trans-4-Methylcyclohexyl amine
[CAS# 2523-55-9]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Amine
• Name: trans-4-Methylcyclohexyl amine
• Synonyms: 4-methylcyclohexan-1-amine
• Molecular Formula: C₇H₁₅N
• Molecular Weight: 113.20
• CAS Registry Number: 2523-55-9
• EC Number: 607-658-3
• SMILES: CC1CCC(CC1)N

Properties

• Density: 0.8±0.1 g/cm³, Calc.^*, 0.85 g/mL (Expl.)
• Index of Refraction: 1.449, Calc.^*
• Boiling Point: 149.3±8.0 °C (760 mmHg), Calc.^*, 151-154 °C (Expl.)
• Flash Point: 26.7±0.0 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS02;GHS05 Danger
• Risk Statements: H226-H314
• Safety Statements: P210-P233-P240-P241-P242-P243-P260-P264-P280-P301+P330+P331-P302+P361+P354-P303+P361+P353-P304+P340-P305+P354+P338-P316-P321-P363-P370+P378-P403+P235-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Flammable liquids	Flam. Liq.	3	H226
Skin corrosion	Skin Corr.	1B	H314
Serious eye damage	Eye Dam.	1	H318

Discovery and Applications

trans-4-Methylcyclohexyl amine is a cyclic amine with the molecular formula C7H15N, belonging to the family of substituted cyclohexyl amines. It is characterized by a methyl substituent in the para (trans) position on the cyclohexane ring relative to the amine group. This compound exists as a stereoisomer, with the trans-configuration contributing to its specific chemical and physical properties. It is a colorless to pale yellow liquid with an ammonia-like odor and serves as a versatile intermediate in various industrial and chemical applications.

The discovery of trans-4-methylcyclohexyl amine can be traced to research efforts aimed at synthesizing functionalized amines for use in industrial processes. Its synthesis typically involves hydrogenation reactions of aromatic precursors such as p-toluidine under conditions that favor selective formation of the trans isomer. Advances in catalytic hydrogenation methods have allowed for the efficient and cost-effective production of this compound, ensuring its availability for industrial-scale applications.

A significant application of trans-4-methylcyclohexyl amine lies in the production of polyamide and polyurethane materials. As a curing agent or hardener, it facilitates the cross-linking of epoxy resins, enhancing the mechanical and thermal properties of the resulting polymers. These materials find extensive use in coatings, adhesives, and composite materials, particularly in automotive and aerospace industries.

In the field of organic synthesis, trans-4-methylcyclohexyl amine serves as a valuable building block for the preparation of agrochemicals, pharmaceuticals, and dyes. Its unique stereochemistry and reactivity profile make it a suitable precursor for designing complex molecules. Additionally, the compound is investigated for its potential as a corrosion inhibitor in industrial systems, where it helps protect metal surfaces from oxidative degradation.

Safety considerations are crucial in handling trans-4-methylcyclohexyl amine due to its potential irritant and toxic effects. Appropriate safety measures, such as the use of personal protective equipment and proper ventilation, are recommended during its use in industrial and laboratory settings.

The versatility and functional importance of trans-4-methylcyclohexyl amine continue to drive research into its applications. Innovations in its synthesis and utilization contribute to its growing relevance in material science and specialty chemical industries.

References

2022. Oxidative coupling of dibenzyl disulfide with amines catalyzed by quinoline-bromine complex: access to thioamides. *Molecular Diversity*, 26(3).
DOI: 10.1007/s11030-022-10403-x

2010. Stereoselective Synthesis of Alicyclic Amines. *Topics in Catalysis*, 53(7-8).
DOI: 10.1007/s11244-010-9544-2

2005. Control of Spermidine and Spermine Levels in Rat Tissues by trans-4-Methylcyclohexylamine, a Spermidine-Synthase Inhibitor. *Biological and Pharmaceutical Bulletin*, 28(4).
DOI: 10.1248/bpb.28.569