14985-83-2

Usage

Physical form

White crystalline solid

Uses

Broad-spectrum antimicrobial agent in industrial and agricultural applications, used in paints, adhesives, water treatment chemicals, and synthesis of other organic compounds

Mechanism of action

Inhibits bacterial growth

Safety precautions

Classified as harmful if swallowed, inhaled, or in contact with skin and eyes, recommended to use appropriate protective equipment and follow safety guidelines when handling

InChI:InChI=1/C9H9Cl2NO/c1-6-4-2-3-5-7(6)12-9(13)8(10)11/h2-5,8H,1H3,(H,12,13)

Upstream product

• 79-43-6 dichloro-acetic acid 
• 95-53-4 o-toluidine 
• 60-29-7 diethyl ether 
• 141-82-2 malonic acid 
• 535-15-9 ethyl 1,1-dichloroacetate 
• 79-36-7 dichloroacethyl chloride 
• 93-68-5 3-oxo-N-o-tolylbutanamide 

Relevant academic research and scientific papers

Synthesis, structural, vibrational and quantum chemical investigations of N-(2-methylphenyl)-2,2-dichloroacetamide and N-(4-methylphenyl)-2,2-dichloroacetamide

N-(2-Methylphenyl)-2,2-dichloroacetamide (2MPA) and N-(4-methylphenyl)-2,2-dichloroacetamide (4MPA) of the configuration XyC6H5-y-NHCO-CHCl2 (where, X = CH3 and y = 1) were synthesised and an extensiv

Dichloromeldrum's acid (DiCMA): A practical and green amine dichloroacetylation reagent

Dichloromeldrum's acid is introduced as a bench-stable, nonvolatile reagent for the dichloroacetylation of anilines and alkyl amines to produce α,α-dichloroacetamides, which are important motifs for medicinal chemistry. Products are formed in good to excellent yields with reagent grade solvents, and, as the only byproducts are acetone and CO2, no column chromatography is required. Thus, this reagent is practical, efficient, and green for the dichloroacetylation of primary amines.

Dichloroacetophenones targeting at pyruvate dehydrogenase kinase 1 with improved selectivity and antiproliferative activity: Synthesis and structure-activity relationships

Dichloroacetophenone is a pyruvate dehydrogenase kinase 1 (PDK1) inhibitor with suboptimal kinase selectivity. Herein, we report the synthesis and biological evaluation of a series of novel dichloroacetophenones. Structure-activity relationship analyses (SARs) enabled us to identify three potent compounds, namely 54, 55, and 64, which inhibited PDK1 function, activated pyruvate dehydrogenase complex, and reduced the proliferation of NCI-H1975 cells. Mitochondrial bioenergetics assay suggested that 54, 55, and 64 enhanced the oxidative phosphorylation in cancer cells, which might contribute to the observed anti-proliferation effects. Collectively, these results suggested that 54, 55, and 64 could be promising compounds for the development of potent PDK1 inhibitors.

Approach for the direct synthesis of β-dichlorosubstituted acetanilides using iodine trichloride (ICl3) as the oxidant and catalyst

A reliable method for direct synthesis of β-dichlorosubstituted acetanilides is reported. The key transformation involves the oxidative and catalytic cleavage of a carbon-carbon bond in the presence of iodine trichloride (ICl3). In this protoco

Divergent synthesis of α,α-dihaloamides through α,α-dihalogenation of β-oxo amides by using N-halosuccinimides

An efficient and divergent one-pot synthesis of α,α- dihaloamides from readily available β-oxo amides based on the selection of reaction conditions is reported. α,α-Dihalo-β-oxo amides were produced by treating β-oxo amides with N-chlorosuccinimide (NCS) or N-bromosuccinimide (NBS) in water at room temperature, whereas α,α-dihaloacetamides were synthesized by subjecting β-oxo amides to NCS or NBS in ethanol under reflux. A divergent synthesis of α,α-dihalo-β-oxo amides and α,α-dihaloacetamides has been developed from readily available β-oxo amides. Upon treatment with N-halosuccinimides in water at room temperature, α,α-dihalo-β- oxo amides were produced, whereas dihaloacetamides were synthesized by treatment of β-oxo amides with N-halosuccinimides in ethanol under reflux. Copyright

Organic synthesis using (diacetoxyiodo)benzene (DIB): Unexpected and novel oxidation of 3-oxobutanamides to 2,2-dihalo-N-phenylacetamides

A novel and reliable method for the direct preparation of 2,2-dihalo-N-phenylacetamides is reported. The key transformation involves the cleavage of a carbon-carbon bond in the presence of DIB and a Lewis acid as the halogen source, and thus this method s

Novel N-phenyl dichloroacetamide derivatives as anticancer reagents: Design, synthesis and biological evaluation

A current study shows that sodium dichloroacetate (DCA) can induce cancer cell apoptosis and inhibit tumor growth, but its cytotoxic activity is low (IC50 > 1000 μM for A549). In this paper, a variety of DCA derivatives were synthesized, and their cytotoxic activities were evaluated. The result showed that the N-phenyl-2,2-dichloroacetamide analogues had satisfactory potencies. Among them, N-(3-iodophenyl)-2,2-dichloroacetamide (3e), an optimized lead compound, has an IC50 against A549 as low as 4.76 μM. Furthermore, it can induce cancer cell apoptosis and has a low toxicity in mice (LD50 = 1117 mg/kg). N-phenyl-2,2-dichloroacetamide analogues has higher cytotoxic activity and N-(3-iodophenyl)-2,2-dichloroacetamide (3e) is an optimized lead compound.

Substituent effect on the infrared and Raman spectra of N-(substituted-phenyl)-2,2-dichloroacetamides, XyC6H 5-yNHCOCHCl2 (X = o/m/p-CH3 or Cl; y = 1, 2 or 3)

Several substituted N-(phenyl)-2,2-dichloroacetamides of the configuration XyC6H5-yNHCOCHCl2 (where, X = H, CH3 or Cl and y = 1, 2 or 3) have been synthesized and their infrared and Raman spectra measured in the solid state with the objective of correlating CO and NH frequencies of these substituted phenyldichloroacetamides with those of substituted phenylchloroacetamides and trichloroacetamides. The study reveals that there is no systematic variation in the frequencies with the substitution. The effect of substitution in the phenyl ring in terms of electron-donating and electron-withdrawing groups could not be generalized. The same trend is observed even with disubstituted phenyl-2,2-dichloroacetamides, which may be due to the varying crystalline states of the amides as the spectra are measured in the solid state. The infrared and Raman frequencies of the amides of the configuration XyC6H5-yNHCOR (where, X = H, CH3 or Cl and y = 1, 2 or 3 and R = CH2Cl, CHCl2, CCl3) have also been examined for comparison purpose. The entire data indicate that neither the infrared CO or NH absorption frequencies nor the Raman scattered CO or NH frequencies show regular trends in all these compounds for the stated above.