5913-13-3

Basic information

• Product Name: (R)-(-)-1-Cyclohexylethylamine
• Synonyms: (R)-(-)-1-Cyclohexylethylamine;R(-)-ALPHA-METHYLCYCLOHEXANEMETHYLAMINE;(R)-(-)-1-CYCLOHEXYLETHYLAMINE;(R)-1-CYCLOHEXYLETHYLAMINE;Cyclohexanemethanamine, alpha-methyl-, (R)-;(R)-alpha-cyclohexanemethylamine;(R)-(-)-1-CYCLOHEXYLETHYLAMINE 98%;(r)-(-)-à-methylcyclohexanemethylamine
• CAS NO: 5913-13-3
• Molecular Formula: C₈H₁₇N
• Molecular Weight: 127.23
• EINECS: 227-634-2
• Product Categories: Amines (Chiral);Chiral Building Blocks;Synthetic Organic Chemistry
• Mol File: 5913-13-3.mol
• Article Data: 34

Chemical Properties

• Melting Point: -15°C (estimate)
• Boiling Point: 177-178 °C(lit.)
• Flash Point: 126 °F
• Appearance: /
• Density: 0.866 g/mL at 20 °C(lit.)
• Vapor Pressure: 1.2mmHg at 25°C
• Refractive Index: n20/D 1.463
• PKA: 10.89±0.29(Predicted)
• Water Solubility: Miscible with acetone, chloroform,dimethyl sulfoxide, ethanol, methanol, ether, petroleum ether and dichloromethane. Insoluble i
• Sensitive: Air Sensitive
• BRN: 2935070
• CAS DataBase Reference: (R)-(-)-1-Cyclohexylethylamine(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(-)-1-Cyclohexylethylamine(5913-13-3)
• EPA Substance Registry System: (R)-(-)-1-Cyclohexylethylamine(5913-13-3)

Safety Data

• Hazard Codes: C
• Statements: 10-21/22-34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 2734 8/PG 2
• WGK Germany: 3
• F: 3-10-23
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 5913-13-3(Hazardous Substances Data)

Usage

Description

(R)-(-)-1-Cyclohexylethylamine is an organic compound that features a cyclohexane ring attached to an ethylamine group. It is a chiral molecule, with the "R" configuration indicating the specific arrangement of atoms in its structure. (R)-(-)-1-Cyclohexylethylamine is known for its unique properties and reactivity, making it a valuable building block in the synthesis of various complex organic molecules.

Uses

Used in Pharmaceutical and Chemical Synthesis:
(R)-(-)-1-Cyclohexylethylamine is used as a key intermediate in the preparation of benzylidene(1-cyclohexylethyl)amine by reacting with benzaldehyde. This reaction is crucial for the synthesis of various pharmaceuticals and specialty chemicals that require chiral centers for their biological activity.
Used in Chiral Stationary Phases for Chromatography:
(R)-(-)-1-Cyclohexylethylamine is used to prepare chiral polymethacrylamides, which serve as stationary phases for the liquid-chromatographic resolution of racemic amides. These chiral stationary phases are essential for separating enantiomers, which is critical in the development and manufacturing of chiral drugs.
Used in High Performance Liquid Chromatography (HPLC):
(R)-(-)-1-Cyclohexylethylamine is also used in the preparation of polyamides bound to silica gel for high-performance liquid chromatography. These materials offer pressure stability and are used for the separation and analysis of various compounds in the pharmaceutical, chemical, and environmental industries.
Used in Chiral Calix[4]arene Schiff Base Derivatives:
Furthermore, (R)-(-)-1-Cyclohexylethylamine may be used in the preparation of chiral calix[4]arene Schiff base derivatives. These derivatives possess potential enantioselective recognition ability towards amines, which can be utilized in various applications such as chiral catalysts, sensors, and enantioselective separation techniques.

Purification Methods

Purify it by conversion to the bitartrate salt (m 172o), then decomposing with strong alkali and extracting into Et2O, drying (KOH), filtering, evaporating and distilling. The hydrochloride salt has m 242o (from EtOH/Et2O), [] D -5.0o (c 10 H2O, from (+) amine). The oxalate salt has m 132o (from H2O). The (±)-base has b 176-178o/760mm, and HCl has m 237-238o. [Reihlen et al. Justus Liebigs Ann Chem 532 247 1938, Leithe Chem Ber 65 660 1932, Beilstein 12 III 95.]

InChI:InChI=1/C8H17N/c1-7(9)8-5-3-2-4-6-8/h7-8H,2-6,9H2,1H3

Upstream product

• 618-36-0 rac-methylbenzylamine 
• 540-69-2 ammonium formate 
• 823-76-7 Cyclohexyl methyl ketone 
• 36065-27-7 N-α-phenylethylacetamide 
• 64-17-5 ethanol 
• 6948-01-2 N-formyl-α-methylbenzylamine 
• 16712-16-6 ammonium formate 
• 17430-98-7 [(1S)-1-cyclohexylethyl]amine 
• 1193-81-3 rac-1-cyclohexylethanol 
• 4352-49-2 1-cyclohexylethylamine 
• 3886-69-9 (R)-1-phenyl-ethyl-amine 
• 52316-19-5 cyclohexyl methyl ketone oxime 
• 142068-31-3 N'-(1-cyclohexylethylidene)benzohydrazide 
• 379686-28-9 (R)-1-cyclohexylethyl azide 

Downstream Products

• 854444-53-4 (1-cyclohexyl-ethyl)-dimethyl-amine 
• 138785-77-0 N-(1-cyclohexylethyl)formamide 
• 175653-27-7 (R)-N-(1-cyclohexylethyl)benzamide 
• 67404-89-1 N-(1-cyclohexylethyl)benzamide 
• 33290-14-1 ethyl (R)-(α-cyclohexylethyl)carbamate 
• 120205-93-8 N-((S)-1-Cyclohexyl-ethyl)-butyramide 
• 120205-93-8 N-((R)-1-Cyclohexyl-ethyl)-butyramide 
• 133175-26-5 (R)-N-((R)-1-Cyclohexyl-ethyl)-2-fluoro-2-phenyl-acetamide 
• 133175-42-5 (R)-N-((S)-1-Cyclohexyl-ethyl)-2-fluoro-2-phenyl-acetamide 
• 77507-17-6 N-(1-Cyclohexylethyl)-α-<1-(9-anthryl)-2,2,2-trifluoroethoxy>acetamide 
• 41122-67-2 (R) N-benzylidene-1-cyclohexylethylamine 
• 158072-26-5 N,N′-(R)-(-)-1-cyclohexylethylthiourea 

Relevant articles and documents

Sequential Chiral Induction and Regulator-Assisted Chiral Memory of Pillar[5]arenes

Chirality transfer is widely observed in life processes, and many artificial chiral transfer systems have been developed. In these systems, chiral information is transferred from chiral inducers to chiral acceptors by a direct chiral induction process and a direct chiral memorization process. We have developed ternary nondirect chiral transfer systems based on pillar[5]arenes, in which a third factor was introduced as a regulator. The planar chirality of an acceptor was induced and memorized by a chiral inducer with precise control by a regulator. In the chiral induction period, the feed sequence of the chiral inducer and regulator affected the chiral induction behavior of the chiral acceptor. The chiral memory ability of the acceptor was substantially improved by the combined action of the chiral inducer and regulator.

Direct Synthesis of α-Amino Nitriles from Sulfonamides via Base-Mediated C-H Cyanation

Herein, we disclose a transition-metal-free reaction system that enables α-cyanation of sulfonamides through C-H bond cleavage for the preparation of α-amino nitriles, including difficult-to-access all-alkyl α-tertiary scaffolds. More than 50 substrate examples prove a wide functional group tolerance. Additionally, its synthetic practicality is highlighted by gram-scalability and the late-stage modification of natural compounds. Mechanistic experiments suggest that this process involves in situ formation of an imine intermediate via base-promoted elimination of HF.

Ruthenium Catalyzed Direct Asymmetric Reductive Amination of Simple Aliphatic Ketones Using Ammonium Iodide and Hydrogen

The direct conversion of ketones into chiral primary amines is a key transformation in chemistry. Here, we present a ruthenium catalyzed asymmetric reductive amination (ARA) of purely aliphatic ketones with good yields and moderate enantioselectivity: up to 99 percent yield and 74 percent ee. The strategy involves [Ru(PPh3)3H(CO)Cl] in combination with the ligand (S,S)-f-binaphane as the catalyst, NH4I as the amine source and H2 as the reductant. This is a straightforward and user-friendly process to access industrially relevant chiral aliphatic primary amines. Although the enantioselectivity with this approach is only moderate, to the extent of our knowledge, the maximum ee of 74 percent achieved with this system is the highest reported till now apart from enzyme catalysis for the direct transformation of ketones into chiral aliphatic primary amines.