1-Isopropyl-4-methylcyclohexane
[CAS# 99-82-1]

Identification

• Classification: Chemical reagent >> Organic reagent >> Alkane
• Name: 1-Isopropyl-4-methylcyclohexane
• Synonyms: 1-Methyl-4-isopropylcyclohexane; 4-Methyl-1-(1-methylethyl)cyclohexane; Woody River 10
• Molecular Formula: C₁₀H₂₀
• Molecular Weight: 140.27
• CAS Registry Number: 99-82-1
• EC Number: 202-790-4
• SMILES: CC1CCC(CC1)C(C)C

Properties

• Solubility: Insoluble (6.6E^-4 g/L) (25 ºC), Calc.^*
• Density: 0.785±0.06 g/cm³ (20 ºC 760 Torr), Calc.^*
• Melting point: -87.6 ºC^**
• Boiling point: 171.0-171.7 ºC^***
• Refractive index: 1.45562 (589.3 nm 22 ºC)^****
• Flash point: 44.7±11.7 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2014 ACD/Labs)

^** "PhysProp" data were obtained from Syracuse Research Corporation of Syracuse, New York (US)

^*** Kobe, Kenneth A.; Industrial and Engineering Chemistry 1940, V32, P775-7.

^**** Roenisch, Paul; Diss. Schlesische Friedrich-Wilhelms-Universitat, Breslau 1916, P69 pp..

Safety Data

• Hazard Symbols: GHS02;GHS07;GHS08 DangerGHS02
• Hazard Statements: H226-H304-H315
• Precautionary Statements: P210-P233-P240-P241-P242-P243-P264-P280-P301+P316-P302+P352-P303+P361+P353-P321-P331-P332+P317-P362+P364-P370+P378-P403+P235-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Flammable liquids	Flam. Liq.	3	H226
Aspiration hazard	Asp. Tox.	1	H304
Skin irritation	Skin Irrit.	2	H315
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400

Discovory and Applicatios

1-Isopropyl-4-methylcyclohexane is a saturated cycloalkane derivative with the molecular formula C₁₀H₂₀. Structurally, it consists of a cyclohexane ring substituted at the first carbon with an isopropyl group (–CH(CH₃)₂) and at the fourth carbon with a methyl group (–CH₃). This compound is one of many alkyl-substituted cyclohexanes studied for their conformational properties and applications in organic synthesis and industry.

The compound has been synthesized and characterized in various organic chemistry contexts, particularly as a model compound to understand steric effects and conformational preferences in substituted cyclohexanes. The substitution pattern at carbons 1 and 4 allows for examination of cis and trans isomers, which differ in the relative spatial orientation of the substituents on the cyclohexane ring, influencing the compound’s physical and chemical properties.

1-Isopropyl-4-methylcyclohexane can be prepared through alkylation reactions starting from cyclohexane or substituted cyclohexanes using appropriate alkyl halides under Friedel–Crafts alkylation or other catalytic conditions. Alternatively, it can be obtained by synthetic sequences involving selective substitution of functionalized cyclohexane intermediates.

This compound is mainly of interest in the fields of stereochemistry and conformational analysis because the isopropyl and methyl groups are bulky substituents that influence the ring’s preferred chair conformation. Generally, bulky groups prefer the equatorial position to minimize steric hindrance, affecting the overall stability and reactivity of the molecule.

In industrial or applied chemistry, derivatives of alkylcyclohexanes like 1-isopropyl-4-methylcyclohexane serve as intermediates or model compounds in the synthesis of fragrances, lubricants, and specialty chemicals. Their hydrophobic and relatively non-polar character makes them components or solvents in formulations where such properties are required.

Analytical techniques such as nuclear magnetic resonance (NMR) spectroscopy are employed to determine the stereochemistry and conformational preferences of 1-isopropyl-4-methylcyclohexane. Proton NMR and carbon-13 NMR provide detailed information about the chemical environment of the hydrogen and carbon atoms, including coupling constants that help distinguish between axial and equatorial substituents. Gas chromatography–mass spectrometry (GC-MS) is used for purity analysis and identification.

Physical properties such as boiling point, melting point, and density have been measured to aid in the characterization and industrial application of the compound. It is typically a colorless liquid at room temperature and shows low polarity consistent with its hydrocarbon structure.

Safety considerations for handling 1-isopropyl-4-methylcyclohexane include its flammability and potential for skin or respiratory irritation upon exposure. Standard laboratory safety practices such as working in a well-ventilated area and using personal protective equipment are recommended.

In summary, 1-isopropyl-4-methylcyclohexane is a substituted cycloalkane with significance in stereochemical studies and potential applications as a chemical intermediate in industry. Its conformational properties, synthesis, and characterization have been well documented, making it a useful compound in both academic and applied chemistry contexts.

References

2023. Thioterpenoids of the Bornane Series with Potent Activity Against Opportunistic Micromycetes. BioNanoScience, 13(1).
DOI: 10.1007/s12668-023-01069-2

2023. Terpenoids in resinites from middle Cretaceous karst infillings in the Rhenish Massif (Rhineland, Germany): botanical source and preservation. International Journal of Earth Sciences, 112(8).
DOI: 10.1007/s00531-023-02351-0

2024. Synthesis and antimicrobial activity of new thiomonoterpene carboxylic acids. Russian Chemical Bulletin, 73(2).
DOI: 10.1007/s11172-024-4152-7