4724-89-4

Basic information

• Product Name: 1,3,5,5-TETRAMETHYL-1,3-CYCLOHEXADIENE
• Synonyms: 1,3,5,5-TETRAMETHYL-1,3-CYCLOHEXADIENE;1,3,5,5-tetramethyl-3-cyclohexadiene;11,3,5,5-TETRAMETHYL-1,3-CYCLOHEXADIENE;1,3,5,5-tetramethylcyclohexa-1,3-diene
• CAS NO: 4724-89-4
• Molecular Formula: C₁₀H₁₆
• Molecular Weight: 136.23
• Mol File: 4724-89-4.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 162.3°Cat760mmHg
• Flash Point: 52 °C
• Appearance: /
• Density: 0.82
• Vapor Pressure: 2.85mmHg at 25°C
• Refractive Index: 1.4650
• CAS DataBase Reference: 1,3,5,5-TETRAMETHYL-1,3-CYCLOHEXADIENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,5,5-TETRAMETHYL-1,3-CYCLOHEXADIENE(4724-89-4)
• EPA Substance Registry System: 1,3,5,5-TETRAMETHYL-1,3-CYCLOHEXADIENE(4724-89-4)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• RIDADR: UN3295
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 4724-89-4(Hazardous Substances Data)

Usage

General Description

1,3,5,5-Tetramethyl-1,3-cyclohexadiene, also known as TMCH, is a chemical compound with the molecular formula C10H16. It is a colorless liquid that is highly flammable and insoluble in water. TMCH is primarily used as a reactant in organic synthesis, particularly in the production of pharmaceuticals, fragrances, and other fine chemicals. It is also used as a flavoring agent and a precursor in the manufacturing of dyes and pigments. TMCH is known for its high reactivity and is typically handled with care due to its potential hazards, including its flammability and ability to cause irritation upon contact with skin or eyes.

InChI:InChI=1/C10H16/c1-8-5-9(2)7-10(3,4)6-8/h5-6H,7H2,1-4H3

Upstream product

• 78-59-1 3,5,5-Trimethylcyclohex-2-en-1-one 
• 75-16-1 methylmagnesium bromide 
• 2352-55-8 2,4,6-trimethyl-2,5-heptadien-1-ol 
• 94925-94-7 3-Hydroxy-1,3,5,5-Tetramethylcyclohexen 
• 74-88-4 methyl iodide 
• 80-56-8 Pinene 
• 676-58-4 methylmagnesium chloride 
• 917-54-4 methyllithium 

Downstream Products

• 108-67-8 1,3,5-trimethyl-benzene 
• 50966-95-5 1,3,3,5,5-pentamethyl-cyclohexene 
• 927-03-7 (Z)-2,4,6-trimethyl-hepta-1,3,5-triene 
• 927-04-8 (E)-2,4,6-trimethyl-hepta-1,3,5-triene 
• 41797-81-3 Z-2,4,6-Trimethyl-1,3,6-heptatrien 
• 41797-82-4 E-2,4,6-Trimethyl-1,3,6-heptatrien 
• 24770-67-0 neramexane 
• 106038-49-7 1,3,3,5,5-Pentamethyl-1-ethyl-cyclohexan 
• 100962-16-1 1,3,3,5,5-Pentamethyl-1-isopropyl-cyclohexan 

Relevant articles and documents

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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.

Cycloadditions of 1-(4-Methoxyphenyl)-2-methylvinyl Cation to Olefins. Stereochemistry and Structure of the Reaction Products

(E)-1-Bromo-1-(4-methoxyphenyl)-1-propene (1a) reacts stereospecifically with (Z)-2-butene and silver tetrafluoroborate by cycloaddition of the intermediate vinyl cation 2a to give cis-1-(4-methoxyphenyl)-2,3,4-trimethyl-1-cyclobutene (3); with (E)-2-butene, 3 and trans-1-(4-methoxyphenyl)-2,3,4-trimethyl-1-cyclobutene (4) are formed in a ratio of 1:4.These results are in accord with a synchronous cycloaddition of the vinyl cation 2a to (Z)- and (E)-2-butene.Cyclohexene derivatives 14a, 14b, and 14c are obtained predominantly by the reaction of 1a and AgBF4 or AgSbF6 with vinylcyclopropane (11), ethyl vinyl ether (12), and isobutene (13), respectively.