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4252-78-2

4252-78-2

Identification

Synonyms:Acetophenone,2,2',4'-trichloro- (6CI,7CI,8CI);2,4,2'-Trichloroacetophenone;2,4-Dichlorophenacyl chloride;2-Chloro-1-(2,4-dichlorophenyl)ethanone;2-Chloro-1-(2',4'-dichlorophenyl)ethanone;Chloromethyl 2,4-dichlorophenylketone;a,2,4-Trichloroacetophenone;w-Chloro-2,4-dichloroacetophenone;

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Safety information and MSDS view more

  • Pictogram(s):IrritantXi,CorrosiveC,DangerousN, ToxicT

  • Hazard Codes:Xi,C,N,T

  • Signal Word:Danger

  • Hazard Statement:H302 Harmful if swallowedH314 Causes severe skin burns and eye damage H317 May cause an allergic skin reaction H318 Causes serious eye damage H400 Very toxic to aquatic life H410 Very toxic to aquatic life with long lasting effects

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician. SYMPTOMS: Symptoms of exposure to this compound include corrosion and lachrymation. Inhalation may be fatal as a result of spasm, inflammation and edema of the larynx and bronchi, chemical pneumonitis and pulmonary edema. Other symptoms include burning sensation, coughing, wheezing, laryngitis, shortness of breath, headache, nausea and vomiting. ACUTE/CHRONIC HAZARDS: This compound is a corrosive and a lachrymator. It is harmful by ingestion, inhalation or skin absorption. It is extremely destructive to tissue of the mucous membranes and upper respiratory tract, eyes and skin. When heated to decomposition it emits toxic fumes of carbon monoxide, carbon dioxide and hydrogen chloride gas.

  • Fire-fighting measures: Suitable extinguishing media Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. This chemical is probably combustible. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price

  • Manufacture/Brand
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  • Manufacture/Brand:TRC
  • Product Description:α,2,4-Trichloroacetophenone
  • Packaging:50g
  • Price:$ 150
  • Delivery:In stock
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  • Manufacture/Brand:TRC
  • Product Description:α,2,4-Trichloroacetophenone
  • Packaging:100g
  • Price:$ 250
  • Delivery:In stock
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  • Manufacture/Brand:TCI Chemical
  • Product Description:2,2',4'-Trichloroacetophenone >98.0%(GC)
  • Packaging:250g
  • Price:$ 241
  • Delivery:In stock
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  • Manufacture/Brand:TCI Chemical
  • Product Description:2,2',4'-Trichloroacetophenone >98.0%(GC)
  • Packaging:25g
  • Price:$ 43
  • Delivery:In stock
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:2,4-Dichlorophenacyl chloride
  • Packaging:500 g
  • Price:$ 112
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:2,4-Dichlorophenacyl chloride
  • Packaging:100 g
  • Price:$ 29
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:2,2′,4′-Trichloroacetophenone 97%
  • Packaging:25g
  • Price:$ 38.5
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  • Manufacture/Brand:Medical Isotopes, Inc.
  • Product Description:α,2,4-Trichloroacetophenone
  • Packaging:100 g
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:2,2',4'-Trichloroacetophenone 95+%
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:2,2',4'-Trichloroacetophenone 95+%
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Relevant articles and documentsAll total 18 Articles be found

Chalcone-Benzotriazole Conjugates as New Potential Antimicrobial Agents: Design, Synthesis, Biological Evaluation and Synergism with Clinical Drugs

Liu, Hanbo,Gopala, Lavanya,Avula, Srinivasa Rao,Jeyakkumar, Ponmani,Peng, Xinmei,Zhou, Chenghe,Geng, Rongxia

, p. 483 - 496 (2017)

A series of chalcone-benzotriazole conjugates as new potential antimicrobial agents were synthesized and characterized by 1H NMR, 13C NMR, IR and HRMS spectra. Antimicrobial assay manifested that some target compounds gave moderate to good antibacterial and antifungal activities. The N-1 derived benzotriazole 5e and N-2 derived benzotriazole 6a exhibited valuable inhibitory efficacy against some tested strains. Especially, derivative 6a gave superior antifungal efficacies against C. utilis, S. cerevisiae and A. flavus (MIC=0.01, 0.02, 0.02 μmol/mL, respectively) to Fluconazole. The drug combination of compound 5e or 6a with antibacterial Chloromycin, Norfloxacin and antifungal Fluconazole respectively showed stronger antimicrobial efficiency with less dosage and broader antimicrobial spectrum than their separated use alone. The preliminary interaction with calf thymus DNA revealed that compound 6a could intercalate into DNA to form 6a-DNA supramolecular complex which might be a factor to exert its powerful bioactivity. Molecular docking study indicated strong binding of compound 6a with DNA gyrase. The structural parameters such as molecular orbital energy and molecular electrostatic potential of compound 6a were also investigated, which provided better understanding for its good antimicrobial activity.

Lead optimization generates selenium-containing miconazole CYP51 inhibitors with improved pharmacological profile for the treatment of fungal infections

Xu, Hang,Yan, Zhong-zuo,Guo, Meng-bi,An, Ran,Wang, Xin,Zhang, Rui,Mou, Yan-hua,Hou, Zhuang,Guo, Chun

, (2021/03/16)

A series of selenium-containing miconazole derivatives were identified as potent antifungal drugs in our previous study. Representative compound A03 (MIC = 0.01 μg/mL against C.alb. 5314) proved efficacious in inhibiting the growth of fungal pathogens. However, further study showed lead compound A03 exhibited potential hemolysis, significant cytotoxic effect and unfavorable metabolic stability and was therefore modified to overcome these drawbacks. In this article, the further optimization of selenium-containing miconazole derivatives resulted in the discovery of similarly potent compound B17 (MIC = 0.02 μg/mL against C.alb. 5314), exhibiting a superior pharmacological profile with decreased rate of metabolism, cytotoxic effect and hemolysis. Furthermore, compound B17 showed fungicidal activity against Candida albicans and significant effects on the treatment of resistant Candida albicans infections. Meanwhile, compound B17 not only could reduce the ergosterol biosynthesis pathway by inhibiting CYP51, but also inhibited biofilm formation. More importantly, compound B17 also shows promising in vivo efficacy after intraperitoneal injection and the PK study of compound B17 was evaluated. In addition, molecular docking studies provide a model for the interaction between the compound B17 and the CYP51 protein. Overall, we believe that these selenium-containing miconazole compounds can be further developed for the potential treatment of fungal infections.

Design, synthesis, and biological evaluation of novel miconazole analogues containing selenium as potent antifungal agents

An, Ran,Guo, Chun,Guo, Meng-bi,Hou, Zhuang,Mou, Yan-hua,Su, Xin,Xu, Hang

, (2020/05/11)

Herein, based on the theory of bioisosterism, a series of novel miconazole analogues containing selenium were designed, synthesized and their inhibitory effects on thirteen strains of pathogenic fungi were evaluated. It is especially encouraging that all the novel target compounds displayed significant antifungal activities against all tested strains. Furthermore, all the target compounds showed excellent inhibitory effects on fluconazole-resistant fungi. Subsequently, preliminary mechanistic studies indicated that the representative compound A03 had a strong inhibitory effect on C.alb. CYP51. Moreover, the target compounds could prevent the formation of fungi biofilms. Further hemolysis test verified that potential compounds had higher safety than miconazole. In addition, molecular docking study provided the interaction modes between the target compounds and C.alb. CYP51. These results strongly suggested that some target compounds are promising as novel antifungal drugs.

Novel triazole derivatives containing different ester skeleton: Design, synthesis, biological evaluation and molecular docking

Han, Xiaoyan,Ren, Liwen,Song, Yali,Sun, Xiaoyang,Wang, Jinhua,Wang, Shumin,Xiao, Bin,Zhang, Na

, p. 64 - 69 (2020/02/03)

Invasive fungal disease constitutes a growing health problem and development of novel antifungal drugs with high potency and selectivity are in an urgent need. In this study, a novel series of triazole derivatives containing different ester skeleton were designed and synthesized. Microdilution broth method was used to investigate antifungal activity. Significant inhibitory activity of compounds 5c, 5d, 5e, 5f, 5m and 5n was evaluated against the Candida albicans (I), Candida albicans clinical isolate (II), Candida glabrata clinical isolate (I), and Candida glabrata (II) with minimum inhibitory concentrations (MIC80) values ranging from 2 to 16μg/mL. Notably, compounds 5e and 5n showed the best inhibition against Candida albicans (II), Candida glabrata (I), and Candida glabrata (II) at the concentrations of 2 and 8μg/mL, respectively. Molecular docking study revealed that the target compounds interacted with CYP51 mainly through hydrophobic and van der Waals interactions. The results indicated that these novel triazole derivatives could serve as promising leads for development of antifungal agents.

A new exploration towards aminothiazolquinolone oximes as potentially multi-targeting antibacterial agents: Design, synthesis and evaluation acting on microbes, DNA, HSA and topoisomerase IV

Wang, Liang-Liang,Battini, Narsaiah,Bheemanaboina, Rammohan R. Yadav,Ansari, Mohammad Fawad,Chen, Jin-Ping,Xie, Yun-Peng,Cai, Gui-Xin,Zhang, Shao-Lin,Zhou, Cheng-He

, p. 166 - 181 (2019/07/02)

This work did a new exploration towards aminothiazolquinolone oximes as potentially multi-targeting antimicrobial agents. A class of novel hybrids of quinolone, aminothiazole, piperazine and oxime fragments were designed for the first time, conveniently synthesized as well as characterized by 1H NMR, 13C NMR and HRMS spectra. Biological activity showed that some of the synthesized compounds exhibited good antimicrobial activities in comparison with the reference drugs. Especially, O-methyl oxime derivative 10b displayed excellent inhibitory efficacy against MRSA and S. aureus 25923 with MIC values of 0.009 and 0.017 mM, respectively. Further studies indicated that the highly active compound 10b showed low toxicity toward BEAS-2B and A549 cell lines and no obvious propensity to trigger the development of bacterial resistance. Quantum chemical studies have also been conducted and rationally explained the structural features essential for activity. The preliminarily mechanism exploration revealed that compound 10b could not only exert efficient membrane permeability by interfering with the integrity of cells, bind with topoisomerase IV–DNA complex through hydrogen bonds and π-π stacking, but also form a steady biosupramolecular complex by intercalating into DNA to exert the efficient antibacterial activity. The supramolecular interaction between compound 10b and human serum albumin (HSA) was a static quenching, and the binding process was spontaneous, where hydrogen bonds and van der Waals force played vital roles in the supramolecular transportation of the active compound 10b by HSA.

Method for synthesizing azaconazole through 4-amino-4H-1,2,4-triazole alkylation

-

, (2018/11/03)

The invention discloses a method for synthesizing azaconazole through 4-amino-4H-1,2,4-triazole alkylation. The method comprises step 1, preparing a raw material which is shown in a following image; step 2, synthesizing 1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazole-1-yl) ethanone; step 3, synthesizing azaconazole. The method disclosed by the invention has the advantages that development of a novel azaconazole bactericide successfully fills the blank in China, synthesis researches of similar derivatives based on the azaconazole bactericide will be in the ascendant, and successful development andindustrial implementation of varieties of novel bactericides have a far-reaching influence on national economy development. The method disclosed by the invention is an azaconazole synthesizing method.

Process route upstream and downstream products

Process route

chloroacetyl chloride
79-04-9

chloroacetyl chloride

1,3-Dichlorobenzene
541-73-1

1,3-Dichlorobenzene

2,2',4'-trichloroacetophenone
4252-78-2

2,2',4'-trichloroacetophenone

Conditions
Conditions Yield
With aluminum (III) chloride; at 30 ℃; for 3h;
93.1%
With aluminum (III) chloride; In dichloromethane; at 20 ℃;
90%
With aluminum (III) chloride; In dichloromethane; for 3h; Reflux;
86%
With aluminum (III) chloride; In dichloromethane; for 4h; Reflux;
80%
With carbon disulfide; aluminium trichloride;
With aluminium trichloride; In dichloromethane;
With aluminum (III) chloride; In dichloromethane;
With aluminum (III) chloride; In dichloromethane; at 20 ℃;
With aluminum (III) chloride; In dichloromethane; for 8h; Solvent;
With aluminum (III) chloride; In dichloromethane; at 20 ℃;
1,3-Dichlorobenzene; With aluminum (III) chloride; In 1,2-dichloro-ethane; at 30 ℃; for 0.5h;
chloroacetyl chloride; In 1,2-dichloro-ethane; at 0 - 20 ℃; for 25h;
at 20 ℃; for 20h;
With aluminum (III) chloride;
1-(2,4-dichlorophenyl)ethan-1-one
2234-16-4

1-(2,4-dichlorophenyl)ethan-1-one

2,2-dichloro-1-(2,4-dichlorophenyl)ethan-1-one
2274-66-0

2,2-dichloro-1-(2,4-dichlorophenyl)ethan-1-one

2,2',4'-trichloroacetophenone
4252-78-2

2,2',4'-trichloroacetophenone

Conditions
Conditions Yield
With chloro-trimethyl-silane; potassium nitrate; In dichloromethane; at 60 ℃; for 16h;
73%
Chloroacetamide
79-07-2

Chloroacetamide

1,3-Dichlorobenzene
541-73-1

1,3-Dichlorobenzene

2,2',4'-trichloroacetophenone
4252-78-2

2,2',4'-trichloroacetophenone

Conditions
Conditions Yield
With potassium chloride; tin(ll) chloride; at 65 ℃; for 5h; Temperature; Concentration;
93%
chloroacetyl chloride
79-04-9

chloroacetyl chloride

1,2-dichloro-benzene
95-50-1

1,2-dichloro-benzene

2,2',4'-trichloroacetophenone
4252-78-2

2,2',4'-trichloroacetophenone

Conditions
Conditions Yield
With aluminum (III) chloride; at 30 - 50 ℃;
88.5%
1-(2,4-dichlorophenyl)ethan-1-one
2234-16-4

1-(2,4-dichlorophenyl)ethan-1-one

2,2',4'-trichloroacetophenone
4252-78-2

2,2',4'-trichloroacetophenone

Conditions
Conditions Yield
With chlorine;
With aluminum (III) chloride; chlorine; In diethyl ether; Cooling with ice;
Phosphorsaeure-<2-chlor-1-(2,4-dichlor-phenyl)-vinylester>-diisopropylester
15289-81-3

Phosphorsaeure-<2-chlor-1-(2,4-dichlor-phenyl)-vinylester>-diisopropylester

2,2',4'-trichloroacetophenone
4252-78-2

2,2',4'-trichloroacetophenone

Conditions
Conditions Yield
With toluene-4-sulfonic acid;
With sulfuric acid; at 165 ℃;
With toluene-4-sulfonic acid; at 165 ℃;
2,4-dichloro-α-methylbenzyl alcohol
1475-13-4,415679-40-2

2,4-dichloro-α-methylbenzyl alcohol

2,2',4'-trichloroacetophenone
4252-78-2

2,2',4'-trichloroacetophenone

Conditions
Conditions Yield
With hydrogenchloride; 3-chloro-benzenecarboperoxoic acid; In N,N-dimethyl-formamide; at 25 ℃; for 6h;
92 % Chromat.
1,3-Dichlorobenzene
541-73-1

1,3-Dichlorobenzene

2,2',4'-trichloroacetophenone
4252-78-2

2,2',4'-trichloroacetophenone

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1.1: aluminum (III) chloride / 1,2-dichloro-benzene / 0.33 h
1.2: Cooling with ice
2.1: aluminum (III) chloride; chlorine / diethyl ether / Cooling with ice
With aluminum (III) chloride; chlorine; In diethyl ether; 1,2-dichloro-benzene;
2,2-dichloro-1-(2,4-dichlorophenyl)ethan-1-one
2274-66-0

2,2-dichloro-1-(2,4-dichlorophenyl)ethan-1-one

2,2',4'-trichloroacetophenone
4252-78-2

2,2',4'-trichloroacetophenone

Conditions
Conditions Yield
Multi-step reaction with 2 steps
2: TsOH / 165 °C
With toluene-4-sulfonic acid;
aluminium trichloride
7446-70-0

aluminium trichloride

chloroacetyl chloride
79-04-9

chloroacetyl chloride

1,3-Dichlorobenzene
541-73-1

1,3-Dichlorobenzene

2,2',4'-trichloroacetophenone
4252-78-2

2,2',4'-trichloroacetophenone

Conditions
Conditions Yield

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  • Amadis Chemical Co., Ltd.
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  • COLORCOM LTD.
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  • Contact Tel:+86-571-89007001
  • Emails:medkem@medkem.cn
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  • Shaanxi BLOOM TECH Co.,Ltd
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  • Chemwill Asia Co., Ltd.
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  • Hangzhou Ocean Chemical Co., Ltd.
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