3-Methyl-1-cyclohexene

• CAS: 591-48-0
• Catalog Number: ACM591480
• Category: Main Products
• Molecular Weight: 96.17
• Molecular Formula: C7H12
• Boiling Point: 105 °C(lit.)

Case Study

3-Methyl-1-cyclohexene as a Diels-Alder Adduct for the Synthesis of Toluene from C5 Feedstocks

Kundu, Sabuj, et al. ACS Catalysis 3.8 (2013): 1768-1773.

3-Methyl-1-cyclohexene serves as a key cyclic intermediate in a catalytic route that converts C5 feedstocks to toluene, being formed through an in situ Diels-Alder reaction between 1,3-pentadiene and ethylene during iridium-catalyzed transfer dehydrogenation and subsequently dehydrogenated to the aromatic product.
Experimental Protocol: 1-Pentene is heated at 250 degrees Celsius with 600 psi ethylene in the presence of 0.3 mol% of a thermally stable anthraphos-based iridium pincer catalyst, allowing the intermediate to accumulate as the major product. Ethylene serves simultaneously as the hydrogen acceptor and the Diels-Alder trapping agent, and the catalyst tolerates prolonged heating up to 250 degrees Celsius. The isolated cycloalkene is then dehydrogenated either in solution at 180 degrees Celsius with tert-butylethylene as hydrogen acceptor and 0.19 mol% catalyst, or in the vapor phase over supported metal catalysts between 300 and 400 degrees Celsius with nitrogen as carrier gas.
Performance Evaluation: The Diels-Alder intermediate reaches 57.9% of the reaction mixture after 5.5 days. Homogeneous dehydrogenation delivers 98% toluene within 1 h, while vapor-phase conversion over supported platinum at 300 degrees Celsius gives quantitative conversion with 100% toluene and no side products. Supported palladium affords 92.3% toluene.

3-Methyl-1-cyclohexene as a Model Fuel for Investigating Soot Precursor Formation in Combustion

Kim, Seonah, et al. Proceedings of the Combustion Institute 37.1 (2019): 1083-1090.

3-Methyl-1-cyclohexene acts as a model hydrocarbon fuel in flow reactor experiments that probe the chemistry of soot precursor formation, preferentially undergoing dehydrogenation toward cyclic dienes and toluene rather than ring opening.
Experimental Protocol: The neat compound is fed into a quartz flow reactor at 10 uL/min with helium dilution, oxygen at stoichiometric air-to-fuel ratio, and argon tracer, over temperatures from 850 K to 1100 K in 25 K increments at a fixed residence time of 0.35 s. Reaction products are analyzed by two gas chromatographic systems, and competing pathways are evaluated by density functional theory calculations using composite methods. All three isomers share identical cetane numbers of 25 and 26, and a perfectly stirred reactor simulation at equivalence ratio 2 complements the experimental work.
Performance Evaluation: The compound displays a measured yield sooting index of 85.0, substantially above the values of 62.0 and 61.0 for its positional isomers, yet close to the predicted value of 77.9. It yields the highest concentrations of aromatics at all temperatures, while hydrogen abstraction by hydroxyl radicals shows barriers below 5 kcal/mol. The competing retro-Diels-Alder reaction requires 61 kcal/mol, consistent with the enhanced sooting tendency.

Custom Q&A

What is the molecular formula of 3-Methyl-1-cyclohexene?

The molecular formula of 3-Methyl-1-cyclohexene is C7H12.

What is the molecular weight of 3-Methyl-1-cyclohexene?

The molecular weight of 3-Methyl-1-cyclohexene is 96.17 g/mol.

What is the IUPAC name of 3-Methyl-1-cyclohexene?

The IUPAC name of 3-Methyl-1-cyclohexene is 3-methylcyclohexene.

What is the InChI of 3-Methyl-1-cyclohexene?

The InChI of 3-Methyl-1-cyclohexene is InChI=1S/C7H12/c1-7-5-3-2-4-6-7/h3,5,7H,2,4,6H2,1H3.

What is the InChIKey of 3-Methyl-1-cyclohexene?

The InChIKey of 3-Methyl-1-cyclohexene is UZPWKTCMUADILM-UHFFFAOYSA-N.

What is the CAS number of 3-Methyl-1-cyclohexene?

The CAS number of 3-Methyl-1-cyclohexene is 591-48-0.

What is the molecular weight of 3-Methyl-1-cyclohexene according to PubChem?

The molecular weight of 3-Methyl-1-cyclohexene according to PubChem is 96.17 g/mol.

How many hydrogen bond donor counts does 3-Methyl-1-cyclohexene have?

3-Methyl-1-cyclohexene has 0 hydrogen bond donor counts.

How many rotatable bond counts does 3-Methyl-1-cyclohexene have?

3-Methyl-1-cyclohexene has a rotatable bond count.

Is 3-Methyl-1-cyclohexene a canonicalized compound?

Yes, 3-Methyl-1-cyclohexene is a canonicalized compound according to PubChem.