Aminoacetaldehyde

Aminoacetaldehyde
Names
	Preferred IUPAC name Aminoacetaldehyde
	Other names H-Gly-al; glycynal
Identifiers
CAS Number	6542-88-7;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:17628;
ChEMBL	ChEMBL296723;
ChemSpider	356;
KEGG	C06735;
PubChem CID	363;
UNII	75G7022MOD;
CompTox Dashboard (EPA)	DTXSID50215728 ;
	InChI InChI=1S/C2H5NO/c3-1-2-4/h2H,1,3H2 Key: LYIIBVSRGJSHAV-UHFFFAOYSA-N;
	SMILES C(C=O)N;
Properties
Chemical formula	C2H5NO
Molar mass	59.068 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Aminoacetaldehyde is the organic compound with the formula OHCCH₂NH₂. Under the usual laboratory conditions, it is unstable, tending instead to undergo self-condensation.^[1] Aminoacetaldehyde diethylacetal is a stable surrogate.^[2]

In nature, aminoacetaldehyde is produced by oxygenation of taurine catalyzed by taurine dioxygenase, which produces the sulfite H₂NCH₂CH(OH)SO₃⁻.

References

^ Fisher, Lawrence E.; Muchowski, Joseph M. (1990). "Synthesis of α-Aminoaldehydes and α-Aminoketone. A Review". Organic Preparations and Procedures International. 22 (4): 399–484. doi:10.1080/00304949009356309.
^ Amato, Francesco; Marcaccini, Stefano (2005). "2,2-Diethoxy-1-Isocyanoethane". Organic Syntheses. 82: 18. doi:10.15227/orgsyn.082.0018.