114-38-5

Usage

Uses

Used in Agricultural and Horticultural Applications:
O-Chlorophenylurea is used as a herbicide for controlling the growth of weeds, thereby promoting the growth of desired crops. It achieves this by disrupting the photosynthesis and cell division processes in plants, effectively inhibiting their growth.
Used in Pharmaceutical Applications:
Due to its unique chemical structure, O-Chlorophenylurea has potential uses in the pharmaceutical industry, where it may be utilized in the synthesis of other organic compounds or as a precursor for developing new drugs.
Used in Chemical Synthesis:
O-Chlorophenylurea also finds application in the synthesis of various organic compounds, contributing to the development of new chemical entities for diverse industrial uses.

InChI:InChI=1/C7H7ClN2O/c8-5-3-1-2-4-6(5)10-7(9)11/h1-4H,(H3,9,10,11)

Upstream product

• 64-10-8 phenyl carbamate 
• 95-51-2 o-chloroaniline 
• 64-19-7 acetic acid 
• 5344-82-1 o-chlorophenylthiourea 
• 3320-83-0 o-chlorophenyl isocyanate 
• 103-71-9 phenyl isocyanate 
• 108-90-7 chlorobenzene 
• 57-13-6 urea 
• 45765-25-1 (2-chlorophenyl)cyanamide 
• 56935-60-5 2-chloro-benzamide oxime 
• 873-32-5 2-Chlorobenzonitrile 
• 917-61-3 sodium isocyanate 

Downstream Products

• 75370-59-1 6-chloro-2,4-dinitrophenyl urea 
• 2272-28-8 N,N',N''-tris-(2-chloro-phenyl)-[1,3,5]triazine-2,4,6-triamine 
• 80636-53-9 (2-Chloro-phenyl)-(4,5-dimethyl-oxazol-2-yl)-amine 
• 210235-59-9 1-(2-Chloro-phenyl)-3-((E)-2-cyano-3-oxo-3-phenyl-propenyl)-urea 
• 35426-69-8 o-chlorobenzenecarbamic acid tert-butyl ester 
• 35580-76-8 N-(2-chlorophenyl)hydrazinecarboxamide 
• 1173547-39-1 1-(2-chlorophenyl)-3-(4-(3,4-dimethoxyphenethylamino)-6-(2-oxo-2H-chromen-4-yloxy)-1,3,5-triazin-2-yl)-urea 
• 1227464-80-3 2-{(coumarin-3-yl-1,3,4-oxadiazolyl)-5-thio}-4-(morpholino)-6-(2-chlorophenylureido)-s-triazine 
• 1333415-71-6 C₁₃H₁₁ClN₂O₃ 

Relevant academic research and scientific papers

Catalytic hydration of cyanamides with phosphinous acid-based ruthenium(ii) and osmium(ii) complexes: scope and mechanistic insights

The synthesis of a large variety of ureas R1R2NC(O)NH2 (R1 and R2 = alkyl, aryl or H; 26 examples) was successfully accomplished by hydration of the corresponding cyanamides R1R2NCN using the phosphinous acid-based complexes [MCl2(η6-p-cymene)(PMe2OH)] (M = Ru (1), Os (2)) as catalysts. The reactions proceeded cleanly under mild conditions (40-70 °C), in the absence of any additive, employing low metal loadings (1 molpercent) and water as the sole solvent. In almost all the cases, the osmium complex 2 featured a superior reactivity in comparison to that of its ruthenium counterpart 1. In addition, for both catalysts, the reaction rates observed for the hydration of the cyanamide substrates were remarkably faster than those involving classical aliphatic and aromatic nitriles. Computational studies allowed us to rationalize all these trends. Thus, the calculations indicated that the presence of a nitrogen atom directly linked to the CN bond depopulates electronically the nitrile carbon by inductive effect when coordinated to the metal center, thus favouring the intramolecular nucleophilic attack of the OH group of the phosphinous acid ligand to this carbon. On the other hand, the higher reactivity of Os vs. Ru seems to be related with the lower ring strain on the incipient metallacycle that starts to form in the transition state associated with this key step in the catalytic cycle. Indirect experimental evidence of the generation of the metallacyclic intermediates was obtained by studying the reactivity of [RuCl2(η6-p-cymene)(PMe2OH)] (1) towards dimethylcyanamide in methanol and ethanol. The reactions afforded compounds [RuCl(η6-p-cymene)(PMe2OR)(NCNMe2)][SbF6] (R = Me (5a), Et (5b)), resulting from the alcoholysis of the metallacycle, which could be characterized by single-crystal X-ray diffraction. This journal is

Efficient Direct Halogenation of Unsymmetrical N -Benzyl- and N -Phenylureas with Trihaloisocyanuric Acids

A simple and efficient methodology for the direct halogenation of N -phenylureas was developed using trihaloisocyanuric acids in acetonitrile at room temperature. This protocol proved to be effective for the construction of N -phenylureas with different patterns of substitution. Additionally, less reactive N -benzylureas were halogenated in the presence of a mixture of trifluoroacetic acid and acetonitrile at room temperature.

Teaching Old Compounds New Tricks: DDQ-Photocatalyzed C?H Amination of Arenes with Carbamates, Urea, and N-Heterocycles

The C?H amination of benzene derivatives was achieved using DDQ as photocatalyst and BocNH2 as the amine source under aerobic conditions and visible light irradiation. Electron-deficient and electron-rich benzenes react as substrates with moderate to good product yields. The amine scope of the reaction comprises Boc-amine, carbamates, pyrazoles, sulfonimides and urea. Preliminary mechanistic investigations indicate arene oxidation by the triplet of DDQ to radical cations with different electrophilicity and a charge transfer complex between the amine and DDQ as intermediate of the reaction.

Novel Imidazoles for the Treatment and Prophylaxis of Respiratory Syncytial Virus Infection

The invention provides novel compounds having the general formula: wherein R1, R2, R3 and Q are as described herein, compositions including the compounds and methods of using the compounds.

Design and biological evaluation of novel 4-(2-fluorophenoxy)quinoline derivatives bearing an imidazolone moiety as c-Met kinase inhibitors

A series of 4-(2-fluorophenoxy)quinoline derivatives containing an imidazolone moiety were designed, synthesized and evaluated for their in vitro biological activities against c-Met kinase and four cancer cell lines (A549, H460, HT-29 and MKN-45). Most compounds showed moderate to excellent activities in enzyme and cellular assays. The most promising analog, 58 (c-Met IC50 = 1.42 nM), displayed 2.1-, 8.6-fold increase against H460, and MKN-45 cell lines, respectively, compared with foretinib. An analysis of structure-activity relationships revealed that an ortho substituted phenyl ring as well as an N-unsubstituted imidazolone linker is favorable for antitumor activity.

IMIDAZOLES FOR THE TREATMENT AND PROPHYLAXIS OF RESPIRATORY SYNCYTIAL VIRUS INFECTION

The invention provides novel compounds having the general formula: (I) wherein R1, R2, R3 and Q are as described herein, compositions including the compounds and methods of using the compounds.

One-Pot Synthesis of N-Monosubstituted Ureas from Nitriles via Tiemann Rearrangement

Amidoximes, obtained from the reaction of nitriles with hydroxylamine, underwent Tiemann rearrangement in the presence of benzenesulfonyl chlorides (TsCl or o-NsCl) to form the N-substituted cyanamides. Subsequently, acidic hydrolysis of the cyanamides afforded the corresponding N-monosubstituted ureas. The synthesis of N-monosubstituted ureas from nitriles was accomplished by three steps in one pot, which provides a direct access to versatile N-monosubstituted urea derivatives from a wide variety of nitriles.

Synthesis and anticonvulsant evaluation of 2-(substituted benzylidene/ethylidene)-N-(substituted phenyl)hydrazinecarboxamide analogues

In the present investigation, we described herein the molecular properties prediction by Molinspiration (2008) and synthesized a series of 17 2-(substituted benzylidene/ethylidene)-N-(substituted phenyl) hydrazinecarboxamide analogues. All the title compounds (4a-q) followed the Lipinski "Rule of Five." The synthesized compounds were characterised by elemental analyses and spectral data followed by anticonvulsant activity according to the Antiepileptic Drug Development Programme Protocol. 2-(4-Hydroxybenzylidene)-N-(2-chlorophenyl)hydrazinecarboxamide (4j) was found to be the most active compound of the series showing protection at 4.0 h at a dose of 100 mg/kg against maximal electroshock seizure test and 50 % (2/4, 0.25, 1-2 h) and 100 % (4/4, 0.5 h) protection in 6 Hz psychomotor seizure test without showing any neurotoxicity. N-(2-chlorophenyl)hydrazine carboxamide (3b) showed 100 % (4/4, 0.25-2 h) and 66.6 % (2/3, 4 h) protection in 6 Hz psychomotor seizure test.

Synthesis and crystal structure of N-(3-benzylamino-2-cyano-3- methylthioacrylyl)-N′-(substituted phenyl)ureas

Phenylurea groups were introduced into the frame of traditional cyanoacrylate and a series of N-(3-benzylamino-2-cyano-3-methylthioacrylyl)- N′-(substituted phenyl)ureas were synthesized. All compounds are new and their structures were confirmed by 1H NMR, 13C NMR and mass spectral analyses.