2965-17-5

Usage

Uses

Used in Pharmaceutical Industry:
(2-fluorophenoxy)acetyl chloride is used as an intermediate for the synthesis of various pharmaceuticals due to its reactive nature, which allows for the creation of a wide range of medicinal compounds.
Used in Pesticide Industry:
(2-fluorophenoxy)acetyl chloride is used as a chemical intermediate in the production of pesticides, contributing to the development of effective crop protection agents.
Used in Organic Compounds Synthesis:
(2-fluorophenoxy)acetyl chloride is utilized as a building block in the synthesis of various organic compounds, owing to its ability to readily participate in chemical reactions.
Precautions:
Due to its reactivity and potential health hazards, (2-fluorophenoxy)acetyl chloride should be handled with care. It is important to store and use it in a well-ventilated area and with appropriate safety equipment to prevent harm to human health and the environment.

Upstream product

• 348-10-7 (2-fluorophenoxy)acetic acid 
• 367-12-4 2-fluorophenol 
• 79-11-8 chloroacetic acid 
• 2248-56-8 ethyl 2-(4-fluorophenoxy)acetate 

Downstream Products

• 904702-63-2 C₁₆H₁₇FNO₅P 
• 866146-00-1 O,O-dimethyl α-(2-fluorophenoxyacetoxy)ethylphosphonate 
• 904702-68-7 O-methyl [(2-(2-fluorophenoxy)acetoxy)(2-chlorophenyl)methyl]methylphosphinate 
• 904702-69-8 O-methyl [(2-(2-fluorophenoxy)acetoxy)(4-fluorophenyl)methyl]methylphosphinate 
• 1395103-28-2 2-(2-fluorophenoxyacetoxy)(phenyl)methyl-5,5-dimethyl-1,3,2-dioxaphosphinan-2-one 
• 1395103-23-7 2-[(2-fluorophenoxy)acetoxy](furan-2-yl)methyl-5,5-dimethyl-1,3,2-dioxaphosphinan-2-one 
• 1031434-74-8 C₂₃H₁₉FN₂O₃ 

Relevant academic research and scientific papers

Herbicidal activity and application cyclic of phosphonates

Among alkylphosphonates Io,O,O-dimethyl 1-(2,4-dichlorophenoxyacetoxy) ethylphosphonate (clacyfos) was found to be an effective inhibitor against dicotyledons PHDc and exhibited excellent herbicidal activity in our previous work. According to our study on the alkylphosphonates Io, both R1 and R2 groups in the structural unit of phosphorus-containing played a very important role in herbicidal activity. Therefore, a series of 2-[1-(substituted phenoxycarboxy)alkyl]-5,5-dimethyl-1,3,2-dioxaphosphinane-2-one containing fluorine II was obtained by the modification of alkylphosphonates Io. The bioassay results showed that cyclic phosphonate II-6 with CH3 as R, 2-Cl,4-F as Yn exhibited promising herbicidal activity. Its herbicidal activity, weed-controlling spectrum, selectivity between crops and weeds were further evaluated in greenhouse and field.

Synthesis and Biological Activity of 4-[(Substituted Phenoxyacetoxy)methyl]-2,6,7-trioxa-1-phosphabicyclo[2.2.2]octane-1-one

A series of novel 4-[(substituted phenoxyacetoxy)methyl]-2,6,7-trioxa-1-phosphabicyclo[2.2.2]octane-1-one 4a, 4b, 4c, 4d, 4e, 4f, 4g, 4h, 4i, 4j, 4k, 4l, 4m, 4n, 4o were synthesized. Their structures were confirmed by IR,1H NMR, mass spectroscopy, and elemental analyses. The results of preliminary bioassays show that some of the title compounds exhibit moderate to good herbicidal and fungicidal activities. For example, the title compounds 4b, 4c, 4f, 4h, 4i, and 4j possess 90–100% inhibition against the growth of roots of both rape and barnyard grass at 10 mg/L. Moreover, the title compounds 4f, 4g, and 4h possess 75–89% inhibition against Botrytis cinerea at the concentration of 50 mg/L.

Privileged 1,2,4-oxadiazoles in anticancer drug design: Novel 5-aryloxymethyl-1,2,4-oxadiazole leads for prostate cancer therapy

Based on the structure of the previously identified leads, new series of compounds containing 1,2,4-oxadiazole core was designed. A small, diverse library of 51 compounds including both 2-(acylamino)ethyl and 2-ureidoethyl side chains was synthesized using parallel chemistry and tested for antiproliferative activity against prostate cancer DU-145 cell line. Four hit compounds - all belonging to 2-ureidoethyl series - were identified and three compounds were confirmed as 10-20 μM inhibitors. The similarity in compounds' periphery and the data obtained previously suggest a similar mode of action for these compounds which was postulated as tubulin inhibition and was confirmed by in silico docking. These data provide further evidence for the privileged character of 1,2,4-oxadiazoles in antiproliferative compound design.

Synthesis and Biological Activity of Ethyl 4-Alkyl-2-(2-(substituted phenoxy)acetamido)thiazole-5-carboxylate

(Chemical Equation Presented) A series of novel ethyl 4-(methyl or trifluoromethyl)-2-(2-(substituted phenoxy)acetamido)thiazole-5-carboxylates 7a, 7b, 7c, 7d, 7e and 8f, 8g, 8h, 8i, 8j, 8k, 8l, 8m, 8n, 8o, 8p, 8q, 8r were synthesized, and their structures were confirmed by IR, 1H-NMR, MS spectra and elemental analysis. The results of preliminary bioassays show that some of the title compounds exhibit moderate to good herbicidal activities. Compared with the fluorine free compounds 7a, 7b, and 7e, the compounds bearing fluorine 8g, 8j, and 8q showed higher herbicidal activities with 70-100% inhibition against Capsella bursa-pastoris, Amaranthus restroflexus, and Eclipta prostrata at the dosage of 150 g/ha, which indicated that the trifluoromethyl on the thiazole ring was beneficial for the herbicidal activity. Furthermore, compounds 8f, 8g, 8h, 8i, 8j, 8k, 8l, 8m, 8n, 8o, 8p, 8q, 8r were tested for fungicidal activity against Pseudoperonospora cubensis at 500 μg/mL. Compounds 8f and 8q showed the best fungicidal activity with more than 80% inhibition.

Synthesis and Herbicidal Activities of Sodium Methyl(α-(Substituted Phenoxyacetoxy)Alkyl)Phosphinates

A series of sodium methyl(α-(substituted phenoxyacetoxy)alkyl)phosphinates was designed and synthesized. Their structures were confirmed by IR, 1H NMR and elemental analysis, and some of them were further confirmed by MS. The results of bioassay showed that most of title compounds exhibited moderate to good herbicidal activities against the root of barnyard grass and rape at 10～100 mg/L.

Synthesis and biological activity of 1-(Substituted phenoxyacetoxy)- 1-(pyridin-2-yl or thien-2-yl)methylphosphonates

A series of novel O,O-dimethyl 1-(substituted phenoxyacetoxy)-1-(pyridin-2-yl or thien-2-yl)methylphosphonates 6a-n and 7a-d were synthesized. Their structures were confirmed by IR, 1H NMR, mass spectroscopy, and elemental analyses. The results of preliminary bioassays show that some of the title compounds exhibit moderate to good herbicidal and fungicidal activities. For example, the title compounds 6a, 6c, 6l, 6m, and 7d possess 90-100% inhibition against most of the tested plants at the dosage of 1500 g ai/ha, whereas the title compounds 6b, 6g-h and 6n possess 92-100% inhibition against Fusarium oxysporum, Phyricularia grisea, Botrytis cinereapers, Gibberella zeae, Sclerotinia sclerotiorum, and Cercospora beticola at the concentration of 50mg/L.

Synthesis and Biological Activity of O-Methyl Methyl 1-(Substituted Phenoxyacetoxy)-1-(thien-2-yl)methylphosphinates

A series of novel O-methyl methyl 1-(substituted phenoxyacetoxy)-1-(thien-2-yl)methylphosphinates 5a, 5b, 5c, 5d, 5e, 5f, 5g, 5h were synthesized. Their structures were confirmed by IR, 1H NMR, mass spectroscopy, and elemental analyses. The results of preliminary bioassays show that some of the title compounds exhibit moderate to good herbicidal and fungicidal activities. For example, the title compounds 5c, 5d, and 5g possess 90-100% inhibition against the tested plants at the concentration of 10 mg/L and 100 mg/L, whereas the title compounds 5a, 5b, 5c, and 5h possess 70-94% inhibition against Phyricularia grisea and Sclerotinia sclerotiorum at the concentration of 50 mg/L.

Synthesis, biological evaluation, and structure-activity relationships of potent noncovalent and nonpeptidic cruzain inhibitors as anti-Trypanosoma cruzi agents

The development of cruzain inhibitors has been driven by the urgent need to develop novel and more effective drugs for the treatment of Chagas' disease. Herein, we report the lead optimization of a class of noncovalent cruzain inhibitors, starting from an inhibitor previously cocrystallized with the enzyme (Ki = 0.8 μM). With the goal of achieving a better understanding of the structure-activity relationships, we have synthesized and evaluated a series of over 40 analogues, leading to the development of a very promising competitive inhibitor (8r, IC50 = 200 nM, Ki = 82 nM). Investigation of the in vitro trypanocidal activity and preliminary cytotoxicity revealed the potential of the most potent cruzain inhibitors in guiding further medicinal chemistry efforts to develop drug candidates for Chagas' disease.

Synthesis and herbicidal activity of [(Substituted Phenoxyacetoxy) (Substituted Phenyl)Methyl](Methyl) phosphinates containing fluorine

A series of [(substituted phenoxyacetoxy)(substituted phenyl)methyl] (methyl)phos- phinates containing fluorine were designed and synthesized. All the synthesized compounds were identified by elemental analysis, IR, 1H NMR, mass spectrometry. O-methyl [(2-fluorophenoxyacetoxy)(2,4- dichlorophenyl)methyl](methyl)phosphinate was further analyzed by X-ray single-crystal diffraction. Their herbicidal activity against a set of weed species was examined. Some of the compounds showed potential herbicidal activity, which provided some indications for further studies on structure modification. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.

Synthesis and herbicidal activity of 2-(substituted phenoxyacetoxy)alkyl-5, 5-dimethyl-1,3,2-dioxaphosphinan-2-one containing fluorine

A series of novel 2-(substituted phenoxyacetoxy)alkyl-5,5-dimethyl-1,3,2- dioxaphosphinan-2-one bearing fluorine 5a-n and fluorine free 5o-q were designed and synthesized. The results of bioassay showed that some of the target compounds exhibited excellent herbicidal activities to Abutilon theophrasti, Brassica juncea, Amaranthus retroflexus and Eclipta prostrata in post-emergence treatment at a dosage of 150 g ai/ha. It could be found that the type and position of fluorine-containing group as X or Y on benzene ring had a very important effect on herbicidal activity. Compound 5l 2-[(2-chloro-4- fluorophenoxy)acetoxy](methyl)methyl-5,5-dimethyl-1,3,2-dioxaphosphinan-2-one showed notable herbicidal activity, with 100% inhibition against A. theophrasti and A. retroflexus; and compound 5m 2-(3-trifluoromethylphenoxyacetoxy)(methyl) methyl-5,5-dimethyl-1,3,2-dioxaphosphinan-2-one with 100% inhibition against A. theophrasti even at a dosage of 75 g ai/ha. Additional crop selectivity testing showed that compounds 5g 2-(3-trifluoromethylphenoxyacetoxy)(phenyl)methyl-5,5- dimethyl-1,3,2-dioxaphosphinan-2-one and 5l are safe to rice, corn, cotton, rape and wheat.