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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
4-Meth-oxy-2-nitro-4'-(trifluoro-meth-yl)biphen-yl
Yan-Jun Hou1, Xin-Min Li, Wen-Yi Chu
1College of Chemistry and Materials Science, Heilongjiang University, Harbin 150080, People's Republic of China.
Acta Crystallographica. Section E, Structure Reports Online
|January 6, 2012
Summary
A novel trifluoromethyl-substituted nitrobenzene derivative was synthesized using palladium-catalyzed Suzuki-Miyaura coupling. Structural analysis revealed specific dihedral angles and trifluoromethyl group disorder in the crystal structure.
Area of Science:
- Organic Chemistry
- Crystallography
- Supramolecular Chemistry
Background:
- Suzuki-Miyaura coupling is a versatile method for carbon-carbon bond formation.
- Understanding molecular geometry and substituent effects is crucial in drug design and materials science.
- Trifluoromethyl groups significantly influence molecular properties like lipophilicity and metabolic stability.
Purpose of the Study:
- To synthesize a novel trifluoromethyl-substituted nitrobenzene derivative.
- To elucidate the solid-state structure of the synthesized compound using X-ray crystallography.
- To investigate the impact of the trifluoromethyl group on molecular conformation.
Main Methods:
- Palladium-catalyzed Suzuki-Miyaura coupling reaction for synthesis.
- Single-crystal X-ray diffraction for structural determination.
- Analysis of bond lengths, bond angles, and dihedral angles.
Main Results:
- Successful synthesis of the target compound C(14)H(10)F(3)NO(3).
- X-ray crystallography revealed a dihedral angle of 66.85° between the nitro group and its benzene ring.
- A dihedral angle of 49.98° was observed between the two phenyl rings.
- The trifluoromethyl (CF3) group exhibited disorder over two crystallographic sites.
Conclusions:
- The Suzuki-Miyaura coupling provides an efficient route to trifluoromethyl-substituted nitroaromatics.
- The determined crystal structure provides insights into the conformational preferences of such molecules.
- The observed CF3 group disorder may influence crystal packing and material properties.
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