87860-36-4

Basic information

• Product Name: (+/-)-2-(3-chlorophenoxy)propionic acid
• CAS NO: 87860-36-4
• Molecular Formula: C₉H₉ClO₃
• Molecular Weight: 200.62
• Mol File: 87860-36-4.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (+/-)-2-(3-chlorophenoxy)propionic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-2-(3-chlorophenoxy)propionic acid(87860-36-4)
• EPA Substance Registry System: (+/-)-2-(3-chlorophenoxy)propionic acid(87860-36-4)

Safety Data

• Hazardous Substances Data: 87860-36-4(Hazardous Substances Data)

Usage

Description

(+/-)-2-(3-chlorophenoxy)propionic acid, a chemical compound with the molecular formula C9H9ClO3, is a derivative of the herbicide 2,4-dichlorophenoxyacetic acid (2,4-D). It is often utilized as a biochemical tool to investigate the effects of 2,4-D on plant growth and development. (+/-)-2-(3-chlorophenoxy)propionic acid is known to mimic the effects of 2,4-D, disrupting hormone signaling pathways and thereby interrupting the growth and development of plants.

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

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

Downstream Products

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

Relevant articles and documents

(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.

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.

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.