3-Hydroxypropionitrile CAS 109-78-4 Purity >98.0% (GC)

3-Hydroxypropionitrile (Ethylene Cyanohydrin) (CAS: 109-78-4) is used as pharmaceutical, organic synthesis intermediates.
3-Hydroxypropionitrile is an aliphatic nitrile to which a hydroxyl group is attached at the ?-carbon. The nitrogen atom contains a lone pair of electrons, which is largely responsible for the polarization of the C≡N triple bond. Because of the greater electronegativity of nitrogen compared to carbon, nucleophilic compounds can attack the electrophilic carbon atom (Schaefer 1970), although the nitrogen atom is an excellent donor site for complexing with Lewis acids (Sheppard 1970). The hydroxyl functional group on the other end of the molecule is also polar; like the nitrile nitrogen, its oxygen is basic and nucleophilic. Reactions of the -OH group can involve the breaking of either of two bonds: the C-OH bond, with removal of the -OH group; or the O-H bond, with removal of -H. Either kind of reaction can involve substitution, in which a group replaces the -H or -OH, or elimination, in which a double bond is formed (Morrison and Boyd 1973).
3-Hydroxypropionitrile has been used as polar solvent to investigate the orientation of the phospholipid at the surface of the polar solvents by neutral impact collision ion scattering spectroscopy and as a reagent for carboxyl protection in peptide synthesis. It has been used also in solid state composite electrolyte for dye-sensitized solar cells.