15216-10-1

Basic information

• Product Name: nitrosoazetidine
• Synonyms: nitrosoazetidine;N-NITROSOAZETIDINE;1-NITROSOAZETIDINE
• CAS NO: 15216-10-1
• Molecular Formula: C₃H₆N₂O
• Molecular Weight: 86.11
• Mol File: 15216-10-1.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 158.75°C (rough estimate)
• Flash Point: 75.8°C
• Appearance: /
• Density: 1.1530 (rough estimate)
• Vapor Pressure: 0.432mmHg at 25°C
• Refractive Index: 1.5110 (estimate)
• PKA: -3.14±0.20(Predicted)
• CAS DataBase Reference: nitrosoazetidine(CAS DataBase Reference)
• NIST Chemistry Reference: nitrosoazetidine(15216-10-1)
• EPA Substance Registry System: nitrosoazetidine(15216-10-1)

Safety Data

• Hazardous Substances Data: 15216-10-1(Hazardous Substances Data)

Usage

Safety Profile

Moderately toxic by ingestion.Questionable carcinogen with experimental tumorigenicdata. Mutation data reported. Many N-nitroso compoundsare carcinogens. When heated to decomposition it emitstoxic fumes of NOx.

InChI:InChI=1/C3H6N2O/c6-4-5-2-1-3-5/h1-3H2

Upstream product

• 503-29-7 azetidine 
• 543-67-9 n-propyl nitrite 
• 544-16-1 n-Butyl nitrite 

Relevant articles and documents

Structural features of aliphatic N-nitrosamines of 7-azabicyclo[2.2.1]heptanes that facilitate N-NO bond cleavage

N-Nitrosamines can be considered as potential nitric oxide (NO)/nitrosonium ion (NO+) donors. However, the relation of the structures of N-nitrosamines, in particular of aliphatic N-nitrosamines, to the characteristics of release of NO or NO+ remains unclear. Here we show that aliphatic N-nitrosoamines of 7-azabicyclo[2.2.1]heptanes can undergo heterolytic N-NO bond cleavage. On the basis of the observation of reduced rotational barriers of the N-NO bonds in solution and nitrogen-pyramidal structures of the N-nitroso group in the solid state, we postulate that N-NO bond cleavage of N-nitrosamines is enhanced by a reduction of the resonance in the N-NO group. Computational studies suggest that these structural features of the N-nitrosamines of 7-azabicyclo[2.2.1]heptane are derived from angle strain imposed on the CNC angles.

WEAKENING OF AMIDE CONJUGATION WITH A NITROGEN ATOM INCLUDED IN A FOUR-MEMBERED RING

The barriers to amide rotation about the N-N bond in 1-nitrosoazetidine, dimethylnitrosamine, 1-formylazetidine, 1,1'-carbonylbisazetidine, 1-dimethylcarbamoylazetidine, and dimethylformamide were measured by dynamic NMR spectroscopy. 1,1'-Carbonylbisazetidine and 1-dimethylcarbamoylazetidine, the structures of which were confirmed by data from the PMR and 13C NMR spectra, were obtained.