319-39-1

Usage

Uses

Used in Agricultural Industry:
2',4'-Dichlorobenzanilide is used as a pesticide and insecticide for controlling nematodes, insects, and fungal diseases in various crops. It is effective in suppressing these pests by inhibiting the activity of acetylcholinesterase, an enzyme crucial for the proper functioning of the nervous system in pests, leading to their death.
However, it is important to use 2',4'-Dichlorobenzanilide with caution, as it can be harmful to humans and the environment if not handled properly. Proper safety measures and guidelines should be followed to minimize potential risks associated with its use.

InChI:InChI=1/C13H9Cl2NO/c14-9-5-7-10(8-6-9)16-13(17)11-3-1-2-4-12(11)15/h1-8H,(H,16,17)

Upstream product

• 118-91-2 ortho-chlorobenzoic acid 
• 637-87-6 1-Chloro-4-iodobenzene 
• 609-66-5 2-chlorobenzamide 
• 609-65-4 o-chlorobenzoyl chloride 
• 106-47-8 4-chloro-aniline 
• 2617-79-0 N-(4-chlorophenyl)formamide 
• 6833-13-2 2-chlorobenzanilide 

Downstream Products

• 27353-44-2 2-chlorophenanthridin-6(5H)-one 
• 54960-76-8 2-chloro-5-methylphenanthridin-6(5H)-one 
• 1372788-46-9 C₁₄H₁₁Cl₂NO 
• 1384754-97-5 [(C₆H₄C(O)NC₆H₄-4-Cl)Co(III)(Cl-ortho-C₆H₄C(O)NC₆H₄-4-Cl)(trimethylphosphine)2] 
• 33238-22-1 3-benzylidene-2-(4-chlorophenyl)isoindol-1-one 

Relevant academic research and scientific papers

Potassium Carbonate Promoted C-N Coupling Reaction between Benzamides and Aryl Iodides

A practical and efficient method for N-arylation of benz-amides promoted by potassium carbonate in the presence of DMEDA was developed. The reaction was carried out without addition of any transition-metal catalyst to afford a variety of N-arylated products in moderate to good yields (up to 97%).

Continuous flow photochemistry as an enabling synthetic technology: Synthesis of substituted-6(5: H)-phenanthridinones for use as poly(ADP-ribose) polymerase inhibitors

Methods utilizing continuous flow photochemistry, an enabling synthetic technology, have been developed for the generation of phenanthridinones via an intramolecular photochemical cyclization of 2-chlorobenzamides for the purposes of generating poly(ADP-ribose) polymerase inhibitors. Herein we report 16 examples of a single-step flow photocyclization which produces substituted phenanthridinones in yields up to 99%, while a two-step method leads directly to phenanthridinones from 2-chlorobenzoyl chlorides and anilines via a novel continuous flow amidation/photocyclization protocol. Overall, the flow photocyclization reactions typically progress in good to excellent yields, and in a superior fashion to analogous batch methods, greatly enabling the drug discovery process.

Direct arylation under catalysis of an oxime-derived palladacycle: Search for a phosphane-free method

A phosphane-free method for the direct arylation of benzothiazole by employing oxime-derived palladacycle 1 as a catalyst was developed. The new catalyst system can be used for 2-arylations by using aryl bromides and iodides. In addition, this method is especially suitable for the intramolecular direct coupling of bromo-and iodoamides, as well aschloroamides, to achieve a rapid synthesis of benzo[c]phenanthridine alkaloids. Direct arylation reactions under catalysis of an oxime-derived palladacycle were investigated. This phosphane-free method is applicable for the 2-arylation of benzothiazole and is especially suitable for the intramolecular direct coupling of bromo-and iodoamides, as well as chloroamides, to achieve rapid synthesis of benzo[c]phenanthridine alkaloids. Copyright

Substituted 2-phenyl-4-quinolone-3-carboxylic acid compounds and their use as antitumor agents

Substituted 2-phenyl-4-quinolone-3-carboxylic acid derivatives and their salts were synthesized. The results of preliminary screening revealed that these compounds are potent in killing solid tumor cancers.

Photocyclization of Aryl Halides. Part 3. Phenanthridone Photosynthesis from 2-Halogenobenzanilides

2-Chlorobenzanilides cyclize to phenanthridones in deaereted cyclohexane solution on 254 nm irradiation, whereas 2-bromo- and 2-iodo-benzanilides undergo dehalogenative reduction.These observations are understandable in terms of the assisted homolysis model as applied to configurationally flexible molecules.Cyclization in hydrocarbon media is retarted by triplet quenchers and fails in polar solvents.The cyclization can also be singlet and triplet sensitized. 4'-Substituents influence the cyclization quantum yield by altering the ?-donor ability of the aniline ring and the rotational barrier about the amide bond.

Reaction Pathways for Arylcarbamoyl Radicals and the Cyclization of o-Substituted Phenylcarbamoyl Radicals

N-Arylcarbamoyl radicals generated from N-arylformamides with di-t-butyl peroxide (ButOOBut) in chlorobenzene at 110 deg C give rise to a series of reactions depending on the nature and the position of the substituent in the aromatic ring.When the aryl group is phenyl or p-chlorophenyl the following reactions on carbamoyl radicals occur: (i) loss of hydrogen with formation of aryl isocyanates, whereas the loss of carbon monoxide leads to arylamines via arylaminyl radicals; (ii) dimerization to NN'-diaryloxamides; (iii) aromatic substitution on chlorobenzene leading to N-arylbenzamides (ipso-substitution) and N-arylchlorobenzamides.The isocyanates trapped by t-butyl alcohol and arylamines give t-butyl N-arylcarbamates and NN'-diarylureas.With o-substituted N-phenylformamides intramolecular cyclization is observed as well; in fact, the N-(o-cyanophenyl)formamide affords isatin via addition of the carbamoyl radical to the cyano-group while the N-formamide gives 2-benzothiazolone and phenyl radicals through an SHi reaction on the sulphur atom; finally 2-formamidobiphenyls furnish phenanthridones in very high yields.