71301-98-9

Basic information

• Product Name: Ethyl (R)-(+)-2-(4-hydroxyphenoxy)propionate
• Synonyms: Ethyl(R)-(+)-2-(4-hydroxyphenoxy)propanoate;(R)-ethyl 2-(4-hydroxyphenoxy)propanoate;(R)-2-(4-Hydroxyphenoxy)propionic acid ethyl ester;(R)-2-(p-Hydroxyphenoxy)propionic acid ethyl ester
• CAS NO: 71301-98-9
• Molecular Formula: C₁₁H₁₄O₄
• Molecular Weight: 210
• Mol File: 71301-98-9.mol
• Article Data: 4

Chemical Properties

• Melting Point: 36-37℃
• Boiling Point: 327℃
• Flash Point: 124℃
• Appearance: /
• Density: 1.156
• Vapor Pressure: 0.000106mmHg at 25°C
• Refractive Index: 1.518
• Storage Temp.: 2-8°C
• PKA: 10.09±0.15(Predicted)
• CAS DataBase Reference: Ethyl (R)-(+)-2-(4-hydroxyphenoxy)propionate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl (R)-(+)-2-(4-hydroxyphenoxy)propionate(71301-98-9)
• EPA Substance Registry System: Ethyl (R)-(+)-2-(4-hydroxyphenoxy)propionate(71301-98-9)

Safety Data

• Hazardous Substances Data: 71301-98-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Ethyl (R)-(+)-2-(4-hydroxyphenoxy)propionate is used as an intermediate in the synthesis of pharmaceuticals for its specific chiral properties. Ethyl (R)-(+)-2-(4-hydroxyphenoxy)propionate's unique arrangement of atoms allows for the creation of enantiomerically pure drugs, which is essential for ensuring the desired biological activity and minimizing potential side effects.
Used in Agrochemical Industry:
In the agrochemical industry, Ethyl (R)-(+)-2-(4-hydroxyphenoxy)propionate is used as a building block for the development of chiral agrochemicals. Its enantiomeric purity ensures that the synthesized compounds exhibit the desired biological activity and selectivity, reducing the risk of unintended environmental impacts.
Used in Flavor and Fragrance Industry:
Ethyl (R)-(+)-2-(4-hydroxyphenoxy)propionate is used as a key component in the production of flavor and fragrance compounds. Its fruity, floral odor makes it a valuable ingredient in creating various scents and flavors for the food, beverage, and cosmetics industries.
Used in Organic Synthesis:
As a chiral ester, Ethyl (R)-(+)-2-(4-hydroxyphenoxy)propionate is widely used in organic synthesis for the preparation of various chiral compounds. Its specific three-dimensional arrangement of atoms allows for the selective formation of enantiomerically pure products, which is crucial in many chemical reactions and applications.

InChI:InChI=1/C11H14O4/c1-3-14-11(13)8(2)15-10-6-4-9(12)5-7-10/h4-8,12H,3H2,1-2H3/t8-/m1/s1

Upstream product

• 123-31-9 hydroquinone 
• 535-13-7 2-chloro-propanoic acid, ethyl ester 
• 65343-67-1 ethyl 2-(4-hydroxyphenoxy)propanoate 
• 66441-23-4 fenoxaprop-p-ethyl 
• 131775-56-9 (R)-2-(p-acetylphenoxy)propionic acid ethyl ester 
• 74497-15-7 (L) Ethyl 2-chloropropanoate 
• 2516-47-4 cyclopropanemethylamine 
• 765-30-0 Cyclopropylamine 
• 2620-50-0 1,3-benzodioxol-5-ylmethyl amine 
• 3731-53-1 4-(aminomethyl)pyridine 
• 3731-52-0 3-Aminomethylpyridine 
• 3731-51-9 2-(Aminomethyl)pyridine 

Downstream Products

• 66441-23-4 fenoxaprop-p-ethyl 
• 113776-20-8 (-)-ethyl (2S)-2-[4-[(6-chloro-2-benzoxazolyl)oxy]phenoxy]propanoate 
• 122008-78-0 cyhalofop-butyl 
• 94050-90-5 (R)-2-(4-hydroxyphenoxy)propionic acid 

Relevant articles and documents

Resolution of (R, S)-ethyl-2-(4-hydroxyphenoxy) propanoate using lyophilized mycelium of Aspergillus oryzae WZ007

The mycelium of Aspergillus oryzae WZ007 was successfully developed to kinetic resolution of (R, S)-ethyl-2-(4-hydroxyphenoxy) propanoate ((R, S)-EHPP) for production of (R)-ethyl-2-(4-hydroxyphenoxy) propanoate ((R)-EHPP). The key biocatalytic process parameters (pH, temperature, rotation speed and substrate concentration) were optimized. Under the optimum conditions, the optical purity of (R)-EHPP was improved up to >99% when the conversion was above 49%. A. oryzae WZ007 whole-cell lipase exhibited high reaction capacity, enantioselectivity and good reusability. The tolerable substrate concentration was 0.5 mol/L, and dry mycelium of A. oryzae WZ007 maintains over 80% of its initial activity after eight repeating cycles. Therefore the enzymatic preparation of (R)-EHPP route was suitable for industrial application.

Spectrophotometric method for quantification of fenoxaprop-p-ethyl herbicide in commercial formulations and agricultural samples

A simple spectrophotometric method was developed for determination of fenoxaprop-p-ethyl herbicide in agricultural samples. The method is based on the acid hydrolysis of fenoxaprop-pethyl to form 6-chloro-2,3-dihydrobenzoxazol-2- one (CDHB) and ethyl 2-(4-hydroxyphenoxy) propionate (EHPP). The 6-chloro-2,3- dihydrobenzoxazol-2-one was used as a coupling reagent in diazotization reaction. The absorbance of the azo dye was measured at 430 nm. The reaction conditions were optimized for hydrolysis as well as for the diazotization reaction. The Beer's law was obeyed over the concentration range of 0.2-25 μg mL-1 with molar absorptivity of 1.4 × 104L mol -1 cm-1. The limit of detection (LOD) and limit of quantification (LOQ) were found to be 0.029 and 0.098g μg mL-1, respectively The method has been successfully applied to the determination of fenoxaprop-p-ethyl commercial formulations and various agricultural samples. The % recoveries were found in the range of 95-97%.

A PROCESS FOR OPTICAL PURE (R)-2-PHENOXYPROPIONIC ACID DERIVATIVES

The present invention relates to a method for manufacturing optically active (R)-2-phenoxypropionic acid derivatives. More particularly, the present invention relates to a method for manufacturing optically active (R)-2-phenoxypropionic acid derivatives with high purity by using p-substituted phenol derivatives and alkyl (S)-2-arylsulfonyloxypropionate as starting materials and reacting them at 60 to 100 °C in the presence of an alkalimetal salt as a base and. a hydrocarbon solvent.

Synthesis of optically active 2-[4-(6-chloro-2-benzoxazolyloxy) phenoxy]propionamide derivatives of potential herbicide activity

An efficient two steps procedure has been developed for the synthesis of (R)-(+)-2-[4-(6-chloro-2-benzoxazolyloxy)phenoxy]propionamides (8a-f) starting from (R)-(+)-methyl 2-(4-hydroxyphenoxy)-propionate (4). Treatment of R-(+)-2 with the primary amines 5a-f resulted in 9a-f quantitatively instead of a desired amidation [R-(+)-2 → R-(+)-8a-f]. This unexpected transformation was discussed on the basis of QM calculation.