13335-71-2

Usage

Uses

Used in Organic Synthesis:
2,6-Dimethylphenoxyacetic acid is used as a synthetic intermediate for the production of various organic compounds. Its unique structure allows it to be a versatile building block in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2,6-Dimethylphenoxyacetic acid is used as a key component in the development of new drugs. Its chemical properties make it suitable for the synthesis of active pharmaceutical ingredients (APIs) with potential therapeutic applications.
Used in Agrochemical Industry:
2,6-Dimethylphenoxyacetic acid is also utilized in the agrochemical industry for the synthesis of pesticides and other crop protection agents. Its unique structure can contribute to the development of novel and effective agrochemicals.
Used in Specialty Chemicals:
In the specialty chemicals sector, 2,6-Dimethylphenoxyacetic acid is employed as a raw material for the production of various specialty chemicals, such as dyes, fragrances, and other fine chemicals. Its versatility in organic synthesis makes it a valuable component in this industry.

InChI:InChI=1/C10H12O3/c1-7-4-3-5-8(2)10(7)13-6-9(11)12/h3-5H,6H2,1-2H3,(H,11,12)/p-1

Upstream product

• 576-26-1 2.6-dimethylphenol 
• 79-11-8 chloroacetic acid 
• 105-36-2 ethyl bromoacetate 
• 79-08-3 bromoacetic acid 
• 108-95-2 phenol 
• 6279-47-6 ethyl 2-(2,6-dimethylphenoxy)acetate 
• 38930-22-2 methyl 2-(2,6-dimethylphenoxy)acetate 
• 25117-01-5 2,6-dimethylphenolate anion 

Downstream Products

• 1148-08-9 2,6-Dimethyl-4-butyryl-phenoxyessigsaeure 
• 189357-33-3 KNI-727 
• 264884-01-7 N-{(1S,2R)-1-Benzyl-2-hydroxy-3-[isobutyl-(4-nitro-benzenesulfonyl)-amino]-propyl}-2-(2,6-dimethyl-phenoxy)-acetamide 
• 154612-58-5 (2S,4R)-1-{(2R,3S)-3-[2-(2,6-Dimethyl-phenoxy)-acetylamino]-2-hydroxy-4-phenyl-butyl}-4-(pyridin-4-ylsulfanyl)-piperidine-2-carboxylic acid tert-butylamide 
• 365442-03-1 KNI-840 
• 20143-48-0 2,6-dimethylphenoxyacetyl chloride 
• 1798014-18-2 (R)-N-{(1R,3R,4R)-1-Benzyl-4-[2-(2,6-dimethyl-phenoxy)-acetylamino]-3-hydroxy-5-phenyl-pentyl}-3-methyl-2-(2-oxo-tetrahydro-pyrimidin-1-yl)-butyramide 
• 192725-45-4 (2S,3S,5S)-2-(2,6-dimethylphenoxyacetyl)amino-3-hydroxy-5-(t-butyloxycarbonylamino)-1,6-diphenylhexane 
• 192725-98-7 (2S,3S,5S)-2-(2,6-dimethylphenoxyacetyl)amino-3-hydroxy-5-(t-butyloxycarbonylamino)-1-phenyl-6-methylheptane 
• 282539-54-2 (2S,3S,5S)-5-[N-tert-butyloxycarbonylamino]-2-[N-[2-(2,6-dimethylphenoxy)acetyl]amino]-3-hydroxy-7-methyl-1-phenyloctane 
• 497107-53-6 {(1S,3S,4S)-1-Butyl-4-[2-(2,6-dimethyl-phenoxy)-acetylamino]-3-hydroxy-5-phenyl-pentyl}-carbamic acid tert-butyl ester 
• 497107-54-7 [(1S,3S,4S)-4-[2-(2,6-Dimethyl-phenoxy)-acetylamino]-3-hydroxy-1-(3-methyl-butyl)-5-phenyl-pentyl]-carbamic acid tert-butyl ester 
• 497107-55-8 [(1S,3S,4S)-4-[2-(2,6-Dimethyl-phenoxy)-acetylamino]-1-(2-ethyl-butyl)-3-hydroxy-5-phenyl-pentyl]-carbamic acid tert-butyl ester 
• 521275-19-4 (2,6-dimethyl-phenoxy)-acetic acid N'-benzyl-hydrazide 

Relevant academic research and scientific papers

Production process of 2, 6-dimethylphenoxyacetic acid

The invention discloses a production process of 2, 6-dimethylphenoxyacetic acid, and belongs to the technical field of organic chemical industry. The upstream product 2, 6-dimethyl phenoxy acetic acidof 2, 6-dimethyl phenoxy acetyl chloride is prepared by controlling the two steps of substitution reaction and ester hydrolysis reaction, and the prepared 2, 6-dimethyl phenoxy acetic acid is high inpurity, does not generate large impurities, and is beneficial to subsequent preparation of lopinavir.

Synthesis and characterization of novel analogues of lopinavir

The present work describes the identification, origin, synthesis, characterization and control of four novel analogues of lopinavir viz. leucine analogue of lopinavir, isoleucine analogue of lopinavir, methyl analogue of lopinavir and dihydroxy analogue of lopinavir.

Formation of calix[4]arenes with acyloxycarboxylate functions

Calix[4]arenes are an exciting class of multifunctional compounds. Their ability to bind small molecules and ions actively makes them useful tools for many applications. While looking for a suitable chelating agent, a particular modification of the calix[4]arene led to an unexpected side reaction. In this work, we will describe the selective formation of the observed acyloxyacetate derivatives. The according yields can be regulated by controlling the water content of the solvent system. All new compounds were obtained in yields higher than 45percent and fully characterized by NMR, MS, EA, and X-ray crystallography. By performing and analyzing several reactions with different calix[4]arenes and monomeric derivatives, an explanation for the reaction mechanism was postulated. Further, we report on the modification of reaction conditions which were investigated to verify our findings’ veracity. In total, three acyloxyacetate derivatives were synthesized and characterized to support our conclusions.

Molecular tools that block maturation of the nuclear lamin A and decelerate cancer cell migration

Lamin A contributes to the structure of nuclei in all mammalian cells and plays an important role in cell division and migration. Mature lamin A is derived from a farnesylated precursor protein, known as prelamin A, which undergoes post-translational cleavage catalyzed by the zinc metalloprotease STE24 (ZPMSTE24). Accumulation of farnesylated prelamin A in the nuclear envelope compromises cell division, impairs mitosis and induces an increased expression of inflammatory gene products. ZMPSTE24 has been proposed as a potential therapeutic target in oncology. A library of peptidomimetic compounds were synthesized and screened for their ability to induce accumulation of prelamin A in cancer cells and block cell migration in pancreatic ductal adenocarcinoma cells. The results of this study suggest that inhibitors of lamin A maturation may interfere with cell migration, the biological process required for cancer metastasis.

Synthesis and anticonvulsant activity of phenoxyacetyl derivatives of amines, including aminoalkanols and amino acids

A series of 17 new phenoxyacetamides has been prepared via multistep chemical synthesis as a continuation of the research carried out by our group on di- and tri-substituted phenoxyalkyl and phenoxyacetyl derivatives of amines. The obtained compounds vary in an amide component, for example aminoalkanol or (un)modified amino acid moieties were introduced. The structures of selected products were confirmed by means of crystallographic methods. All 17 compounds were the subject of preliminary screening for potential anticonvulsant activity (MES, 6 Hz and/or scMET tests) and neurotoxicity (rotarod) in mice after intraperitoneal administration, while several active compounds were subsequently examined in additional models (e.g. MES and rotarod-rats, p.o. or i.p., hippocampal kindling-rats, i.p.). Finally, safety studies (cytotoxicity and cell proliferation assays on astrocytes, metabolic stability assessment, mutagenicity evaluation) were performed for several active compounds, including the most promising one (R-(?)-2-(2,6-dimethylphenoxy)-N-(1-hydroxypropan-2-yl)acetamide, MES ED50 = 12.00 mg per kg b.w., rats, p.o.).

2,6-dimethyl phenoxyacetic acid synthesis and purification method

The invention relates to the field of pharmaceutical intermediates, in particular to a 2,6-dimethyl phenoxyacetic acid synthesis and purification method. The method includes: dropwise adding a sodium hydroxide solution for the first time after dropwise adding haloacetic acid into a water solution of 2,6-dimethylphenol for the first time, and controlling the temperature below 35 DEG C in a sodium hydroxide solution adding process; heating after dropwise adding is finished, and refluxing for 1-4h; dropwise adding the sodium hydroxide solution for the second time after adding haloacetic acid for the second time; after dropwise adding is finished, refluxing for 6-8h until reaction is completed. According to the 2,6-dimethyl phenoxyacetic acid synthesis and purification method, haloacetic acid and sodium hydroxide are dropwise added separately and respectively added in two times; reaction procedures are monitored according to pH values, and when PH of reaction liquid is larger than or equal to 13 or smaller than or equal to 7 in a reaction process, raw materials are timely replenished after reaction is stopped, so that reaction time is shortened. By the 2,6-dimethyl phenoxyacetic acid synthesis and purification method, consumption of the haloacetic acid is greatly reduced, and reaction time is not longer than 24 hours.

DERIVATIVES OF AMINOALKANOLS, METHOD OF OBTAINING OF AMINOALKANOLS AND THEIR USE

The subject of the invention is a group of new derivatives of aminoalkaπols, more specifically [(phenoxy)alkyl]aminoalkanols and [(phenoxy)acyl)aminoalkanols, their method of obtaining and their use for production of a medicine which is used in the prophylaxis, prevention and/or treatment of diseases or symptoms having neurological background and for production of a medicine with anticonvulsant activity, which is used in seizures of various origin, also in the limbic system, in myoclonic or sound-induced seizures, in psychomotor epilepsy, as well as in relieving neuropathic or inflammatory pain.

Preliminary evaluation of anticonvulsant activity and neurotoxicity of some 1,4-substituted piperazine derivatives

A series of 1,4-piperazine derivatives was synthesized and evaluated for anticonvulsant activity in the maximal electroshock seizure (MES) and subcutaneous pentylenetetrazole seizure threshold (ScMet) assays and for neurotoxicity (TOX). The compounds were only moderately effective. The anticonvulsant activity was accompanied by neurotoxicity. 1-[(4-Chlor-3- methylphenoxy)-acetyl]-4-(2-methoxyphenyl)-piperazine was also evaluated in six hertz seizure test (6-Hz) and showed good activity. At the dose of 100 mg/kg b. w. the compound produced 100% protection after 0.5 h without neurotoxic effect.

Anti-coronavirus compounds

A method of treating coronavirus infection. The method includes administering to a subject suffering from or being at risk of suffering from such infection an effective amount of a compound of formula (I). Each variable in this formula is defined in the specification.

A novel dipeptide-based HIV protease inhibitor containing allophenylnorstatine

Dipeptide analogues incorporating allophenylnorstatine [Apns; (2S,3S)-3-amino-2-hydroxy-4-phenylbutyric acid] as a transition state mimic at the scissile bond were designed and synthesized in the hope of obtaining a novel KNI series of HIV protease inhibitors. The precursors, N-P2′- 3-(2S,3S)-3-(tert-butyloxycarbonyl)amino-2-hydroxy-4-phenylbutanoyl)-5, 5-dimethylthiazolidine-4-carboxamide (N-Boc-Apns-Dmt-P2′) 4a-p were prepared by deprotection of the synthones N-P2′-(tert- butyloxycarbonyl)-5,5-dimethylthiazolidine-4-carboxamide (Boc-Dmt-P 2′) 2a-p, then coupling with (2S,3S)3-(tert-butyloxycarbonyl) amino-2-hydroxy-4-phenylbutanoic acid (N-Boc-Apns-OH) 3. The deprotected intermediates 4 were coupled with the activated carboxyl groups of the P 2 ligands to afford the target dipeptides. In this work, we fixed at the P2 site either a 2,6-dimethylphenoxyacetyl or a 3-hydroxy-2-methylbenzoyl group. Substitutes at the P2′ site were varied to afford the members of the series 7 and 8. Improved activity of most of the members of series 8 relative to their analogues of series 7 can be partially attributed to the differences in the structures of the P2 moieties. Positional isomerism in the P2′ moieties significantly affected the activity and polarity of the target.