2-(4-Bromophenoxy)propanohydrazide

Abstract

The title compound, C9H11BrN2O2, is an important inter­mediate for the synthesis of heterocyclic compounds such as azoles, 2,5-disubstituted-1,3,4-oxadiazo­les and 5-substituted 2-mercapto-1,3,4-oxadiazo­les. The bromo­phen­oxy group subtends a dihedral angle of 82.81 (7)° with the plane passing through the propanohydrazide moiety. The crystal structure is stabilized by inter­molecular N—H⋯O hydrogen bonds that form columns extending along the b axis.

2-(4-Chlorophenoxy)acetohydrazide

“…For background to hydrazides, see: Cajocorius et al (1977); Liu et al (2006); Narayana et al (2005). For related structures, see: Akhtar et al (2009); Lokanath et al (1998); Mahendra et al (2004); Podyachev et al (2007). For graph-set symbols, see: Bernstein et al (1995).…”

“…This planar and (Z)-NCCO conformation was sometimes ascribed to the doubtful intramolecular N-H•••O hydrogen bond. When the steric hindrance is present, as for instance in the structure of 2-(4-bromophenoxy)propanohydrazide (Akhtar et al, 2009), the two planar fragments become almost perpendicular, dihedral angle between them is 84.9°.…”