701-99-5

Usage

Uses

Phenoxyacetyl chloride is used in the synthesis of:
1. Series of macrocyclic bis-β-lactams: These complex ring structures have potential applications in the development of new antibiotics and other medicinal compounds.
2. 5-phenyl-6-epiphenoxymethylpenicillin benzyl ester: Phenoxyacetyl chloride is a derivative of penicillin, a widely used antibiotic, and may have potential applications in medicine.
3. N-protected guanosine derivatives: These compounds are useful in RNA synthesis, which is an important area of research in molecular biology and drug development.
4. Phenyloxyketene: Phenoxyacetyl chloride is used for cycloaddition to imines, leading to the formation of β-lactams, which are a class of compounds with potential applications in medicine and as catalysts in organic synthesis.
In addition to these specific applications, Phenoxyacetyl chloride is also used in various chemical reactions to form esters, amides, and other functional groups, making it a valuable reagent in organic chemistry and pharmaceutical research.

Purification Methods

If it has no OH band in the IR then distil it in a vacuum, taking precautions for the moisture-sensitive compound. If it contains free acid (due to hydrolysis, OH bands in the IR), then add an equal volume of redistilled SOCl2, reflux for 2-3hours, evaporate and distil the residue in a vacuum as before. The amide has m 101o. [McElvain & Carney J Am Chem Soc 68 2592 1946, Beilstein 6 III 613.]

InChI:InChI=1/C8H7ClO2/c9-8(10)6-11-7-4-2-1-3-5-7/h1-5H,6H2

Upstream product

• 122-59-8 2-phenoxyacetic acid 
• 10026-13-8 phosphorus pentachloride 
• 108-95-2 phenol 
• 139-02-6 sodium phenoxide 
• 2555-49-9 phenoxyacetic acid ethyl ester 
• 79-11-8 chloroacetic acid 
• 2065-23-8 methyl 2-phenoxyacetate 
• 3598-16-1 2-phenoxyacetic acid sodium salt 

Downstream Products

• 7497-89-4 methyl 3-phenoxypropanoate 
• 66902-58-7 phenoxy-acetic acid-[3-(2-methyl-piperidino)-propylester]; hydrochloride 
• 102658-66-2 phenoxy-acetic acid-(1,1-dimethyl-3-piperidino-butyl ester); hydrochloride 
• 101939-11-1 3,3-dimethyl-4-phenoxyacetyl-piperazine-2,6-dione 
• 100623-20-9 2-chloromethyl-5-phenoxyacetoxy-pyran-4-one 
• 94576-80-4 phenoxy-acetic acid-(1-phenyl-2-pyrrolidino-ethyl ester); hydrochloride 
• 109725-68-0 phenoxy-acetic acid-[methyl-(2-oxo-indolin-3-ylidene)-hydrazide] 
• 101732-03-0 4-phenoxyacetyl-3-phenyl-piperazine-2,6-dione 
• 102955-54-4 phenoxy-acetic acid-(2,2-dimethyl-1-phenyl-3-piperidino-propylester); hydrochloride 
• 107855-45-8 phenoxyketene 
• 19054-87-6 1-(2,4-dimethyl-phenyl)-2-phenoxy-ethanone 
• 3743-69-9 N-(2-hydroxyphenyl)-2-phenoxyacetamide 
• 13920-29-1 6β-(methyl-phenoxyacetyl-amino)-penicillanic acid methyl ester 
• 58754-72-6 2-chloroacetyl-10-phenoxyacetyl-10H-phenothiazine 

Relevant academic research and scientific papers

Novel 4-(3-phenylpropionamido), 4-(2-phenoxyacetamido) and 4-(cinnamamido) substituted benzamides bearing the pyrazole or indazole nucleus: synthesis, biological evaluation and mechanism of action

Based on some common structural features of known compounds interfering with p53 pathways and our previously synthesized benzamides, we synthesized new ethyl 5-(4-substituted benzamido)-1-phenyl-1H-pyrazole-4-carboxylates 26a-c, ethyl 5-(4-substituted benzamido)-1-(pyridin-2-yl)-1H-pyrazole-4-carboxylates 27a-c and N-(1H-indazol-6-yl)-4-substituted benzamides 31a,b bearing in the 4 position of the benzamido moiety the 2-phenylpropanamido or 2-phenoxyacetamido or cinnamamido groups. A preliminary test to evaluate the antiproliferative activity against human lung carcinoma H292 cells highlighted how compound 26c showed the best activity. This last was therefore selected for further studies with the aim to find the mechanism of action. Compound 26c induces intrinsic apoptotic pathway by activating p53 and is also able to activate TRAIL-inducing death pathway by promoting increase of DR4 and DR5 death receptors, downregulation of c-FLIPL and caspase-8 activation.

Design, Synthesis, and Antifungal Evaluation of Cryptolepine Derivatives against Phytopathogenic Fungi

Inspired by the widely antiphytopathogenic application of diversified derivatives from natural sources, cryptolepine and its derivatives were subsequently designed, synthesized, and evaluated for their antifungal activities against four agriculturally important fungi Rhizoctonia solani, Botrytis cinerea, Fusarium graminearum, and Sclerotinia sclerotiorum. The results obtained from in vitro assay indicated that compounds a1-a24 showed great fungicidal property against B. cinerea (EC50 4 μg/mL); especially, a3 presented significantly prominent inhibitory activity with an EC50 of 0.027 μg/mL. In the pursuit of further expanding the antifungal spectrum of cryptolepine, ring-opened compound f1 produced better activity with an EC50 of 3.632 μg/mL against R. solani and an EC50 of 5.599 μg/mL against F. graminearum. Furthermore, a3 was selected to be a candidate to investigate its preliminary antifungal mechanism to B. cinerea, revealing that not only spore germination was effectively inhibited and the normal physiological structure of mycelium was severely undermined but also detrimental reactive oxygen was obviously accumulated and the normal function of the nucleus was fairly disordered. Besides, in vivo curative experiment against B. cinerea found that the therapeutic action of a3 was comparable to that of the positive control azoxystrobin. These results suggested that compound a3 could be regarded as a novel and promising agent against B. cinerea for its valuable potency.

Synthesis of N-trifluoromethyl amides from carboxylic acids

Found in biomolecules, pharmaceuticals, and agrochemicals, amide-containing molecules are ubiquitous in nature, and their derivatization represents a significant methodological goal in fluorine chemistry. Trifluoromethyl amides have emerged as important functional groups frequently found in pharmaceutical compounds. To date, there is no strategy for synthesizing N-trifluoromethyl amides from abundant organic carboxylic acid derivatives, which are ideal starting materials in amide synthesis. Here, we report the synthesis of N-trifluoromethyl amides from carboxylic acid halides and esters under mild conditions via isothiocyanates in the presence of silver fluoride at room temperature. Through this strategy, isothiocyanates are desulfurized with AgF, and then the formed derivative is acylated to afford N-trifluoromethyl amides, including previously inaccessible structures. This method shows broad scope, provides a platform for rapidly generating N-trifluoromethyl amides by virtue of the diversity and availability of both reaction partners, and should find application in the modification of advanced intermediates.

Design and synthesis of α-phenoxy-N-sulfonylphenyl acetamides as Trypanosoma brucei Leucyl-tRNA synthetase inhibitors

Human African trypanosomiasis (HAT), caused by the parasitic protozoa Trypanosoma brucei, is one of the fatal diseases in tropical areas and current medicines are insufficient. Thus, development of new drugs for HAT is urgently needed. Leucyl-tRNA synthetase (LeuRS), a recently clinically validated antimicrobial target, is an attractive target for development of antitrypanosomal drugs. In this work, we report a series of α-phenoxy-N-sulfonylphenyl acetamides as T. brucei LeuRS inhibitors. The most potent compound 28g showed an IC50 of 0.70 μM which was 250-fold more potent than the starting hit compound 1. The structure-activity relationship was also discussed. These acetamides provided a new scaffold and lead compounds for the further development of clinically useful antitrypanosomal agents.

Toward Soluble 5,10-Diheterotruxenes: Synthesis and Reactivity of 5,10-Dioxatruxenes, 5,10-Dithiatruxenes, and 5,10-Diazatruxenes

The following work presents three general approaches allowing, for the first time, the synthesis of 5,10-diheterotruxene derivatives containing two identical heteroatoms, namely, oxygen OOC, nitrogen NNC, or sulfur SSC. Two of described pathways involve the photocyclization of the corresponding triene 2 as a key step leading to a heptacyclic aromatic system. The third approach is based on the acidic condensation between ninhydrin 14 and benzo[b]heteroole 15. Typical functionalizations of the 5,10-diheterotruxene core have also been presented. In addition, the article discusses the advantages and limitations of the three suggested paths for receiving specific 5,10-diheterotruxene derivatives because the universal method suitable for obtaining molecules with any type of heteroatoms is not known so far.

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.

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.

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.

3 - (2 - Acetyl) -4 - hydroxy -6 - methyl pyran -2 - ketone derivatives and its application

The invention relates to a 3 - (2 - acetyl) - 4 - hydroxy - 6 - methyl-pyran - 2 - one derivatives and application. This kind of structure of the compound of the general formula (I), R, R1 Such as defined in the claims. In order to various phenol and chloroethyl acid methyl ester as the raw material, first of all by the substitution, hydrolysis, acylation reaction various phenoxy acetyl chloride, then with 4 - hydroxy - 6 - methyl-pyran - 2 - one condensation borate intermediate, finally through the Fries rearrangement reaction is obtained by the synthesis of 3 - (2 - acetyl) - 4 - hydroxy - 6 - methyl-pyran - 2 - one derivatives. The invention also relates to 3 - (2 - acetyl) - 4 - hydroxy - 6 - methyl-pyran - 2 - one derivatives in the herbicide application. Test results show that the compounds have good herbicidal activity, are a class of novel structure, application prospect of herbicide.

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.