32189-36-9

Basic information

• Product Name: (R)-2-(4-Chlorophenyl)-2-hydroxyethanoic acid
• Synonyms: RARECHEM AL BO 1451;(R)-4-CHLOROMANDELIC ACID;R-(-)-4-CHLOROMANDELIC ACID;(r)-2-(4-chlorophenyl)-2-hydroxyethanoic acid;(2r)-2-(4-chlorophenyl)-2-hydroxyacetic acid;(R)-2-(2-CHLOROPHENYL)-GLYCINE;(R)-2-(4-Chlorophenyl)-2-hydroxyacetic acid;D-4-chloro Mandelic acid
• CAS NO: 32189-36-9
• Molecular Formula: C₈H₇ClO₃
• Molecular Weight: 186.59
• Mol File: 32189-36-9.mol
• Article Data: 45

Chemical Properties

• Melting Point: 108°C
• Boiling Point: 361°C
• Flash Point: 172°C
• Appearance: /
• Density: 1.468
• Vapor Pressure: 7.43E-06mmHg at 25°C
• Refractive Index: 1.605
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: soluble in Methanol
• PKA: 3.14±0.10(Predicted)
• BRN: 2692851
• CAS DataBase Reference: (R)-2-(4-Chlorophenyl)-2-hydroxyethanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-(4-Chlorophenyl)-2-hydroxyethanoic acid(32189-36-9)
• EPA Substance Registry System: (R)-2-(4-Chlorophenyl)-2-hydroxyethanoic acid(32189-36-9)

Safety Data

• Hazard Codes: Xn
• Statements: 41-42/43
• Safety Statements: 22-26-36/37/39-45
• WGK Germany: 3
• Hazardous Substances Data: 32189-36-9(Hazardous Substances Data)

Usage

Description

(R)-2-(4-Chlorophenyl)-2-hydroxyethanoic acid, also known as (R)-2-(4-chlorophenyl)glycolic acid, is a chiral organic compound with the molecular formula C8H7ClO3. It is characterized by its white to off-white powder form and its sparing solubility in water. As an intermediate in the synthesis of pharmaceuticals and agrochemicals, this compound plays a crucial role in the production of various synthetic organic compounds, making it a significant entity in the realm of organic chemistry and drug development.

Uses

Used in Pharmaceutical Industry:
(R)-2-(4-Chlorophenyl)-2-hydroxyethanoic acid is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the development of new drugs. Its unique chiral structure allows for the creation of enantiomer-specific medications, which can have different biological activities and reduce potential side effects.
Used in Agrochemical Industry:
In the agrochemical sector, (R)-2-(4-Chlorophenyl)-2-hydroxyethanoic acid is utilized as an intermediate in the production of agrochemicals, such as pesticides and herbicides. Its role in these applications is to enhance the effectiveness and selectivity of these chemicals, contributing to more efficient and targeted agricultural solutions.
Used in Organic Synthesis:
(R)-2-(4-Chlorophenyl)-2-hydroxyethanoic acid is used as a building block in organic synthesis for its versatility in forming a wide range of synthetic organic compounds. This makes it an essential component in the creation of new materials and molecules with potential applications across various industries.

InChI:InChI=1/C8H7ClO3/c9-6-3-1-5(2-4-6)7(10)8(11)12/h1-4,7,10H,(H,11,12)/t7-/m1/s1

Upstream product

• 14062-24-9 4-chloro-benzeneacetic acid, ethyl ester 
• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 7138-34-3 p-chloromandelic acid 
• 106-39-8 bromochlorobenzene 
• 201230-82-2 carbon monoxide 
• 1878-66-6 4-chlorophenylacetic Acid 
• 79-36-7 dichloroacethyl chloride 
• 108-90-7 chlorobenzene 
• 13312-83-9 4-chloromandelonitrile 
• 13651-12-2 2,2-dibromo-1-(4-chlorophenyl)ethanone 
• 102767-28-2 levetiracetam 
• 74590-69-5 4-chloro-α-fluorobenzeneacetic acid 
• 99-91-2 para-chloroacetophenone 
• 37542-28-2 methyl (p-chlorphenyl)glyoxylate 

Downstream Products

• 83-05-6 bis(4'-chlorophenyl)acetic acid 
• 492-86-4 (R)-4-chloro-α-hydroxy-benzeneacetic acid 
• 74-11-3 para-chlorobenzoic acid 
• 76496-63-4 (S)-4-chloro-α-hydroxy-benzeneacetic acid 
• 1217298-38-8 C₈H₇ClO₃*C₁₀H₁₅OP 
• 1217298-40-2 C₈H₇ClO₃*C₁₀H₁₅OP 
• 164293-06-5 (R)-1-phenylethanaminium (R)-4-chloromandelate 
• 1131311-98-2 (R)-PEA*(S)-p-ClMA 
• 32174-34-8 methyl 4-chloromandelate 
• 121216-27-1 N-(7-hydroxy-1,2,3,4-tetrahydronaphth-2-yl)-4-chloromandelamide 
• 75188-06-6 2-chloro-2-(4-chlorophenyl)acetyl chloride 
• 18584-27-5 2-(4-chlorophenyl)-2-hydroxyacetamide 
• 106963-36-4 Na salt of N-(p-chloro-mandelyl)-4-amino-lactivinic acid 
• 90390-88-8 (6S,10bS)-6-(4-Chloro-phenyl)-2,3,6,10b-tetrahydro-1H-pyrrolo[2,1-a]isoquinolin-5-one 

Relevant articles and documents

Enantioselective resolution of 4-chloromandelic acid by liquid–liquid extraction using 2-chloro-N-carbobenzyloxy-L-amino acid

A liquid–liquid extraction resolution of 4-chloro-mandelic acid (4-ClMA) was studied by using 2-chloro-N-carbobenzyloxy-L-amino acid (2-Cl-Z-AA) as a chiral extractant. Important factors affecting the extraction efficiency were investigated, including the type of chiral extractant, pH value of aqueous phase, initial concentration of chiral extractant in organic phase, initial concentration of 4-ClMA in aqueous phase, and resolution temperature. It was observed that the concentration of (R)-4-ClMA was much higher than that of (S)-4-ClMA in organic phase due to a higher stability of the complex formed between (R)-4-ClMA and 2-Cl-Z-AA. A separation factor (α) of 3.05 was obtained at 0.02 mol/L 2-Cl-Z-Valine dissolved in dichloromethane, pH of 2.0, concentration of 4-ClMA of 0.11 mmol/Land T of 296.7K.

Synthesis of α-hydroxycarboxylic acids from various aldehydes and ketones by direct electrocarboxylation: A facile, efficient and atom economy protocol

In present work, the formation of α-hydroxycarboxylic acids have been described from various aromatic aldehydes and ketones via direct electrocarboxylation method with 80-92% of yield without any side product and can be purified by simple recrystallization using sacrificial Mg anode and Pt cathode in an undivided cell, CO2at (1 atm) was continuously bubbled in the cell throughout the reaction using tetrapropylammonium chloride as a supporting electrolyte in acetonitrile. The synthesized compounds obtained in fair to excellent yield with a high level of purity. The characterization of electrocarboxylated compounds was done with spectroscopic techniques like IR, NMR (1H & 13C), mass and elemental analysis.

Enantioseparation of chiral mandelic acid derivatives by supercritical fluid chromatography

Mandelic acid and its derivatives are important chiral analogs which are widely used in the pharmaceutical synthetic industry. The present study investigated the enantiomeric separation of six mandelic acids (mandelic acid, 2-chloromandelic acid, 3-chloromandelic acid, 4-chloromandelic acid, 4-bromomandelic acid, 4-methoxymandelic acid) on the Chiralpak AD-3 column by supercritical fluid chromatography. The influences of volume fraction of trifluoroacetic acid, type and percentage of modifier, column temperature, and backpressure on the separation efficiency were investigated. And the enantiomer elution order was determined. The results show that, for a given modifier, the retention factor, the separation factor, and the separation resolution decreased gradually with increasing the volume ratio of the modifier. At the same volume ratio of modifier, the retention factor of the mandelic acid and its derivatives increased in the order of methanol, ethanol, and isopropanol, except 3-chloromandelic acid. The separation factor and the separation resolution decreased with the increase of column temperature (below the temperature limit). The backpressure affected the enantioseparation process: As the backpressure increased, a corresponding decrease in retention factor was observed. Under the same chiral column conditions, the SFC method exhibited faster and more efficient separation with better enantioselectivity than the HPLC method.