1878-87-1

Usage

Uses

Used in Pharmaceutical Industry:
2-Nitrophenoxyacetic acid is used as an intermediate compound for the synthesis of various pharmaceutical products. Its unique structure allows it to be a key component in the development of new drugs, potentially contributing to the treatment of various medical conditions.
Used in Chemical Research:
In the field of chemical research, 2-Nitrophenoxyacetic acid serves as a valuable compound for studying the properties and reactions of substituted acetic acids. Its distinct chemical structure makes it an interesting subject for exploring new reaction pathways and understanding the behavior of related compounds.
Used in Material Science:
2-Nitrophenoxyacetic acid can be utilized in the development of novel materials with specific properties, such as improved stability or reactivity. Its unique structure may contribute to the creation of advanced materials for various applications, including coatings, adhesives, or polymers.
Used in Analytical Chemistry:
As a compound with distinct chemical properties, 2-Nitrophenoxyacetic acid can be employed in analytical chemistry for the development of new methods or techniques for the detection, identification, or quantification of related compounds. This can be particularly useful in environmental monitoring, quality control, or forensic analysis.

Purification Methods

Crystallise the acid from water, and dry it over P2O5 in vacuo. The S-benzylisothiuronium salt has m 155-156o (from EtOH). [Hayes & Brooch J Am Chem Soc 65 1577 1943, Beilstein 6 H 220, 6 II 211, 6 III 804, 6 IV 1261.]

InChI:InChI=1/C8H7NO5/c10-8(11)5-14-7-4-2-1-3-6(7)9(12)13/h1-4H,5H2,(H,10,11)/p-1

Upstream product

• 37682-31-8 ethyl o-nitrophenoxyacetate 
• 3926-62-3 sodium monochloroacetic acid 
• 824-39-5 sodium o-nitrophenate 
• 105-36-2 ethyl bromoacetate 
• 79-11-8 chloroacetic acid 
• 88-75-5 2-hydroxynitrobenzene 
• 122-59-8 2-phenoxyacetic acid 
• 7506-93-6 2-(2-nitrophenoxy)-acetic acid methyl ester 
• 207444-89-1 (2-nitrophenoxy)-acetic acid tert-butyl ester 

Downstream Products

• 37682-31-8 ethyl o-nitrophenoxyacetate 
• 105106-02-3 (2-nitro-phenoxy)-acetic acid-(3-chloro-but-2ξ-enyl ester) 
• 5466-88-6 3,4-dihydro-3-oxo-2H-1,4-benzoxazine 
• 27320-99-6 3,4-dihydro-7-chloro-3-oxo-2H-1,4-benzoxazine 
• 20142-87-4 2-(2-nitrophenoxy)acetyl chloride 
• 4323-68-6 2-aminophenoxyacetic acid 
• 97788-41-5 (2,2'-azo-diphenoxy)-di-acetic acid 
• 64381-28-8 (2-Nitro-phenoxy)-acetic acid (2,6-dichloro-phenoxycarbonylamino)-methyl ester 
• 64381-33-5 (2-Nitro-phenoxy)-acetic acid (3,5-dimethyl-4-methylsulfanyl-phenoxycarbonylamino)-methyl ester 
• 771-26-6 4-hydroxy-2H-1,4-benzoxazin-3-one 
• 7506-93-6 2-(2-nitrophenoxy)-acetic acid methyl ester 
• 86926-84-3 sodium o-aminophenoxyacetate 
• 5513-43-9 (4-Chlormethyl-2-nitrophenoxy)-essigsaeure 
• 6170-67-8 2-(o-Chlorbenzamid)phenoxyessigsaeure 

Relevant academic research and scientific papers

Quantitative helix handedness bias through a single Hvs.CH3stereochemical differentiation

A novel chiral aromatic δ-amino acid building block was shown to fully induce handedness in quinoline oligoamide foldamers with the possibility of further increasing the bias by combining multiples of these units in the same sequence. Through its incorporation within the helix, both N- and C-termini are still accessible for further functionalisation.

Design, synthesis and biological evaluation of oxime lacking Psammaplin inspired chemical libraries as anti-cancer agents

In this study, we attempted the chemical simplification of Psammaplin (PsA), while retaining its activity in vitro. Inspired by the previous Structure Activity Relationship (SAR) studies on various PsA analogues and relying on the fact that oxime is metabolically unstable, we initially designed and synthesized a diverse library of PsA analogues and evaluated for cytotoxic activity. Among 32 compounds of Psammaplin analogues synthesized, the compound 10b was almost equally active as parent Psammaplin in vitro.

Synthesis and herbicidal activities of aryloxyacetic acid derivatives as HPPD inhibitors

A series of aryloxyacetic acid derivatives were designed and synthesized as 4-hydoxyphenylpyruvate dioxygenase (HPPD) inhibitors. Preliminary bioassay results reveal that these derivatives are promising Arabidopsis thaliana HPPD (AtHPPD) inhibitors, in particular compounds I12 (Ki = 0.011 μM) and I23 (Ki = 0.012 μM), which exhibit similar activities to that of mesotrione, a commercial HPPD herbicide (Ki = 0.013 μM). Furthermore, the newly synthesized compounds show significant greenhouse herbicidal activities against tested weeds at dosages of 150 g ai/ha. In particular, II4 exhibited high herbicidal activity for pre-emergence treatment that was slightly better than that of mesotrione. In addition, compound II4 was safe for weed control in maize fields at a rate of 150 g ai/ha, and was identified as the most potent candidate for a novel HPPD inhibitor herbicide. The compounds described herein may provide useful guidance for the design of new HPPD inhibiting herbicides and their modification.

An Efficient One-Pot Synthesis of 2-(Aryloxyacetyl)cyclohexane-1,3-diones as Herbicidal 4-Hydroxyphenylpyruvate Dioxygenase Inhibitors

4-Hydroxyphenylpyruvate dioxygenase (EC 1.13.11.27, HPPD) is an important target for new bleaching herbicides discovery. As a continuous work to discover novel crop selective HPPD inhibitor, a series of 2-(aryloxyacetyl)cyclohexane-1,3-diones were rationally designed and synthesized by an efficient one-pot procedure using N,N′-carbonyldiimidazole (CDI), triethylamine, and acetone cyanohydrin in CH2Cl2. A total of 58 triketone compounds were synthesized in good to excellent yields. Some of the triketones displayed potent in vitro Arabidopsis thaliana HPPD (AtHPPD) inhibitory activity. 2-(2-((1-Bromonaphthalen-2-yl)oxy)acetyl)-3-hydroxycyclohex-2-en-1-one, II-13, displayed high, broad-spectrum, and postemergent herbicidal activity at the dosage of 37.5-150 g ai/ha, nearly as potent as mesotrione against some weeds. Furthermore, II-13 showed good crop safety against maize and canola at the rate of 150 g ai/ha, indicating that II-13 might have potential as a herbicide for weed control in maize and canola fields. II-13 is the first HPPD inhibitor showing good crop safety toward canola.

Finding new elicitors that induce resistance in rice to the white-backed planthopper Sogatella furcifera

Herein we report a new way to identify chemical elicitors that induce resistance in rice to herbivores. Using this method, by quantifying the induction of chemicals for GUS activity in a specific screening system that we established previously, 5 candidate elicitors were selected from the 29 designed and synthesized phenoxyalkanoic acid derivatives. Bioassays confirmed that these candidate elicitors could induce plant defense and then repel feeding of white-backed planthopper Sogatella furcifera.

Identification of the novel N-phenylbenzenesulfonamide derivatives as potent HIV inhibitors

Searching for more safe and effective agents for HIV treatments is still an urgent topic worldwide. Based on our continuous modifications on the benzophenone derivatives as HIV-1 reverse transcriptase (RT) inhibitors, a new template bearing N-phenylbenzenesulfonamide (PBSA) structure was designed to enhance the interactions with HIV-1 RT. In this manuscript, a series of PBSA derivatives were synthesized and evaluated for their anti-HIV-1 activity. The preliminary test showed that these compounds were potent to inhibit wild-type HIV-1 with EC50 values ranging of 0.105-14.531 μmol/L. In particular, compound 13f not only has high anti-HIV-1 activity (0.108 μmol/L), but also possesses low toxicity with a TI value of 1816.6. Furthermore, the major interactions of the inhibitor 13f with HIV-1 RT were also investigated using the molecular modelling. Our discovered structure-activity relationships (SARs) of these analogues may serve as an important clue for further optimizations.

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.

Aza-Michael addition of acrylonitrile with 2-aryloxymethylbenzimidazole derivatives under microwave irradiation

A simple, rapid, and highly efficient method has been developed for the aza-Michael addition of acrylonitrile to 2-aryl-oxymethylbenzimidazole derivatives in the presence of anhydrous potassium carbonate under microwave irradiation. A series novel of 1-cyanoethyl-2-aryloxymethylbenzimidazole derivatives have been prepared and characterised by 1H NMR, 13C NMR, IR spectra and elemental analysis.

Synthesis and anti-inflammatory activity of 2-aryloxy methyl oxazolines

A series of potential biologically active 2-aryloxy methyl oxazolines 3a-n have been synthesized from substituted hydroxybenzenes 1a-n with good chemical yield. The compounds 3a-n were screened for their anti-inflammatory, ulcerogenic, cyclooxygenase activities and also for their acute toxicity. The potency of the compounds was compared with that of the standard drugs, aspirin and phenyl butazone. The outcome indicates that compounds 3b (48.2%), 3h (48.5%) and 3l (46.5%) offered significant anti-inflammatory activity with low ulcerogenic activity than the standard drugs.

Induced helix of 2-(2-aminophenoxy)alkanoic acid oligomers as a δ-peptidomimetic foldamer

Peptidomimetic foldamers were synthesized by oligomerizing derivatives of the δ-amino acid analogue, 2-(2-aminophenoxy)alkanoic acid. Single-crystal analysis of the tetramer reveals a 21-helical secondary structure stabilized by hydrogen bonding and the coiled stacking of aromatic rings. The M-helicity of 2-aminophenoxyacetic acid oligomers was induced by the incorporation of only a single chiral carbon of the N-terminal (R)-2-(2-nitrophenoxy)propionamide moiety. The solution state CD spectra demonstrated that the resulting helix induced a substantial Cotton effect. The secondary structure was further characterized by IR and NMR spectroscopy.