23496-29-9

Basic information

• Product Name: 2,2-dichloro-N-methyl-N-phenylacetamide
• CAS NO: 23496-29-9
• Molecular Formula: C₉H₉Cl₂NO
• Molecular Weight: 218.0799
• Mol File: 23496-29-9.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 274.2°C at 760 mmHg
• Flash Point: 119.6°C
• Density: 1.328g/cm³
• Vapor Pressure: 0.00549mmHg at 25°C
• Refractive Index: 1.583
• CAS DataBase Reference: 2,2-dichloro-N-methyl-N-phenylacetamide(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2-dichloro-N-methyl-N-phenylacetamide(23496-29-9)
• EPA Substance Registry System: 2,2-dichloro-N-methyl-N-phenylacetamide(23496-29-9)

Safety Data

• Hazardous Substances Data: 23496-29-9(Hazardous Substances Data)

Usage

Use

Broad-spectrum, non-systemic, low toxicity insecticide

Application

Control of insects in various agricultural and horticultural crops

Mechanism of action

Affects the nervous system of insects, causing paralysis and death

Veterinary use

Control of external parasites on livestock

Environmental concern

Highly toxic to aquatic organisms

Risk

Poses a risk to the environment if not used properly and responsibly

Upstream product

• 79-36-7 dichloroacethyl chloride 
• 100-61-8 N-methylaniline 
• 36558-96-0 N-methyl-N-phenyltrichloroacetamide 
• 79-34-5 1,1,2,2-tetrachloroethane 
• 79-43-6 dichloro-acetic acid 
• 56-23-5 tetrachloromethane 
• 579-10-2 N-acetyl-N-methylaniline 
• 708-88-3 N-methyl-N-(trichlorovinyl)aniline 

Downstream Products

• 2620-05-5 N-methyl-2-chloroacetanilide 
• 1134192-65-6 4-(4-bromophenyl)-3-hydroxy-1-methylquinolin-2(1H)-one 
• 704-27-8 N-Methyl-N-phenyl-1.2-dichlor-vinylamin 
• 2210-39-1 N-Methyl-anilinoaethylen-1.2-bis-(tributylphosphonium)-dichlorid 

Relevant articles and documents

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Synthesis and Mechanistic Insights of the Formation of 3-Hydroxyquinolin-2-ones including Viridicatin from 2-Chloro- N,3-diaryloxirane-2-carboxamides under Acid-Catalyzed Rearrangements

N-Benzyl-2-chloro-N,3-diaryloxirane-2-carboxamides, easily obtained from aromatic aldehydes and anilides of dichloroacetic acid under Darzens condensation conditions, proved to be excellent starting compounds for the synthesis of 3-hydroxyindolin-2-ones, cyclohepto[b]pyrrole-2,3-diones, and 1-azaspiro[4.5]deca-3,6,9-triene-2-ones via the C(sp2)-C(sp2) bond formation in the first case and C(sp2)-C(sp3) bond formation in the second and third cases. Under optimized reaction conditions, 3-hydroxyindolin-2-ones are obtained in a one-pot process, which involves the treatment of N-benzyl-2-chloro-N,3-diaryloxirane-2-carboxamides with CF3CO2H or AcOH/H2SO4. In the case of intramolecular cyclization, the detailed reaction channels depend strongly on the substituents present in the anilide component and in the aromatic ring of the aldehyde component of N-benzyl-2-chloro-N,3-diaryloxirane-2-carboxamides, as well as the temperature and duration of the reaction. A combined experimental and DFT mechanistic study of the formation of 1-benzyl-3-hydroxy-4-arylquinolin-2(1H)-ones showed that there are three competing reaction channels: (a) ring-closure via the ipso site, (b) ring-closure via the 1,2-Cl shift, and (c) ring-closure via the ortho site. Such mechanistic insights enabled an effective one-pot gram-scale synthesis of viridicatin from benzaldehyde and 2,2-dichloro-N-(4-methoxybenzyl)-N-phenylacetamide.

Investigation of the Potential of Molybdenum(VI) Hydrazido(2-) Complexes as Sources of Nitrenium Ions: Cleavage of the N-N Bond and Incorporation of the β-Nitrogen Group into Solvent Molecules

Photolyis or thermolysis of bis(N,N-dimethyldithiocarbamato)bismolybdenum(VI) complexes in 1,1,2,2-tetrachloroethane results predominantly in transfer of the hydrazido group to the solvent with formation of dichloroacetohydrazides.A small amount of the corresponding dichloroacetamides are produced by N-N cleavage and N(R)Ph transfer.In contrast, the latter process dominates the reaction of dichlorobis(N,N-dimethyldithiocarbamato)mono-molybdenum(VI) complexes with silver nitrate in alcohols occuring concomitantly with ring methoxylation and nitration and N-nitrosation.Neither transfer of N(R)Ph appears to involve free nitrenium ions.