Glycinamide

Glycinamide is an organic compound with the molecular formula H₂NCH₂C(O)NH₂. It is the amide derivative of the amino acid glycine. It is a water-soluble, white solid. Amino acid amides, such as glycinamide are prepared by treating the amino acid ester with ammonia.^[1]

Glycinamide

Names
Preferred IUPAC name 2-Aminoacetamide
Identifiers
CAS Number	598-41-4 Y 1668-10-6 (HCl)
3D model (JSmol)	Interactive image
ChemSpider	62242
ECHA InfoCard	100.009.031
PubChem CID	69020
UNII	4JDT453NWO Y
CompTox Dashboard (EPA)	DTXSID1060508
SMILES C(C(=O)N)N
Properties
Chemical formula	C2H6N2O
Molar mass	74.083 g·mol−1
Appearance	white solid
Melting point	65–67 °C (149–153 °F; 338–340 K)
Boiling point	decomposes
Solubility in water	good
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

It is a ligand for transition metals, related to amino acid complexes. As a neutral ligand, it binds through the amine. In some complexes, it binds through the amine and the carbonyl oxygen, forming a five-membered chelate ring.^[2]

The hydrochloride salt of glycinamide, glycinamide hydrochloride, is one of Good's buffers with a pH in the physiological range. Glycinamide hydrochloride has a pKa near the physiological pH (8.20 at 20°C), making it useful in cell culture work. Its ΔpKa/°C is -0.029 and it has a solubility in water at 0 °C of 6.4 M.

Glycinamide is a reagent used in the synthesis of glycineamide ribonucleotide (an intermediate in de novo purine biosynthesis).^[3]