Aminomalononitrile

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Aminomalononitrile
Aminomalononitrile.svg
Names
Other names
2-aminomalononitrile, AMN
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/C3H3N3/c4-1-3(6)2-5/h3H,6H2
    Key: GXDKXRIMUVUELI-UHFFFAOYSA-N
  • C(#N)C(C#N)N
Properties
C3H3N3
Molar mass 81.078 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Aminomalononitrile (AMN) is the organic compound with the formula H2NCH(CN)2. The compound can be viewed as an amine-substituted malononitrile. It is of some interest to the study of the chemical origin of life because it represents a trimer of HCN, speculated to be a progenitor of nucleic acids. [1] Aminomalononitrile has been prepared by reduction of the oxime: HONC=(CN)2 with aluminium amalgam. The compound is used in situ but can be isolated as its tosylate salt [H3NCH(CN)2]OTs where -OTs is CH3C6H4SO−3. [2]

AMN Synthese (cropped).svg

AMN reacts with cyanide to give diaminomaleonitrile, a tetramer of HCN:

DAMN aus AMN (cropped).svg

This easy conversion has been the source of some confusion.

References

  1. ↑ Ruiz-Bermejo, Marta; Zorzano, María-Paz; Osuna-Esteban, Susana (2013). "Simple Organics and Biomonomers Identified in HCN Polymers: An Overview". Life. 3 (3): 421–448. Bibcode:2013Life....3..421R. doi: 10.3390/life3030421 . PMC   4187177 . PMID   25369814.
  2. ↑ Ferris, J. P.; Sanchez, R. A.; Mancuso, R. W. (1968). "Aminomalononitrile p-Toluenesulfonate". Organic Syntheses. 48: 1. doi:10.15227/orgsyn.048.0001.
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