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Updated: Jun 1, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
(E)-4-Bromo-N-(2,3-dimeth-oxy-benzyl-idene)aniline
A novel Schiff base compound, C(15)H(14)BrNO(2), was synthesized. Its crystal structure reveals an E configuration and specific dihedral angles, with weak intermolecular interactions observed.
Area of Science:
- Organic Chemistry
- Crystallography
- Supramolecular Chemistry
Background:
- Schiff bases are versatile organic compounds with diverse applications.
- Understanding the structural and electronic properties of Schiff bases is crucial for designing new materials.
- The synthesis and characterization of novel Schiff base derivatives contribute to the field of organic synthesis.
Purpose of the Study:
- To synthesize a new Schiff base compound with the molecular formula C(15)H(14)BrNO(2).
- To elucidate the crystal structure and molecular geometry of the synthesized Schiff base.
- To investigate the intermolecular interactions present in the solid state.
Main Methods:
- Condensation reaction between 2,3-dimethoxy-benzaldehyde and 4-bromo-aniline.
- Single-crystal X-ray diffraction analysis to determine the crystal structure.
- Analysis of bond lengths, bond angles, dihedral angles, and intermolecular interactions (C-H⋯O, C-H⋯π).
Main Results:
- The Schiff base compound C(15)H(14)BrNO(2) was successfully synthesized.
- The crystal structure confirmed an E configuration around the C=N imine bond.
- A dihedral angle of 56.79(8)° was measured between the two aromatic rings.
- Weak C-H⋯O and C-H⋯π interactions were identified in the crystal lattice.
Conclusions:
- The synthesis yielded the target Schiff base with the expected molecular formula.
- The structural analysis provides detailed geometric information about the molecule in the solid state.
- The presence of weak interactions suggests potential for supramolecular assembly and crystal engineering.
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