4122-68-3

Usage

Uses

Used in Pharmaceutical Industry:
4-Chlorophenoxyacetyl chloride is used as a synthetic intermediate for the preparation of various pharmaceutical compounds. Its application is primarily due to its reactivity and ability to form new chemical entities with potential therapeutic properties.
Used in Chemical Synthesis:
In the field of chemical synthesis, 4-chlorophenoxyacetyl chloride is used as a key building block for the creation of substituted acetophenone derivatives. These derivatives have a wide range of applications, including their use as intermediates in the synthesis of various organic compounds.
Used in Organic Chemistry Research:
4-Chlorophenoxyacetyl chloride is also utilized in organic chemistry research for the synthesis of complex molecules, such as 2-(4-chlorophenoxyacetylamino)-3-ethoxycarbonyl[2,3-b]quinuclidine and 2-(4-chlorophenoxy)-N′-[2-(4-chlorophenoxy)acetyl]acetohydrazide monohydrate. These compounds are of interest due to their potential applications in various fields, including pharmaceuticals and materials science.
Overall, 4-chlorophenoxyacetyl chloride is a versatile compound with applications in the pharmaceutical industry, chemical synthesis, and organic chemistry research. Its uses are driven by its reactivity and ability to form new chemical entities with potential applications in various fields.

InChI:InChI=1/C8H6Cl2O2/c9-6-1-3-7(4-2-6)12-5-8(10)11/h1-4H,5H2

Upstream product

• 122-88-3 4-Chlorophenoxyacetic acid 
• 4841-22-9 (4-chloro-phenoxy)-acetic acid methyl ester 
• 106-48-9 4-chloro-phenol 
• 79-11-8 chloroacetic acid 
• 14426-42-7 ethyl p-chlorophenoxyacetate 
• 36304-28-6 tert-butyl 2-(4-chlorophenoxy)acetate 
• 1193-00-6 sodium 4-chlorophenolate 

Downstream Products

• 403-98-5 (4-chloro-phenoxy)-acetic acid-(3-trifluoromethyl-anilide) 
• 54393-15-6 4-[2-(4-chloro-phenoxy)-acetylamino]-benzoic acid 
• 7462-17-1 2-(4-chlorophenoxy)-N-(2-hydroxyethyl)acetamide 
• 62095-40-3 (4-chloro-phenoxy)-acetic acid-(4-chloro-phenyl ester) 
• 130831-41-3 N-[(4-chloro-phenoxy)-acetyl]-N-phenyl-glycine 
• 221148-11-4 (4-chloro-phenoxy)-ketene 
• 3685-84-5 meclofenoxate hydrochloride 
• 106852-27-1 (S)-2-(2-(4-chlorophenoxy)acetamido)propanoic acid 
• 106852-27-1 N-[(4-chloro-phenoxy)-acetyl]-D-alanine 
• 106852-27-1 N-[(4-chloro-phenoxy)-acetyl]-DL-alanine 
• 31413-00-0 N-[(4-chloro-phenoxy)-acetyl]-valine 
• 106852-19-1 N-[(4-chloro-phenoxy)-acetyl]-D_s-threonine 
• 106852-19-1 N-[(4-chloro-phenoxy)-acetyl]-L_s-threonine 
• 106852-19-1 N-[(4-chloro-phenoxy)-acetyl]-DL-threonine 

Relevant academic research and scientific papers

A Convenient One-Pot Synthesis of 1,5-Disubstituted Tetrazoles Containing an Amino or a Carboxy Group

Abstract: A convenient method is proposed for constructing the tetrazole ring by a one-pot reaction of amides with phosphorus oxychloride and sodium azide. A series of 1,5-disubstituted tetrazoles containing an amino or a carboxy group, which present interest as buildings blocks for the synthesis of biologically active substances, were obtained.

A meclofenoxate hydrochloride preparation method

The invention discloses a meclofenoxate hydrochloride of the preparation method, comprises the following steps: (A) will acid with thionyl chloride in chlorobenzene acyl chloride reaction, to obtain the chlorophenoxy acetyl chloride; (B) step (A) to get chlorophenoxy acetyl chloride and dimethyl amino ethanol by condensation reaction to obtain the meclofenoxate free alkali; (C) step (B) to obtain the free base of the salt-forming acid salt, thermal insulation and filtering to obtain the hydrochloride. The invention easy availability of raw materials, the reaction temperature is low, the operation is convenient, the crude product of high purity, stable quality, the present invention provides a more easy operation, more environmentally friendly, more economic meclofenoxate hydrochloride synthetic pathway.

Design and Synthesis of Novel 4-Hydroxyl-3-(2-phenoxyacetyl)-pyran-2-one Derivatives for Use as Herbicides and Evaluation of Their Mode of Action

In order to develop a novel herbicide containing the β-triketone motif, a series of 4-hydroxyl-3-(2-phenoxyacetyl)-pyran-2-one derivatives were designed and synthesized. The bioassay results showed that compound II15 had good pre-emergent herbicidal activity even at a dosage of 187.5 g ha-1. Moreover, compound II15 showed a broader spectrum of weed control when compared with a commercial herbicide 2,4-dichlorophenoxyacetic acid (2,4-D), and displayed good crop safety to Triticum aestivum L. and Zea mays Linn. when applied at 375 g ha-1 under pre-emergence conditions, which indicated its great potential as a herbicide. More importantly, studying the molecular mode of action of compound II15 revealed that the novel triketone structure is a proherbicide of its corresponding phenoxyacetic acid auxin herbicide, which has a herbicidal mechanism similar to that of 2,4-D. The present work indicates that the 4-hydroxyl-3-(2-phenoxyacetyl)-pyran-2-one motif may be a potential lead structure for further development of novel auxin-type herbicides.

Structure-based design, synthesis and evaluation of 2,4-diaminopyrimidine derivatives as novel caspase-1 inhibitors

Interleukin-1β converting enzyme contributes in various inflammatory and autoimmune diseases by maturing pro-inflammatory cytokines IL-1β, IL-18 and IL-33. Therefore, inhibition caspase-1 may provide a potential therapeutic strategy for the treatment of chronic inflammatory diseases. Here we have reported structure-based design, synthesis and biological evaluation of 2,4-diaminopyrimidine derivatives (6a-6w) as potential caspase-1 inhibitors. Six compounds 6m, 6n, 6o, 6p, 6q and 6r showed significant enzymatic inhibition with IC5 0 ranging from 0.022 to 0.078 μM. These compounds also displayed excellent cellular potency at sub-micromolar concentration. Moreover, molecular docking studies provided the useful binding insights specific for caspase-1 inhibition. All these results indicated that compounds 6m, 6n and 6o could be potential leads for the development of newer caspase-1 inhibitors as anti-inflammatory agents.

Esterquat herbicidal ionic liquids (HILs) with two different herbicides: Evaluation of activity and phytotoxicity

Herbicidal ionic liquids (HILs) constitute a new concept in crop protection products. Their main advantage is the potential to combine the efficiency of traditional herbicides with low vapour pressure and adjustable water solubility which leads to improved environmental safety in the agricultural sector. Among many strategies to obtain new HILs, esterquats seem to be well suited for modification since both the cation and anion may be constituents of herbicides. In the framework of this study 16 new esterquat HILs were synthetized based on standard herbicides: 2,4-D, MCPA, MCPP, 4-CPA, Clopyralid and Dicamba. Germination tests performed on agricultural soil using cornflower indicated the best two HILs. Furthermore, analysis of the toxicological effects of HILs on wheat plants revealed an additional advantage of the two selected HILs. The glutathione (GSH) content and glutathione S-transferase (GST) activity showed a lower oxidative stress level in wheat plants treated with examined HILs, respectively, in comparison to a mixture of reference compounds. Finally the Ames test was applied in order to analyse the mutagenic activity of the two selected HILs.

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 Antimicrobial Activity of Novel 2-Substituted Phenoxy-N-(4-substituted Phenyl-5-(1H-1,2,4-triazol-1-yl)thiazol-2-yl)acetamide Derivatives

A series of 2-substituted phenoxy-N-(4-substituted phenyl-5-(1H-1,2,4-triazol-1-yl)thiazole-2-yl)acetamide derivatives 8a, 8b, 8c, 8d, 8e, 8f, 8g, 8h, 8i, 8j, 8k, 8l, 8m, 8n, 8o, 8p, 8q, 8r, 8s, 8t was synthesized by the reaction of phenoxyacetyl chloride 7 with intermediate 4-substituted phenyl-5-(1H-1,2,4-triazol-1-yl)thiazol-2-amine 5. Their structures were confirmed by 1H NMR, 13C NMR, MS, IR, and elemental analyses. The synthesized compounds were also screened for their antimicrobial activity against three types of plant fungi (Gibberella zeae, Phytophthora infestans, and Paralepetopsis sasakii) and two kinds of bacteria [Xanthomonas oryzae pv. oryzae (Xoo) and Xanthomonas axonopodis pv. citri (Xac)] showing promising results. In particular, 8b, 8f, 8g, and 8h exhibited excellent antibacterial activity against Xoo, with 50% effective concentration (EC50) values of 35.2, 80.1, 62.5, and 82.1 μg/mL, respectively, which are superior to the commercial antibacterial agent bismerthiazol (89.9 μg/mL). The preliminary structure–activity relationship studies of these compounds are also briefly described.

Discovery and development of a novel class of phenoxyacetyl amides as highly potent TRPM8 agonists for use as cooling agents

The paper presents the activity trends for a novel series of phenoxyacetyl amides as human TRPM8 receptor agonists. This series encompasses in vitro activity values ranging from the micromolar to the picomolar levels. Sensory evaluation of these molecules highlights their relevance as cooling agents for oral applications. The positive outcome of the complete evaluation of N-(1H-pyrazol-3-yl)-N-(thiophen-2-ylmethyl)-2-(p-tolyloxy)acetamide resulted in its approval for Generally Recognized As Safe (GRAS) status by the Flavor & Extract Manufacturer Association (FEMA) as FEMA 4809.

Synthesis of novel 1,2,5-oxadiazoles and evaluation of action against Acinetobacter baumannii

With multidrug resistant bacteria on the rise, novel antibiotics are becoming highly sought after. In 2008, eleven compounds were identified by high throughput screening as inhibitors of BasE, a key enzyme of the non-ribosomal peptide synthetase pathway found in Acinetobacter baumannii. Herein, we describe the preparation of four structurally similar heterocyclic lead compounds from that study, including one 1,2,5-oxadiazole. A further library of 30 analogues containing the oxadiazole moiety was then generated. All compounds were screened against Acinetobacter baumannii and their minimum inhibitory concentration data is reported, with (E)-3-(2-hydroxyphenyl)-N-(4-methyl-1,2,5-oxadiazol-3-yl)acrylamide 32 found to have an MIC of 0.5 mM. This work provides the foundation for further investigation of 1,2,5-oxadizoles as novel inhibitors of A. baumannii.

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.