14920-81-1

Basic information

• Product Name: Methyl 2,6-dimethylbenzoate
• Synonyms: 2,6-Dimethylbenzoic acid methyl ester;Methyl 2,6-dimethylbenzoate
• CAS NO: 14920-81-1
• Molecular Formula: C₁₀H₁₂O₂
• Molecular Weight: 164.20
• Mol File: 14920-81-1.mol

Chemical Properties

• Boiling Point: 215.7 °C at 760 mmHg
• Flash Point: 87.3 °C
• Appearance: /
• Density: 1.027 g/cm³
• Vapor Pressure: 0.146mmHg at 25°C
• Refractive Index: 1.508
• Storage Temp.: Room temperature.
• CAS DataBase Reference: Methyl 2,6-dimethylbenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 2,6-dimethylbenzoate(14920-81-1)
• EPA Substance Registry System: Methyl 2,6-dimethylbenzoate(14920-81-1)

Safety Data

• Hazardous Substances Data: 14920-81-1(Hazardous Substances Data)

Usage

Uses

Used in Fragrance Industry:
Methyl 2,6-dimethylbenzoate is used as a fragrance ingredient for its floral scent, adding a pleasant aroma to perfumes and personal care products.
Used in Food and Beverage Industry:
It serves as a flavoring agent, enhancing the taste profiles of various food and beverages, contributing to their overall sensory appeal.
Used in Pharmaceutical Industry:
Methyl 2,6-dimethylbenzoate is utilized in the production of pharmaceuticals, potentially due to its ability to serve as a solvent or intermediate in the synthesis of medicinal compounds.
Used in Agrochemical Industry:
Methyl 2,6-dimethylbenzoate finds application in the agrochemical sector, possibly for its role in the formulation of pesticides or other agricultural products.
Used in Organic Synthesis:
Methyl 2,6-dimethylbenzoate is employed as a solvent in organic synthesis, facilitating various chemical reactions due to its solubility properties.
Used in Insect Repellent Industry:
It is also a component in insect repellents, likely due to its ability to deter insects, providing a practical application in pest control and personal protection products.

InChI:InChI=1/C10H12O2/c1-7-5-4-6-8(2)9(7)10(11)12-3/h4-6H,1-3H3

Upstream product

• 186581-53-3 diazomethane 
• 632-46-2 2,6-dimethylbenzoic acid 
• 67-56-1 methanol 
• 77-78-1 dimethyl sulfate 
• 21900-37-8 2,6-dimethylbenzoyl chloride 
• 41264-06-6 methyl 4,6-dimethyl-2-oxo-2H-pyran-5-carboxylate 
• 109-92-2 ethyl vinyl ether 
• 598-99-2 Methyl trichloroacetate 
• 107941-45-7 methyl 1,5-dimethyl-8-ethoxy-3-oxo-2-oxabicyclo<2.2.2>-oct-5-ene-6-carboxylate 
• 74-88-4 methyl iodide 
• 86364-02-5 2,6-dimethylphenyl trifluoromethanesulphonate 
• 70588-24-8 methyl 1-methyl-6-oxo-cyclohexa-2,4-diene-1-carboxylate 
• 87-62-7 2,6-dimethylaniline 
• 576-26-1 2.6-dimethylphenol 

Downstream Products

• 2142-76-9 2',6'-dimethylacetophenone 
• 56263-51-5 methyl 2,6-di(bromomethyl)benzoate 
• 62285-58-9 2,6-dimethylbenzyl alcohol 
• 108734-57-2 2-Benzenesulfonylmethyl-6-methyl-benzoic acid methyl ester 
• 766-92-7 [(methylthio)methyl]-benzene 
• 69795-09-1 sodium 2,6-dimethylbenzoate 
• 56427-77-1 2-bromomethyl-6-methyl-benzoic acid methyl ester 
• 70759-62-5 methyl 2,6-dimethyl-3,5-bis(chloromethyl)benzoate 
• 2211-84-9 7-methyl-3H-isobenzofuran-1-one 
• 632-46-2 2,6-dimethylbenzoic acid 
• 927887-32-9 2,6-dimethylbenzyl alcohol-1,1-d2 
• 186538-17-0 (R)-N-(2,6-dimethylbenzyl)-1,3-thiazolidine-4-carboxamide 
• 1027226-32-9 4-(2,6-dimethyl-benzylcarbamoyl)-thiazolidine-3-carboxylic acid tert-butyl ester 
• 226997-95-1 (R)-N-(2,6-dimethylbenzyl)-3-<(2S,3S)-3-amino-2-hydroxy-4-phenylbutanoyl>-1,3-thiazolidine-4-carboxamide 

Relevant articles and documents

Methyl group transfer upon gas phase decomposition of protonated methyl benzoate and similar compounds

Gas phase decompositions of protonated methyl benzoate and its conjugates have been studied by using electrospray ionization-collision induced dissociation-tandem mass spectrometry. Loss of CO2 molecule, thus transfer of methyl group, has been observed. In order to better understand this process, the theoretical calculations have been performed. For methyl benzoate conjugates, it has been found that position of substituent affects the loss of CO2 molecule, not the electron donor/withdrawing properties of the substituent. Therefore, electrospray ionization-mass spectrometry in positive ion mode may be useful for differentiation of isomers of methyl benzoate conjugates.

Intramolecular rearrangements of but-3-enoic esters

Support for the proposal by Khalafy and Prager1 of a cheletropic rearrangement of a 6-methylidenecyclohexa-2,4-diene-1-carboxylate under flash vacuum pyrolysis (f.v.p.) conditions has been obtained by a study of the f.v.p. products obtained from methyl 1-methyl-6-methylidenecyclohexa-2,4-diene-1-carboxylate and methyl 2,2-dimethylbut-3-enoate. A significant product in each case arises from a reaction involving decarbonylation and transfer of a methoxy group to C4 (but-3-enoate numbering). CSIRO 2000.

GPR52 Antagonist Reduces Huntingtin Levels and Ameliorates Huntington's Disease-Related Phenotypes

GPR52 is an orphan G protein-coupled receptor (GPCR) that has been recently implicated as a potential drug target of Huntington's disease (HD), an incurable monogenic neurodegenerative disorder. In this research, we found that striatal knockdown of GPR52 reduces mHTT levels in adult HdhQ140 mice, validating GPR52 as an HD target. In addition, we discovered a highly potent and specific GPR52 antagonist Comp-43 with an IC50 value of 0.63 μM by a structure-activity relationship (SAR) study. Further studies showed that Comp-43 reduces mHTT levels by targeting GPR52 and promotes survival of mouse primary striatal neurons. Moreover, in vivo study showed that Comp-43 not only reduces mHTT levels but also rescues HD-related phenotypes in HdhQ140 mice. Taken together, our study confirms that inhibition of GPR52 is a promising strategy for HD therapy, and the GPR52 antagonist Comp-43 might serve as a lead compound for further investigation.

Milled Dry Ice as a C1 Source for the Carboxylation of Aryl Halides

The use of carbon dioxide as a C1 chemical feedstock remains an active field of research. Here we showcase the use of milled dry ice as a method to promote the availability of CO 2in a reaction solution, permitting practical synthesis of arylcarboxylic acids. Notably, the use of milled dry ice produces marked increases in yields relative to those obtained with gaseous CO 2, as previously reported in the literature.

Robust synthesis of NIR-emissive P-rhodamine fluorophores

P-Rhodamines were accessed by implementing a robust three step sequence consisting of (i) addition of m-metallated anilines to dichlorophosphine oxides, (ii) selective dibromination, and (iii) cyclization of the diaryllithium reagents derived from the dib

Synthesis and Characterization of Acridinium Dyes for Photoredox Catalysis

Photoredox catalysis is a rapidly evolving platform for synthetic methods development. The prominent use of acridinium salts as a sustainable option for photoredox catalysts has driven the development of more robust and synthetically useful versions based on this scaffold. However, more complicated syntheses, increased cost, and limited commercial availability have hindered the adoption of these catalysts by the greater synthetic community. By utilizing the direct conversion of a xanthylium salt into the corresponding acridinium as the key transformation, we present an efficient and scalable preparation of the most synthetically useful acridinium reported to date. This divergent strategy also enabled the preparation of a suite of novel acridinium dyes, allowing for a systematic investigation of substitution effects on their photophysical properties.

APELIN RECEPTOR AGONISTS AND METHODS OF USE THEREOF

Provided herein are agonists of the apelin receptor for the treatment of disease. The compounds disclosed herein are useful for the treatment of a range of cardiovascular, renal and metabolic conditions.

Streamlined Total Synthesis of Uncialamycin and Its Application to the Synthesis of Designed Analogues for Biological Investigations

From the enediyne class of antitumor antibiotics, uncialamycin is among the rarest and most potent, yet one of the structurally simpler, making it attractive for chemical synthesis and potential applications in biology and medicine. In this article we describe a streamlined and practical enantioselective total synthesis of uncialamycin that is amenable to the synthesis of novel analogues and renders the natural product readily available for biological and drug development studies. Starting from hydroxy- or methoxyisatin, the synthesis features a Noyori enantioselective reduction, a Yamaguchi acetylide-pyridinium coupling, a stereoselective acetylide-aldehyde cyclization, and a newly developed annulation reaction that allows efficient coupling of a cyanophthalide and a p-methoxy semiquinone aminal to forge the anthraquinone moiety of the molecule. Overall, the developed streamlined synthesis proceeds in 22 linear steps (14 chromatographic separations) and 11% overall yield. The developed synthetic strategies and technologies were applied to the synthesis of a series of designed uncialamycin analogues equipped with suitable functional groups for conjugation to antibodies and other delivery systems. Biological evaluation of a select number of these analogues led to the identification of compounds with low picomolar potencies against certain cancer cell lines. These compounds and others like them may serve as powerful payloads for the development of antibody drug conjugates (ADCs) intended for personalized targeted cancer therapy.

Iron-Catalyzed Ortho C-H Methylation of Aromatics Bearing a Simple Carbonyl Group with Methylaluminum and Tridentate Phosphine Ligand

Iron-catalyzed C-H functionalization of aromatics has attracted widespread attention from chemists in recent years, while the requirement of an elaborate directing group on the substrate has so far hampered the use of simple aromatic carbonyl compounds such as benzoic acid and ketones, much reducing its synthetic utility. We describe here a combination of a mildly reactive methylaluminum reagent and a new tridentate phosphine ligand for metal catalysis, 4-(bis(2-(diphenylphosphanyl)phenyl)phosphanyl)-N,N-dimethylaniline (Me2N-TP), that allows us to convert an ortho C-H bond to a C-CH3 bond in aromatics and heteroaromatics bearing simple carbonyl groups under mild oxidative conditions. The reaction is powerful enough to methylate all four ortho C-H bonds in benzophenone. The reaction tolerates a variety of functional groups, such as boronic ester, halide, sulfide, heterocycles, and enolizable ketones.

Compounds for the treatment of metabolic disorders

Compounds useful for the treatment of various metabolic disorders, such as insulin resistance syndrome, diabetes, hyperlipidemia, fatty liver disease, cachexia, obesity, atherosclerosis and arteriosclerosis, are disclosed.