43730-26-3

Basic information

• Product Name: N-Cyanomethanimine
• Synonyms: Methylenecyanamide;N-Cyanoformimine;N-Cyanomethanimine
• CAS NO: 43730-26-3
• Molecular Formula: C₂H₂N₂
• Molecular Weight: 0
• Mol File: 43730-26-3.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-Cyanomethanimine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Cyanomethanimine(43730-26-3)
• EPA Substance Registry System: N-Cyanomethanimine(43730-26-3)

Safety Data

• Hazardous Substances Data: 43730-26-3(Hazardous Substances Data)

Upstream product

• 290-87-9 1,3,5-Triazine 
• 5817-87-8 Trimethylenetetrazole 

Relevant articles and documents

HCN dimers: Iminoacetonitrile and N-cyanomethanimine

Iminoacetonitrile (1) has been prepared by two methods: (i) thermal decomposition of the tosylhydrazone salts 13 at 200 °C and (ii) Ar matrix photolysis of azidoacetonitrile (15). Ab initio calculations indicate that 1Z is of slightly lower energy than IE, and this is confirmed by the 1R spectra with use of the thermal methods. 1E/1Z undergo photochemical interconversion, giving a ca. 3:1 photostationary E:Z ratio. 1E and 1Z are fully characterized by their gas-phase, matrix, and thin-film IR spectra, which are in excellent agreement with ab initio calculations, by 1H and 13C NMR spectroscopy in solution, and by mass spectrometry. 1 polymerizes in solution above -40 °C; pyrolysis produces HCN, and matrix photolysis produces HNC and van der Waals complexes containing HNC. N-tert-Butyliminoacetonitrile thermally fragments to tert-butyl isocyanide and HCN. N-Cyanomethanimine (3) has also been prepared by two methods: (i) pyrolysis of trimethylenetetrazole (20) at 500-800 °C and (ii) pyrolysis of ditetrazolopyrazine 22 at 600-850 °C. Both methods are extremely clean. 3 is fully characterized by its IR spectrum in agreement with ab initio calculations and, in conjunction with other work, by its mass and millimeter-wave spectra. 3 is thermodynamically stable in the gas phase up to ca. 800 °C at low pressure and short contact times but polymerizes in the solid state above -100 °C.

Three-body photodissociation of 1,3,5-triazine

The three-body dissociation of 1,3,5-triazine (H3C3N3 → 3HCN) has been studied by molecular beam photofragment translational spectroscopy following excitation at 308, 295, 285, 275, 248, and 193 nm. The analysis of the measured translational energy distributions of the HCN photofragments has shown that the dissociation mechanism is not, as previously suggested, a symmetric (or synchronous) three-body process but rather is a two-step concerted process, where concerted refers to correlation between the asymptotic velocity vectors of the three ejected HCN fragments. Furthermore, there is evidence that the initially excited electronic state (1E″, 1A2) is deactivated by radiationless processes (internal conversion/intersystem crossing) to a lower electronic and finally dissociative state which is, according to symmetry correlation, the electronic ground state (electronic predissociation).