2-Aminopentanedinitrile

Base Information

• Chemical Name: 2-Aminopentanedinitrile
• CAS No.: 2478-50-4
• Molecular Formula: C5H7N3
• Molecular Weight: 109.131
• DSSTox Substance ID: DTXSID30542125
• Mol file: 2478-50-4.mol

Synonyms:2-aminopentanedinitrile;2478-50-4;SCHEMBL11035966;DTXSID30542125;AKOS006338576;EN300-747265

Chemical Property of 2-Aminopentanedinitrile

Chemical Property:

• XLogP3: -0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 109.063997236
• Heavy Atom Count: 8
• Complexity: 144

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C(CC(C#N)N)C#N

Refernces

Novel synthesis of 2-aminopentanedinitriles from 2-(bromomethyl)aziridines and their transformation into 2-imino-5-methoxypyrrolidines and 5-methoxypyrrolidin-2-ones

10.1016/j.tet.2007.03.116

The research focuses on the novel synthesis of 2-aminopentanedinitriles from 2-(bromomethyl)aziridines and their subsequent transformation into 2-imino-5-methoxypyrrolidines and 5-methoxypyrrolidin-2-ones. The study explores an unprecedented reaction mechanism involving base-induced ring opening of intermediate 2-(cyanomethyl)aziridines into allylamines, followed by migration of the double bond towards aldimines via enamine intermediates. The synthesized aminopentanedinitriles serve as precursors for the preparation of glutamic acid derivatives, which are significant in the central nervous system as excitatory neurotransmitters. The experiments utilized reactants such as 1-arylmethyl-2-(bromomethyl)aziridines, potassium cyanide in DMSO, and sodium methoxide in methanol. The analyses included column chromatography for purification, and various spectroscopic techniques such as NMR, IR, and MS for structural characterization and confirmation of the synthesized compounds.