2626-60-0

Basic information

• Product Name: 1-AMINO-1-ETHYLCYCLOHEXANE
• Synonyms: 1-AMINO-1-ETHYLCYCLOHEXANE;1-Ethyl-cyclohexylamine
• CAS NO: 2626-60-0
• Molecular Formula: C₈H₁₇N
• Molecular Weight: 127.22728
• Mol File: 2626-60-0.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-AMINO-1-ETHYLCYCLOHEXANE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-AMINO-1-ETHYLCYCLOHEXANE(2626-60-0)
• EPA Substance Registry System: 1-AMINO-1-ETHYLCYCLOHEXANE(2626-60-0)

Safety Data

• Hazardous Substances Data: 2626-60-0(Hazardous Substances Data)

Usage

Chemical class

Amine

Subclass

Cyclohexylamines

Structure

Alkyl-substituted derivative of cyclohexylamine

Composition

Cyclohexane ring with an attached ethyl group and an amino group at the first carbon atom

Industrial applications

Building block in the synthesis of pharmaceuticals and other organic compounds

Additional uses

Chiral auxiliary in asymmetric synthesis and as a ligand in catalysis

Hazards

Toxic if ingested or inhaled

Hazards

Causes skin and eye irritation upon contact

Safety precautions

Handle with care

Upstream product

• 108-94-1 cyclohexanone 
• 30389-18-5 1-Ethynylcyclohexylamine 
• 99064-87-6 N-(1-ethyl-cyclohexyl)-formamide 
• 1453-24-3 1-ethylcyclohexene 
• 142-96-1 dibutyl ether 
• 7664-93-9 sulfuric acid 
• 1193-81-3 rac-1-cyclohexylethanol 
• 151-50-8 potassium cyanide 
• 1940-18-7 1-ethylcyclohexanol 
• 1124-97-6 1-ethyl-cyclohexanecarboxylic acid amide 

Downstream Products

• 764588-50-3 1-phenethylcyclohexan-1-amine 
• 22691-72-1 1-Nitroso-1-aethyl-cyclohexan 

Relevant articles and documents

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Palladium-Catalyzed C(sp3)?H Arylation of Primary Amines Using a Catalytic Alkyl Acetal to Form a Transient Directing Group

C?H Functionalization of amines is a prominent challenge due to the strong complexation of amines to transition metal catalysts, and therefore typically requires derivatization at nitrogen with a directing group. Transient directing groups (TDGs) permit C?H functionalization in a single operation, without needing these additional steps for directing group installation and removal. Here we report a palladium catalyzed γ-C?H arylation of amines using catalytic amounts of alkyl acetals as transient activators (e.g. commercially available (2,2-dimethoxyethoxy)benzene). This simple additive enables arylation of amines with a wide range of aryl iodides. Key structural features of the novel TDG are examined, demonstrating an important role for the masked carbonyl and ether functionalities. Detailed kinetic (RPKA) and mechanistic investigations determine the order in all reagents, and identify cyclopalladation as the turnover limiting step. Finally, the discovery of an unprecedented off-cycle free-amine directed ?-cyclopalladation of the arylation product is reported.

Carbon Dioxide-Mediated C(sp3)-H Arylation of Amine Substrates

Elaborating amines via C-H functionalization has been an important area of research over the past decade but has generally relied on an added directing group or sterically hindered amine approach. Since free-amine-directed C(sp3)-H activation is still primarily limited to cyclization reactions and to improve the sustainability and reaction scope of amine-based C-H activation, we present a strategy using CO2 in the form of dry ice that facilitates intermolecular C-H arylation. This methodology has been used to enable an operationally simple procedure whereby 1° and 2° aliphatic amines can be arylated selectively at their γ-C-H positions. In addition to potentially serving as a directing group, CO2 has also been demonstrated to curtail the oxidation of sensitive amine substrates.