39784-11-7

Usage

Uses

Used in Pharmaceutical Synthesis:
(4-chloro-3-methylphenoxy)acetyl chloride is used as a reactant in the pharmaceutical industry for the synthesis of various drugs. Its unique chemical structure allows it to serve as an intermediate in the development of new medications, contributing to the advancement of pharmaceutical research and drug discovery.
Used in Agrochemical Production:
In the agrochemical industry, (4-chloro-3-methylphenoxy)acetyl chloride is utilized as an intermediate in the production of pesticides and other agricultural chemicals. Its reactivity and versatility make it a valuable component in the formulation of effective and targeted agrochemicals to improve crop protection and yield.
Safety Precautions:
Due to its highly reactive and corrosive nature, (4-chloro-3-methylphenoxy)acetyl chloride requires careful handling and the implementation of appropriate safety measures. This includes the use of personal protective equipment, proper ventilation, and adherence to safety guidelines to prevent harm to health and the environment.

Upstream product

• 588-20-5 4-chloro-3-methylphenoxyacetic acid 
• 59-50-7 4-Chloro-3-methylphenol 

Downstream Products

• 20895-59-4 β-<3-Methyl-4-chlor-phenoxy>-acetophenon 
• 650614-57-6 2-[2-(4-chloro-3-methyl-phenoxy)-acetylamino]-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid ethyl ester 
• 302803-48-1 2-[2-(4-chloro-3-methyl-phenoxy)-acetylamino]-4,5-dimethyl-thiophene-3-carboxylic acid ethyl ester 
• 900502-09-2 C₁₇H₁₉ClNO₅P 
• 429626-39-1 1-[(4-chloro-3-methylphenoxy)-acetyl]-4-(2-pyridyl)-piperazine 
• 429628-30-8 1-[(4-chloro-3-methylphenoxy)-acetyl]-4-(2-methoxyphenyl)-piperazine 
• 904702-54-1 O,O-dimethyl α-(3-methyl-4-chlorophenoxyacetoxy)-3-nitrobenzylphosphonate 
• 1392226-22-0 2-[((4-chloro-3-methylphenoxy)acetyl)oxy](methyl)methyl-5,5-dimethyl-1,3,2-dioxaphosphinan-2-one 
• 1392226-18-4 2-[((4-chloro-3-methylphenoxy)acetyl)oxy](phenyl)methyl-5,5-dimethyl-1,3,2-dioxaphosphinan-2-one 
• 1392226-10-6 2-[((4-chloro-3-methylphenoxy)acetyl)oxy](furan-2-yl)methyl-5,5-dimethyl-1,3,2-dioxaphosphinan-2-one 
• 1357284-67-3 O,O'-dimethyl {[2-(3-methyl-4-chlorophenoxy)acetamido](4-methylphenyl)methyl}phosphonate 
• 68720-31-0 3-methyl-4-chlorophenoxyacetic acid anilide 
• 1026585-67-0 2-(4-chloro-3-methyl-phenoxy)-N-(3-hydrazinocarbonyl-4,5,6,7-tetrahydro-benzo[b]thiophen-2-yl)-acetamide 
• 1027936-94-2 2-(4-chloro-3-methyl-phenoxy)-N-(3-hydrazinocarbonyl-4,5-dimethyl-thiophen-2-yl)-acetamide 

Relevant academic research and scientific papers

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.

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 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 and herbicidal activity of 2-(Substituted phenoxyacetoxy)alkyl-5, 5-dimethyl-1,3,2-dioxaphosphinan-2-one

A series of 2-(substituted phenoxyacetoxy)alkyl-5,5-dimethyl-1,3,2- dioxaphosphinan-2-ones IIa-s were designed and synthesized on the basis of the previous work for the modification of alkylphosphonates I, and their structures were confirmed by 1H NMR, 31P NMR, 13C NMR, IR, MS, and elemental analysis. Their herbicidal activities against seven species of weeds were evaluated in a greenhouse. A part of the title compounds such as IIa-g, IIk, IIo, and IIr exhibited significant postemergence herbicidal activity against Abutilon theophrasti, Brassica juncea, Amaranthus retroflexus, and Eclipta prostrate at a dosage of 150 g ai/ha. Structure-activity relationship analyses indicated that the introduction of a phosphorus-containing heterocyclic ring had a favorable effect on herbicidal activity, and their herbicidal activity could be further increased by a reasonable combination of X, Y, and R in parent structure II. It could be found that the title compounds IIa 2-[(2,4-dichlorophenoxy)acetoxy](methyl)methyl-5,5-dimethyl-1,3, 2-dioxaphosphinan-2-one and IIr 2-[(4-chloro-2-methyl-phenoxy)acetoxy](methyl) methyl-5,5-dimethyl-1,3,2-dioxaphosphinan-2-one possess high activity and a broad spectrum against all of the test broadleaf weeds with 70-100% inhibition effect at a dosage of 75 g ai/ha, and the title compounds IIa and IIr are safe for corn and wheat at a dosage of 150 g ai/ha. Furthermore, the title compound IIa possesses low rat toxicity. These results suggest that the title compounds IIa and IIr could be potential and selective postemergence herbicides for further development.

Studies of O,O-Dimethyl α-(2,4-Dichlorophenoxyacetoxy) ethylphosphonate (HW02) as a new herbicide. 1. Synthesis and herbicidal activity of HW02 and analogues as novel inhibitors of pyruvate dehydrogenase complex

On the basis of the previous work for optimization of O,O-diethyl α-(substituted phenoxyacetoxy)alkylphosphonates, further extensive syntheticmodifications were made to the substituents in alkylphosphonate and phenoxymoieties of the title compounds. New O,O-dimethyl α-(substituted phenoxyacetoxy)alkylphosphonates were synthesized as potential inhibitors of pyruvate dehydorogenase complex (PDHc). Their herbicidal activity and efficacy in vitro against PDHc were examined. Some of these compounds exhibited significant herbicidal activity and were demonstrated to be effective inhibitors of PDHc from three different plants. The structure-activity relationships of these compounds including previously reported analogous compoundswere studied by examining their herbicidal activities. Both inhibitory potency against PDHc and herbicidal activity of title compounds could be increased greatly by optimizing substituent groups of the title compounds. O,O-Dimethyl α-(2,4- dichlorophenoxyacetoxy)ethylphosphonate (I-5), which acted as a competitive inhibitor of PDHc with much higher inhibitory potency against PDHc from Pisum sativum and Phaseolus radiatus than from Oryza sativa, was found to be themost effective compound against broadleaf weeds and showed potential utility as herbicide.

Synthesis and biological activity of α-oxo-2-pyridyl methyl phosphinates

In an attempt to discover novel compounds with high activity and low toxicity, a series of new O,O-dimethyl-α-(substituted phenoxyacetoxy)-2- pyridyl methyl phosphinates, 5a-5h, have been designed and synthesized by the reaction of substituted phenoxyacetic chloride with 1-hydroxy-2-pyridyl methyl phosphinate, The structures of all new compounds were characterized by elementary analysis, IR, 1H NMR, and MS spectroscopies. The results of preliminary bioassay indicate that most of the target compounds have excellent inhibitory activities on barnyard grass and rape. Copyright Taylor & Francis Group, LLC.

Design, synthesis and antihistaminic (H1) activity of some condensed 3- aminopyrimidin-4(3H)-ones

A novel series of condensed 3-amino-2-(substituted)methylpyrimidin- 4(3H)-ones is reported with potential H1 receptor antagonistic activity. The IC50 values for 23 compounds were found to be in the micromolar range. Five lead compounds (10c, e, g, r and t), when evaluated by the in vivo method were found to protect guinea-pigs from the histamine induced asphyxia and antagonized histamine in a competitive and reversible manner. With a pA2 value of 8.7 and protection time of 9.5 min (in vivo test), compound 10g was the most active amongst these five compounds. The isosteric replacement of the side chain -NH- in series 1, by oxygen and -NHSO2- functions, was undertaken to investigate the role of two amino functions in the receptor binding. This isosteric replacement with -O- does not affect the antihistaminic activity and the sedative potential of the series. Preliminary molecular modelling, studies indicate that the compounds with -NHSO2- in the side chain exhibit a closer fit with temelastine than their -O- isosteres. (C) 2000 Editions scientifiques et medicales Elsevier SAS.

Herbicidal compound

Herbicidal compounds are the compounds having the formula STR1 wherein R represents H or CH3 and X represents H or Cl.