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Updated: Jun 1, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
1-(4-Bromo-3-chloro-phen-yl)-3-meth-oxy-3-methyl-urea (chlorbromuron)
Harrison M Black1, Russell G Baughman
1Department of Chemistry, Truman State University, Kirksville, MO 63501-4221, USA.
Abstract:
In the title urea-based herbicide, C(9)H(10)BrClN(2)O(2), there exist multiple inter- and intra-molecular inter-actions. Most notably, the intra-molecular hydrogen bond between the urea carbonyl O atom and an aromatic H atom affects the planarity and torsion angles of the mol-ecule by restricting rotations about the Ar-secondary amine N and the secondary amine N and the carbonyl C. The two N atoms in the urea fragment are in different environments. One is planar; the other, pseudo-C(3v). It is likely that the different nitro-gen-atom geometries and the restricted rotations within the mol-ecule impact the bioactivity of chlorbromuron.
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