1608149-98-9

Basic information

• Product Name: C₁₈H₂₂N₄O₂
• Synonyms: C₁₈H₂₂N₄O₂
• CAS NO: 1608149-98-9
• Molecular Weight: 326.398
• Mol File: 1608149-98-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: C₁₈H₂₂N₄O₂(CAS DataBase Reference)
• NIST Chemistry Reference: C₁₈H₂₂N₄O₂(1608149-98-9)
• EPA Substance Registry System: C₁₈H₂₂N₄O₂(1608149-98-9)

Safety Data

• Hazardous Substances Data: 1608149-98-9(Hazardous Substances Data)

Upstream product

• 1246287-59-1 C₁₄H₁₄N₄O₂ 
• 109-73-9 N-butylamine 

Relevant articles and documents

Aminolysis of an N-diazeniumdiolated amidine as an approach to diazeniumdiolated ammonia

Recent theoretical studies have suggested that the parent diazeniumdiolate ion, H2N-N(O)=NO- ( diazeniumdiolated ammonia ), might be stable enough to be isolated and that it could potentially serve as a uniquely advantageous prodrug form of bioactive nitroxyl (HNO). Here, we report on an attempt to isolate its O2-benzylated derivative by aminolysis of the C=N bond in PhC(NH2)=N-N(O)=NOBn. The reaction proved remarkably sluggish in comparison to aminolysis of unsubstituted benzamidine, and the desired product could not be isolated, apparently because of base sensitivity of the NH2 group. Consistent with this interpretation, O-benzylhydroxylamine and N2O were recovered from the reaction mixture in high yields, along with N,N′-dibutylbenzamidine. Theoretical calculations rationalize the observed slow aminolysis by demonstrating that the diazeniumdiolate group greatly suppresses the electrophilicity of the adjacent C=N carbon center, rendering attack at that position endothermic. The data provide significant insights into the challenges inherent to the pursuit of diazeniumdiolated ammonia.