2786-19-8

Basic information

• Product Name: MECOPROP METHYL ESTER
• Synonyms: (+/-)-2-(4-CHLORO-O-TOLYLOXY)-PROPIONIC ACID METHYLESTER;2-(4-CHLORO-2-METHYLPHENOXY)-PROPANOIC ACID METHYL ESTER;MECOPROP METHYL ESTER;MCPP METHYL ESTER;MCPP METHYL ESTER 1X1ML HEX 2000 UG/ML;MECOPROP-METHYL ESTER PESTANAL 250 MG;MECOPROP-METHYL ESTER PESTANAL;MECOPROP METHYL ESTER, 100MG, NEAT
• CAS NO: 2786-19-8
• Molecular Formula: C11H13ClO3
• Molecular Weight: 228.67
• Product Categories: MA - MDEPA;8000 Series Solidwaste Methods;Alpha sort;H-MAlphabetic;M;Method 8150/8151;Pesticides&Metabolites
• Mol File: 2786-19-8.mol

Chemical Properties

• Boiling Point: 294.2°Cat760mmHg
• Flash Point: 100 °C
• Appearance: /Solid
• Density: 1.172g/cm³
• Vapor Pressure: 0.005mmHg at 25°C
• Refractive Index: n20/D 1.52
• Storage Temp.: 0-6°C
• BRN: 2455097
• CAS DataBase Reference: MECOPROP METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: MECOPROP METHYL ESTER(2786-19-8)
• EPA Substance Registry System: MECOPROP METHYL ESTER(2786-19-8)

Safety Data

• Hazard Codes: Xn,N,F
• Statements: 22-43-50/53-67-65-62-51/53-48/20-38-11
• Safety Statements: 13-36/37-60-61-62
• RIDADR: UN 3082 9/PG 3
• WGK Germany: 3
• Hazardous Substances Data: 2786-19-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H11ClO3/c1-7(10(12)13-2)14-9-5-3-8(11)4-6-9/h3-7H,1-2H3

Upstream product

• 17639-93-9 2-chloro-propionic acid methyl ester 
• 52106-86-2 sodium 4-chloro-2-methyl-phenolate 
• 23844-56-6 methyl R-2-(4-chloro-2-methylphenoxy)propanoate 
• 247942-96-7 methyl (S)-2-fluorosulfonyloxypropanoate 
• 1570-64-5 2-methyl-4-chlorophenol 
• 5445-17-0 Methyl 2-bromopropionate 

Relevant articles and documents

Evaluation of the Edman degradation product of vancomycin bonded to core-shell particles as a new HPLC chiral stationary phase

A modified macrocyclic glycopeptide-based chiral stationary phase (CSP), prepared via Edman degradation of vancomycin, was evaluated as a chiral selector for the first time. Its applicability was compared with other macrocyclic glycopeptide-based CSPs: TeicoShell and VancoShell. In addition, another modified macrocyclic glycopeptide-based CSP, NicoShell, was further examined. Initial evaluation was focused on the complementary behavior with these glycopeptides. A screening procedure was used based on previous work for the enantiomeric separation of 50 chiral compounds including amino acids, pesticides, stimulants, and a variety of pharmaceuticals. Fast and efficient chiral separations resulted by using superficially porous (core-shell) particle supports. Overall, the vancomycin Edman degradation product (EDP) resembled TeicoShell with high enantioselectivity for acidic compounds in the polar ionic mode. The simultaneous enantiomeric separation of 5 racemic profens using liquid chromatography-mass spectrometry with EDP was performed in approximately 3?minutes. Other highlights include simultaneous liquid chromatography separations of rac-amphetamine and rac-methamphetamine with VancoShell, rac-pseudoephedrine and rac-ephedrine with NicoShell, and rac-dichlorprop and rac-haloxyfop with TeicoShell.

Synthesis and biological evaluation of novel Ani9 derivatives as potent and selective ANO1 inhibitors

Anoctamin 1 (ANO1), a calcium-activated chloride channel, is highly expressed and amplified in a number of carcinomas including breast, pancreatic and prostate cancers. Downregulation of ANO1 expression and function significantly inhibits cell proliferation, migration, and invasion of various cancer cell lines. Development of potent and selective ANO1 inhibitors is currently desirable, which may provide a new strategy for cancer treatment. Our previous study revealed a new class of ANO1 inhibitor, (E)-2-(4-chloro-2-methylphenoxy)-N'-(2-methoxybenzylidene)acetohydrazide (Ani9) and structural optimization via chemical modification of Ani9 basic skeleton was undertaken for the development of more potent and specific inhibitors of ANO1. Structure-activity relationship studies with newly synthesized derivatives revealed a number of potent ANO1 inhibitors, among which 5f is the most potent inhibitor with an IC50 value of 22 nM. The selectivity analyses showed that 5f has excellent selectivity to ANO1 (>1000-fold over ANO2). In cellular assays, 5f significantly inhibited cell proliferation of PC3, MCF7, and BxPC3 cells expressing high levels of ANO1. In addition, 5f strongly reduced the protein levels of ANO1 in PC3 cells. This study will be useful in the development of ANO1 inhibitors for treatment of cancer and other ANO1-related diseases.

Insight into solid-liquid phase transfer catalyzed synthesis of Mecoprop ester using K 2CO 3 as base and development of new kinetic model involving liquid product and two solid co-products

Abstract: 2-Methyl-4-chlorophenoxy propionic acid (Mecoprop) is a widely used household herbicide. In the current work, a simple synthetic method is developed for Mecoprop methyl ester using solid-liquid phase transfer catalysis (S-L PTC) with K 2CO 3 as mild base and toluene as solvent. Conversion of 95% was achieved with 100% selectivity for Mecoprop ester at 100°C. Simple isolation process was employed to recover the product from the reaction mixture. A reaction mechanism was proposed and new kinetic model developed involving one liquid and two solid co-products. The activation energy for the reaction was calculated. This is the first example of its kind being reported vis-à-vis kinetics and mechanism. Graphical Abstract: Solid-liquid phase transfer catalyzed (S-L PTC) O-alkylation of 4-chloro-2-methyl phenol is done at relatively mild conditions to form methyl 2-(4-chloro-2-methylphenoxy) propionate (Mecoprop methyl ester). New insight on reaction mechanism and kinetics is presented.

Conversion of a hydroxy group in certain alcohols into a fluorosulfonate ester or a trifluoromethylsulfonate ester

The present invention provides a method of converting a hydroxy group in alcohols containing an electron withdrawing group into perfluoroalkane sulfonate and fluorosulfonate esters, which are good leaving groups, with inversion of configuration where the hydroxyl-bearing carbon is chiral. The method consists of converting an alcohol to an O—N,N-dialkylsulfamate ester and reacting it with a perfluoroalkansulfonic or fluorosulfonic acid. The method has applications in the synthesis of pharmaceutical and agrochemical compounds.

Enantioselective inhibition: a strategy for improving the enantioselectivity of biocatalytic systems

Dextromethorphan (DM) and levomethorphan (LM) were found to be effective enantioselective inhibitors of Candida cylindracea lipase-catalyzed hydrolysis of a variety of (±)-arlypropionic and (±)-(arloxy)propionic esters. The enantioselectivity of the biocatalytic resolution of (±)-methyl 2-(2,4-dichlorophenoxy)propionate (DCPP) was enhanced 20-fold in the presence of either DM or LM. A general model for enantioselective inhibition has been developed, and a quantitative expression has been derived to show the underlying parameters that govern enantioselective inhibition. To define the mechanism of action of DM, a series of kinetic inhibition experiments was conducted with enantiomerically pure (R)-(+)-DCPP and (S)-(-)-DCPP. The observed inhibition pattern was that of partial noncompetitive inhibition for (R)-(+)-DCPP and that of pure noncompetitive inhibition for (S)-(-)-DCPP.

Preparation of aliphatic/aromatic ethers

Aliphatic/aromatic ethers are prepared by reacting an aliphatic halide with either an alkali or alkaline earth metal, or ammonium phenolate or naphtholate, in an inert organic solvent, and in the presence of at least one tertiary amine sequestering agent having the formula: