Chemistry:Aminomalononitrile
From HandWiki
Aminomalononitrile (AMN) is the organic compound with the formula H
2NCH(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 [H
3NCH(CN)
2]OTs where -OTs is CH
3C
6H
4SO−
3.[2]
- Image:AMN Synthese (cropped).svg
AMN reacts with cyanide to give diaminomaleonitrile, a tetramer of HCN:
- Image: DAMN aus AMN (cropped).svg
This easy conversion has been the source of some confusion.
References
- ↑ 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. doi:10.3390/life3030421. PMID 25369814. Bibcode: 2013Life....3..421R.
- ↑ 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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