27840-90-0

Usage

General Description

2-(cyclohexylamino)propan-1-ol is a chemical compound with the molecular formula C9H19NO. It is a tertiary amine with a cyclohexyl group and a hydroxyl group attached to a central carbon atom. The compound is commonly used as an intermediate in the synthesis of pharmaceuticals and agrochemicals, and also as a reagent in organic chemistry. It has been studied for its potential use in the treatment of neurodegenerative diseases and as a chiral auxiliary in stereoselective reactions. 2-(cyclohexylamino)propan-1-ol is a colorless liquid with a slightly amine-like odor and is soluble in water and organic solvents. It is important to handle 2-(cyclohexylamino)propan-1-ol with caution due to its potential hazards, including skin and eye irritation, and inhalation toxicity.

Upstream product

• 6168-72-5 2-Amino-1-propanol 
• 108-94-1 cyclohexanone 
• 1195-42-2 N-cyclohexylisopropylamine 
• 108-95-2 phenol 
• 108-91-8 cyclohexylamine 
• 116-09-6 hydroxy-2-propanone 

Relevant academic research and scientific papers

Iridium-Catalyzed, β-Selective C(sp3)-H Silylation of Aliphatic Amines to Form Silapyrrolidines and 1,2-Amino Alcohols

The functionalization of unactivated C(sp3)-H bonds of aliphatic amines catalyzed by transition-metal complexes is important because amine-based functionality is present in a majority of biologically active molecules and commercial pharmaceuticals. However, such reactions are underdeveloped and challenging to achieve in general because the basicity and reducing properties of alkylamines tends to interfere with potential reagents and catalysts. The functionalization of C-H bonds β to the nitrogen of aliphatic amines to form prevalent 1,2-amino functionalized structures is particularly challenging because the C-H bond β to nitrogen is stronger than the C-H bond α to nitrogen, and the nitrogen in the amine or its derivatives usually directs a catalyst to react at more distal γ- and δ-C-H bonds to form 5- or 6-membered metallacyclic intermediate. The enantioselective functionalization of a C-H bond at any position in amines also has been vexing and is currently limited to reactions of specific, sterically hindered, cyclic structures. We report iridium-catalyzed, β-selective silylations of unactivated C(sp3)-H bonds of aliphatic amines to form silapyrrolidines that are both silicon-containing analogs of common saturated nitrogen heterocycles and precursors to 1,2-amino alcohols by Tamao-Fleming oxidation. These silylations of amines are accomplished by introducing a simple methylene linker between the heteroatom and silicon that has not been used previously for the silylation of C-H bonds. The reactions occur with high enantioselectivity when catalyzed by complexes of new chiral, pyridyl imidazoline ligands, and the rates of reactions with catalysts of these highly basic ligands are particularly fast, occuring in some cases at or even below room temperature.

Domino Hydrogenation-Reductive Amination of Phenols, a Simple Process To Access Substituted Cyclohexylamines

Phenols can be efficiently reduced by sodium formate and Pd/C as the catalyst in water and in the presence of amines to give the corresponding cyclohexylamines. This reaction works at rt for 12 h or at 60 °C under microwave dielectric heating for 20 min. With the exception of aniline, primary, secondary amines, amino alcohols, and even amino acids can be used as nucleophiles. The reductive process is based on a sustainable hydrogen source and a catalyst that can be efficiently recovered and reused. The protocol was developed into a continuous-flow production of cyclohexylamines in gram scale achieving very efficient preliminary results (TON 32.7 and TOF 5.45 h-1).