13335-71-2

Basic information

• Product Name: 2,6-Dimethylphenoxyacetic acid
• Synonyms: AKOS BBB/198;AKOS BBS-00007717;(2,6-DIMETHYL-PHENOXY)-ACETIC ACID;ASINEX-REAG BAS 16434996;(2,6-Xylyloxy)-acetic Acid, (2,6-Dimethylphenoxy)acetic Acid, NSC 408599;(2,6-Dimethylphenoxy)acetic;acetic acid, (2,6-dimethylphenoxy)-;2-(2,6-dimethylphenoxy)ethanoic acid
• CAS NO: 13335-71-2
• Molecular Formula: C₁₀H₁₂O₃
• Molecular Weight: 180.2
• EINECS: 430-910-7
• Product Categories: Phenoxyacetic Acids and Alcohols (substituted);Aromatics Compounds;Aromatics
• Mol File: 13335-71-2.mol
• Article Data: 21

Chemical Properties

• Melting Point: 137-138°C
• Boiling Point: 299.1 °C at 760 mmHg
• Flash Point: 116.5 °C
• Appearance: white solid
• Density: 1.146 g/cm³
• Vapor Pressure: 0.000545mmHg at 25°C
• Storage Temp.: Refrigerator
• Solubility: Chloroform, Methanol
• PKA: pK1:3.356 (25°C)
• CAS DataBase Reference: 2,6-Dimethylphenoxyacetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-Dimethylphenoxyacetic acid(13335-71-2)
• EPA Substance Registry System: 2,6-Dimethylphenoxyacetic acid(13335-71-2)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 13335-71-2(Hazardous Substances Data)

Usage

Description

2,6-Dimethylphenoxyacetic acid, with the CAS number 13335-71-2, is a white solid compound that is useful in organic synthesis. It is characterized by the presence of a dimethylphenoxy group attached to an acetic acid moiety, which contributes to its unique chemical properties and potential applications.

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 
• 79-08-3 bromoacetic acid 
• 105-36-2 ethyl bromoacetate 
• 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

• 189357-33-3 KNI-727 
• 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 
• 898254-22-3 N-((2S,4S,5S)-5-(dibenzylamino)-4-hydroxy-1,6-diphenylhexan-2-yl)-2-(2,6-dimethylphenoxy)acetamide 
• 1190069-84-1 (R)-(4R)-N-((1S,2R)-2-hydroxy-1-indanyl)-3-(2-(2,6-dimethylphenoxyacetyl)amino-2-hydroxy-4-phenylbutanoyl)-5,5-dimethyl-1,3-thiazolidine-4-carboxamide 
• 1190069-82-9 (S)-(4R)-N-((1S,2R)-2-hydroxy-1-indanyl)-3-(2-phenethyl-3-(2-(2,6-dimethylphenoxy)acetamido)-2-hydroxypropanoyl)-5,5-dimethylthiazolidine-4-carboxamide 
• 1190069-96-5 (R)-(4S)-3-(2-benzyl-3-(2-(2,6-dimethylphenoxy)acetamido)-2-hydroxypropanoyl)-N-((1S,2R)-2-hydroxy-1-indanyl)-5,5-dimethylthiazolidine-4-carboxamide 
• 1190069-94-3 (S)-(4S)-3-(2-benzyl-3-(2-(2,6-dimethylphenoxy)acetamido)-2-hydroxypropanoyl)-N-((1S,2R)-2-hydroxy-1-indanyl)-5,5-dimethylthiazolidine-4-carboxamide 
• 1190069-92-1 (R)-(4S)-N-((1S,2R)-2-hydroxy-1-indanyl)-3-(2-phenethyl-3-(2-(2,6-dimethylphenoxy)acetamido)-2-hydroxypropanoyl)-5,5-dimethylthiazolidine-4-carboxamide 

Relevant articles and documents

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.

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.

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.).