(1S,2S)-2-phenoxycyclopropan-1-amine

Base Information

• Chemical Name: (1S,2S)-2-phenoxycyclopropan-1-amine
• CAS No.: 702-27-2
• Molecular Formula: C₉H₁₁NO
• Molecular Weight: 149.192
• Mol file: 702-27-2.mol

Synonyms:Cyclopropylamine,2-phenoxy-, trans- (8CI)

Chemical Property of (1S,2S)-2-phenoxycyclopropan-1-amine

Chemical Property:

• Vapor Pressure: 0.0416mmHg at 25°C
• Boiling Point: 238.8°C at 760 mmHg
• Flash Point: 103.2°C
• Density: 1.144g/cm³

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• General Description: (1S,2S)-2-phenoxycyclopropan-1-amine, also known as trans-2-phenoxycyclopropylamine, is a thermodynamically stable isomer synthesized from phenyl vinyl ether and ethyl diazoacetate, followed by hydrolysis and Curtius degradation. It exhibits potential as a monoamine oxidase (MAO) inhibitor, though no significant difference in activity was observed between its cis and trans forms. (1S,2S)-2-phenoxycyclopropan-1-amine was studied for its pharmacological properties, including acute toxicity and duration of action, but no consistent MAO inhibitory distinction was noted between the isomers.

Technology Process of (1S,2S)-2-phenoxycyclopropan-1-amine

There total 1 articles about (1S,2S)-2-phenoxycyclopropan-1-amine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

→ trans-2-Phenoxy-cyclopropylamin (702-27-2,876-38-0,1126-87-0,5050-98-6)

Guidance literature:

trans-2-Phenoxy-cyclopropancarbohydroxamsaeure, 1.) Thionylchlorid, Toluol, 2.) konz. wss. Salzsaeure, Toluol;

DOI:10.1021/jm00328a005

Refernces

Synthesis of cis- and trans-2-phenoxycyclopropylamines and related compounds.

10.1021/jm00328a005

The research focuses on the synthesis and study of 2-phenoxycyclopropylamines, which are of interest due to their potential as monoamine oxidase (MAO) inhibitors. The synthesis process begins with the reaction between phenyl vinyl ether and ethyl diazoacetate in the presence of copper to produce ethyl 2-phenoxycyclopropanecarboxylate. This ester is then hydrolyzed to yield the corresponding acid, which can exist in cis and trans forms. The researchers were able to separate and characterize these isomers, with the trans form being more thermodynamically stable and produced in greater yield. The esters were further converted into hydrazides, which underwent the Curtius degradation to yield amines. The amines were obtained as colorless liquids and their properties were studied. The research also involved testing the MAO inhibitory activity of these compounds in vivo and in vitro, with findings indicating no consistent difference in activity between the cis and trans forms. Additionally, the duration of action, acute toxicity, and other pharmacological properties of the trans-2-phenoxycyclopropylamine were investigated.

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