cis-4-Methylcyclohexylamine, CAS number 2523-56-0
- Molecular Formula: C7H15N
- Molecular Weight: 113.201
- Physical State: Clear to pale yellow liquid
- Density: 0.844
- Boiling Point: 154°C
- Melting Point: ~-8.5°C
- Refractive Index: 1.4550 to 1.4590
- Solubility: Soluble in chloroform, dichloromethane, and ethyl acetate
- pKa: 10.58
- Transport Classification: Hazardous material (UN 2734 8/3/PG II)
- Storage Conditions: Short-term at -4°C; long-term at -20°C
- Purity: Up to 98%
- Applications: Used as an intermediate in chemical reactions, including the synthesis of derivatives like cis-4-Methylcyclohexylamine hydrochloride.
- Synthesis Method:
- Starting material: 4-methylphenylboronic acid/ester
- Hydrogenation under rhodium-carbon catalyst yields a cis-trans mixture
- Recrystallization to obtain cis-4-methylcyclohexylboronic acid/ester
- Aminosulfonic acid and alkaline solution for amine substitution to obtain cis-4-methylcyclohexylamine
- Reaction yield: High, with purity >99.5%
- Catalyst can be reused 7 times
- Mass production achieved
References
The application of low temperature 13C nuclear magnetic resonance spectroscopy to the determination of the A values of amino-, methylamino-, and dimethylamino-substituents in cyclohexane
Journal of the Chemical Society, Perkin Transactions 2, Issue 8, 1976 DOI: 10.1039/P29760000895
The variable temperature 13C spectra of cis-4-methylcyclohexylamine, cis-4,N-dimethylcyclohexylamine, and cis-4,NN-trimethylcyclohexylamine have been measured and interpreted, yielding 13C chemical shift parameters for conformations with equatorial and axial NH2, NHMe, and NMe2 groups attached to cyclohexane.
Analyse conformationnelle par resonance nucleaire magnetique—V : Grandeurs thermodynamiques regissant l'equilibre conformationnel de la cyclohexylamine
Tetrahedron, Volume 24, Issue 9, 1968, Pages 3647-3654 DOI: 10.1016/S0040-4020(01)91997-0
Thermodynamic data (ΔG°, ΔH° and ΔS°) of an amino group attached to a cyclohexane ring have been obtained, using a modification of Eliel's method, based on variable temperature NMR. a discrepancy was observed between the data concerning cyclohexylamine itself (“direct” method), and that obtained via cis-4-methylcyclohexylamine “direct]rd method, based on the assumption of additivity of the thermodynamic parameters of amino and methyl groups).