99-85-4

Basic information

• Product Name: 4-Isopropyl-1-methyl-1,4-cyclohexadiene
• Synonyms: p-Mentha-1,4-diene(8CI);1-Isopropyl-4-methyl-1,4-cyclohexadiene;1-Methyl-4-(1-methylethyl)-1,4-cyclohexadiene;1-Methyl-4-isopropyl-1,4-cyclohexadiene;Crithmene;Moslene;NSC 21448;g-Terpinen;g-Terpinene;p-Mentha-1,4-diene
• CAS NO: 99-85-4
• Molecular Formula: C₁₀H₁₆
• Molecular Weight: 136.23
• EINECS: 202-794-6
• Mol File: 99-85-4.mol
• Article Data: 57

Chemical Properties

• Melting Point: -10 °C
• Boiling Point: 183 °C at 760 mmHg
• Flash Point: 51.7 °C
• Appearance: colourless oily liquid
• Density: 0.845 g/cm³
• Refractive Index: 1.474
• CAS DataBase Reference: 4-Isopropyl-1-methyl-1,4-cyclohexadiene(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Isopropyl-1-methyl-1,4-cyclohexadiene(99-85-4)
• EPA Substance Registry System: 4-Isopropyl-1-methyl-1,4-cyclohexadiene(99-85-4)

Safety Data

• Hazard Codes: Xi:Irritant
• Statements: R10:; R36/37/38:
• Safety Statements: S26:; S36:
• Hazardous Substances Data: 99-85-4(Hazardous Substances Data)

Usage

General Description

4-Isopropyl-1-methyl-1,4-cyclohexadiene is a chemical compound with the molecular formula C10H16. It is a colorless, flammable liquid with a strong, unpleasant odor. 4-Isopropyl-1-methyl-1,4-cyclohexadiene is used primarily as a chemical intermediate in the production of various other substances, including pharmaceuticals, pesticides, and fragrances. It is also used in the synthesis of organic compounds and as a solvent in certain industrial processes. Due to its potential flammability and toxicity, proper precautions must be taken when handling and storing 4-isopropyl-1-methyl-1,4-cyclohexadiene.

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

Upstream product

• 498-15-7 (+)-Δ³-carene 
• 69-72-7 salicylic acid 
• 1195-32-0 1-methyl-4-isopropenylbenzene 
• 99-87-6 4-methylisopropylbenzene 
• 562-74-3 TERPINEN-4-OL 
• 98-55-5 terpineol 
• 555-10-2 beta-phellandrene 
• 80-53-5 terpin hydrate 
• 5989-27-5 D-limonene 
• 127-91-3 (1R,5R)-(+)-β-pinene 
• 201230-82-2 carbon monoxide 
• 5113-87-1 3-methyl-6-(prop-1-en-2-yl)cyclohexene 
• 470-82-6 1,8-Cineole 
• 86119-84-8 phosphoric acid 

Downstream Products

• 99-86-5 1-methyl-4-isopropyl-1,3-cyclohexadiene 
• 99-87-6 4-methylisopropylbenzene 
• 536-66-3 p-isopropylbenzoic acid 
• 17023-75-5 4,5-Epoxy-4-isopropyl-1-methyl-1-cyclohexene 
• 17023-74-4 4,5-Epoxy-1-isopropyl-4-methyl-1-cyclohexene 
• 121079-02-5 (1α,3α,4β)-4,4'-<1-Methyl-4-(1-methylethyl)-1,3-cyclohexanediyl>bisphenol 
• 17023-73-3 (1,2 and 4,5)-diepoxy-1-isopropyl-4-methylcyclohexane 
• 17023-75-5 4,5-epoxy-p-menth-1-ene 
• 17023-74-4 terpinene monoxide 
• 99-82-1 Menthane 
• 25570-95-0 1,4-dichloro-trans-p-menthane 

Relevant articles and documents

Thioderivatives of Resorcin[4]arene and Pyrogallol[4]arene: Are Thiols Tolerated in the Self-Assembly Process?

Three novel thiol bearing resorcin[4]arene and pyrogallol[4]arene derivatives were synthesized. Their properties were studied with regards to self-assembly, disulfide chemistry, and Br?nsted acid catalysis. This work demonstrates that (1) one aromatic thiol on the resorcin[4]arene framework is tolerated in the self-assembly process to a hexameric hydrogen bond-based capsule, (2) thio-derivatized resorcin[4]arene analogs can be covalently linked through disulfides, and (3) the increased acidity of aromatic thio-substituent is not sufficient to replace HCl as cocatalyst for capsule catalyzed terpene cyclizations.

Transition metal triflate catalyzed conversion of alcohols, ethers and esters to olefins

Herein, we report an efficient transition metal triflate catalyzed approach to convert biomass-based compounds, such as monoterpene alcohols, sugar alcohols, octyl acetate and tea tree oil, to their corresponding olefins in high yields. The reaction proceeds through C-O bond cleavage under solvent-free conditions, where the catalytic activity is determined by the oxophilicity and the Lewis acidity of the metal catalyst. In addition, we demonstrate how the oxygen containing functionality affects the formation of the olefins. Furthermore, the robustness of the used metal triflate catalysts, Fe(OTf)3 and Hf(OTf)4, is highlighted by their ability to convert an over 2400-fold excess of 2-octanol to octenes in high isolated yields.

Terpene Cyclizations inside a Supramolecular Catalyst: Leaving-Group-Controlled Product Selectivity and Mechanistic Studies

The tail-to-head terpene cyclization is arguably one of the most complex reactions found in nature. The hydrogen-bond-based resorcinarene capsule represents the first man-made enzyme-like catalyst that is capable of catalyzing this reaction. Based on noncovalent interactions between the capsule and the substrate, the product selectivity can be tuned by using different leaving groups. A detailed mechanistic investigation was performed to elucidate the reaction mechanism. For the cyclization of geranyl acetate, it was found that the cleavage of the leaving group is the rate-determining step. Furthermore, the studies revealed that trace amounts of acid are required as cocatalyst. A series of control experiments demonstrate that a synergistic interplay between the supramolecular capsule and the acid traces is required for catalytic activity.