87860-36-4

Usage

Uses

Used in Agricultural and Environmental Science Research:
(+/-)-2-(3-chlorophenoxy)propionic acid is used as a research tool for studying the mode of action of synthetic auxins, specifically in the context of their impact on plant growth and development. Its ability to mimic the effects of 2,4-D makes it valuable for understanding how hormone signaling pathways are affected in plants.
Used in Herbicidal Agent Development:
(+/-)-2-(3-chlorophenoxy)propionic acid is also studied for its potential as a herbicidal agent. Its capacity to disrupt plant growth and development by interfering with hormone signaling pathways positions it as a candidate for the development of new herbicides, which could be used to control unwanted plant growth in agricultural settings.

Upstream product

• 101-10-0 2-(3-chlorophenoxy)propionic acid 
• 122623-81-8 methyl 2-(3-chlorophenoxy)propionate 
• 140146-14-1 (R)-methyl 2-(3-chlorophenoxy) propionate 
• 2362-28-9 m-chlorophenol, potassium salt 
• 1356837-77-8 (R,S)-2-(3-chlorophenoxy)propionyl 3-(2-pyridine)pyrazolide 
• 62784-66-1 bis(1-naphthyl)methanol 
• 4878-14-2 2-(3-Chloro-phenoxy)-propionyl chloride 
• 223799-38-0 (R)-2-(3-Chloro-phenoxy)-N-((S)-1-phenyl-ethyl)-propionamide 
• 109423-87-2 (R)-2-(3-Chloro-phenoxy)-propionic acid ethyl ester 

Downstream Products

• 92471-62-0 (R)-2-methyl-2-(3-chlorophenoxy)ethanol 

Relevant academic research and scientific papers

(R,S)-2-chlorophenoxyl pyrazolides as novel substrates for improving lipase-catalyzed hydrolytic resolution

The best reaction condition of Candida antartica lipase B as biocatalyst, 3-(2-pyridyl)pyrazole as leaving azole, and water-saturated methyl t-butyl ether as reaction medium at 45°C were first selected for performing the hydrolytic resolution of (R,S)-2-(4-chlorophenoxyl) azolides (1-4). In comparison with the kinetic resolution of (R,S)-2-phenylpropionyl 3-(2-pyridyl)pyrazolide or (R,S)-α-methoxyphenylacetyl 3-(2-pyridyl)pyrazolide at the same reaction condition, excellent enantioselectivity with more than two order-of-magnitudes higher activity for each enantiomer was obtained. The resolution was then extended to other (R,S)-3-(2-pyridyl)pyrazolides (5-7) containing 2-chloro, 3-chloro, or 2,4-dichloro substituent, giving good (E > 48) to excellent (E > 100) enantioselectivity. The thermodynamic analysis for 1, 2, and 4-7 demonstrates profound effects of the acyl or leaving moiety on varying enthalpic and entropic contributions to the difference of Gibbs free energies. A thorough kinetic analysis further indicates that on the basis of 6, the excellent enantiomeric ratio for 4 and 7 is due to the higher reactivity of (S)-4 and lower reactivity of (R)-7, respectively.

A new method for production of chiral 2-aryloxypropanoic acids using effective kinetic resolution of racemic 2-aryloxycarboxylic acids

We report a novel method for the preparation of 2-aryloxypropanoic acids by kinetic resolution of racemic 2-aryloxypropanoic acids using enantioselective esterification. The usage of pivalic anhydride (Piv2O) as an activating agent, bis(a-naphthyl)methanol ((α-Np)2CHOH) as an achiral alcohol, and (+)-benzotetramisole ((+)-BTM) as a chiral acyl-transfer catalyst enables the effective separation of various racemic 2-aryloxypropanoic acids to afford optically active carboxylic acids and the corresponding esters with high enantioselectivities. Furthermore, theoretical calculations of the transition states required to form the chiral esters successfully proved the enantiomer recognition mechanism of the asymmetric esterification.

Resolution of (±)-mandelic- and (±)-2-(chlorophenoxy)propionic-acid derivatives by crystallization of their diastereomeric amides with (R)- or (S)-α-arylethylamines

An alternative and cost effective route for the resolution in high ees (95-99%) of (±)-mandelic-and (±)-2-(chlorophenoxy)propionic- acid derivatives is reported. The key step involves the covalent derivatization and separation of their diastereomeric amides with (R)- or (S)-α- arylethylamines.

Optical resolution of aryloxypropionic acids and their esters by HPLC on cellulose tris-3,5-dimethyl-triphenylcarbamate derivative

Chiral chromatographic resolution of a series of antiphlogistic 2- aryloxypropionic acids and their methyl and ethyl esters was performed using a Chiralcel OD column. The CSP selected resolved most of the acids and esters efficiently, the enantiomers being well separated without requiring time consuming analysis. Chromatographic separation of R enriched samples was performed to determine the correct elution order. Using eluting systems such as hexane and 2-propanol, or hexane, 2-propanol and formic acid, the S enantiomer of all acids and esters was always found to elute first. We also considered the role of electron-donating or electron-withdrawing substituents (at the aryloxylic moiety) on the chiral resolution. It was shown that the electronic features of the substituents have more influence on the chiral interactions between the solutes and the CSP than their steric hindrance. Finally we determined, by molecular models, the interaction between CSP and solutes. In this way were able to determine all the potential sites for interactions, which are compatible with the conformations of the compounds and the structure of the stationary phase, and point out those interactions which enable chiral resolution.

Enzymatic enantioselective ester hydrolysis by carboxylesterase NP

The enzymatic hydrolysis of a series of carboxylic esters by carboxylesterase NP has been investigated in order to determine the scope and limitations of this enzyme. 2-Substituted propionates were hydrolyzed with high enantioselectivity when an aromatic moiety was part of the 2-substituent.Enantioselective hydrolysis could be accomplished with several 2-arypropionates, 2-(aryloxy)propionates and N-arylalanine esters.The propionate esters yielded propionic acids as (S) enantiomers, whereas the alanine esters yielded the (R) enantiomers.Without a 2-aryl substituent, the enzymatic hydrolysis of the propionates occurred at a lower rate without acceptable enantioselectivity.In addition to 2-substituted propionates, only a few other esters were hydrolyzed with high enantioselectivity by carboxylesterase NP, such as some prochiral disubstituted malonates. 1-Phenylethylacetate was the only substrate with chirality in the alcohol part of the ester that was found to be hydrolyzed enantioselectively.Carboxylesterase NP proved to be a powerful enzyme for kinetic resolution of propionate esters with an aromatic ring containing a 2-substituent.

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.

Enzyme catalysed hydrolysis of chlorophenoxypropionates

We report on the enzymatic hydrolysis of methyl 2-phenoxypropionate and of the following chlorinated derivatives: methyl o-chloro-, m-chloro-, p-chloro-, and o,p-dichloro-2-phenoxypropionates. α-Chymotripsyn, lipase, and pig liver esterase have an R enantioselectivity whereas subtilisin has an S enantioselectivity.Enantiomeric excess (e.e.) cover a wide range (from 5 to 100percent).