Overview
(S)-1-Cyclohexylethylamine is an optically active amine with a stereogenic center adjacent to the amino group. As a chiral auxiliary, it plays a critical role in asymmetric synthesis, particularly in pharmaceutical manufacturing where enantiomeric purity is essential. The compound's cyclohexyl ring provides steric bulk that influences stereoselectivity in reactions. The industrial production typically involves resolution of racemic mixtures or asymmetric hydrogenation methods. Its importance has grown with the increasing demand for single-enantiomer drugs, making it a valuable intermediate in fine chemical supply chains.
Physical and Chemical Properties
This secondary amine exhibits typical alkaline characteristics, forming stable salts with acids. The cyclohexyl group confers lipophilicity (logP ~2.1), affecting its solubility profile and making it more compatible with organic solvents than aqueous systems. Its optical rotation ([α]D20) typically ranges between +15° to +20° in methanol. Thermal stability allows its use in reactions up to 150°C, though it gradually oxidizes upon prolonged air exposure. The compound shows characteristic IR absorption at ~3350 cm−1 (N-H stretch) and 1100-1200 cm−1 (C-N stretch), useful for quality verification.
Main Applications
Primarily employed as a chiral resolving agent, (S)-1-cyclohexylethylamine facilitates the separation of racemic carboxylic acids through diastereomeric salt formation. In medicinal chemistry, it serves as a building block for beta-amino acid derivatives used in protease inhibitors and neurological drugs. The compound also functions as a ligand in transition metal catalysis for asymmetric hydrogenations. Recent applications include its use in synthesizing chiral ionic liquids for green chemistry processes. Pharmaceutical companies particularly value its role in producing intermediates for antidepressants and antiviral medications.
Safety and Storage
As a corrosive and flammable substance, handling requires proper ventilation (fume hood recommended) and explosion-proof equipment. Incompatible with strong oxidizers, acids, and acid chlorides—exothermic reactions may occur. Secondary containment is advised for bulk storage. For long-term preservation, amber glass bottles with PTFE-lined caps under nitrogen atmosphere prevent degradation. Shelf life typically exceeds 2 years when stored at 2-8°C. Spills should be neutralized with dilute acetic acid before absorption with inert material.
B2B Procurement Guide
Technical specifications should emphasize enantiomeric excess (ee ≥98%), water content (<0.5%), and residual solvent levels (typically methanol or hexanes). Reputable suppliers provide batch-specific chiral HPLC chromatograms and NMR spectra for verification. For pharmaceutical applications, ensure the supplier can deliver DMF (Drug Master File) or CEP (Certificate of Suitability) documentation. Container options range from 1kg glass bottles to 200kg stainless steel drums. Just-in-time delivery minimizes storage risks, while multi-kilogram orders often attract 10-15% price discounts.
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