anti to S-anti isomers is 4.6:3.7:1 at roughly two half-lives. Kinetic analysis reveals that the previously proposed mechanism for all conversions involving slow interconversion of two diradicals with Cs symmetry is not consistent with the distribution of the ??-pinene isomers, particularly the formation of more suprafacial-retention product (R-anti) than bond-rotated isomer (S-anti). Inclusion of another Cs species (ignoring the deuteriums) that would be intermediate between the originally proposed Cs species, appears more consistent with the observations.