5464-16-4

Basic information

• Product Name: 2-aminocyclopentanone
• CAS NO: 5464-16-4
• Molecular Formula: C₅H₉NO*ClH
• Molecular Weight: 99.1311
• Mol File: 5464-16-4.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 194.6°C at 760 mmHg
• Flash Point: 71.5°C
• Density: 1.068g/cm³
• Vapor Pressure: 0.437mmHg at 25°C
• Refractive Index: 1.488
• CAS DataBase Reference: 2-aminocyclopentanone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-aminocyclopentanone(5464-16-4)
• EPA Substance Registry System: 2-aminocyclopentanone(5464-16-4)

Safety Data

• Hazardous Substances Data: 5464-16-4(Hazardous Substances Data)

Usage

Also Known As

2-piperidinone

Chemical Classification

Cyclic amine, ketone

Common Uses

Building block in organic synthesis
Intermediate in the production of pharmaceuticals, agrochemicals, and fine chemicals
Precursor in the synthesis of heterocyclic compounds
Chiral auxiliary in asymmetric synthesis

Applications

Pharmaceutical industry
Research laboratories

Key Properties

Versatile intermediate
Modifiable for diverse compound synthesis

Upstream product

• 39871-47-1 α-azidocyclopentanone 

Relevant articles and documents

Synthesis of agelastatin A and derivatives premised on a hidden symmetry element leading to analogs displaying anticancer activity

Concise total syntheses of (±)-7-hydroxy debromo agelastatin A (AglA), (±)-AglA, and 11-nitro AglA are presented based on an identified pseudo-symmetry element. This synthetic strategy was developed based on a desire to improve solubility of this potent anticancer agent while also developing a synthetic strategy that would enable late-stage variation of the pyrrole moiety. A stability study of pyrrole-derived carbinolamines revealed critical substituent effects impacting the equilibrium between the cyclic carbinolamine and keto pyrrole forms. 7-Hydroxy AglA existed primarily in the ketopyrrole form however the des-bromo variant existed primarily in the cyclic carbinolamine form. Cytotoxicity assays revealed activity for a 13-nitro AglA derivative (～14–63 μM) for breast cancer cells (MDA-MB-231 and MCF7) and a glioblastoma cell line (U87) while for 7-hydroxy des-bromo AglA, measurable activity was only observed against the glioblastoma cell line.