63640-09-5

Basic information

• Product Name: (R)-2-(4-CHLORO-PHENYL)-3-METHYL-BUTYRIC ACID
• Synonyms: (R)-2-(4-CHLORO-PHENYL)-3-METHYL-BUTYRIC ACID;(R)-2-(4-Chlorophenyl)-3-Methylbutanoic acid
• CAS NO: 63640-09-5
• Molecular Formula: C₁₁H₁₃ClO₂
• Molecular Weight: 212.675
• Mol File: 63640-09-5.mol

Chemical Properties

• Boiling Point: 318.7°C at 760 mmHg
• Flash Point: 146.5°C
• Appearance: /
• Density: 1.184g/cm³
• Vapor Pressure: 0.000148mmHg at 25°C
• Refractive Index: 1.537
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: (R)-2-(4-CHLORO-PHENYL)-3-METHYL-BUTYRIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-(4-CHLORO-PHENYL)-3-METHYL-BUTYRIC ACID(63640-09-5)
• EPA Substance Registry System: (R)-2-(4-CHLORO-PHENYL)-3-METHYL-BUTYRIC ACID(63640-09-5)

Safety Data

• Hazardous Substances Data: 63640-09-5(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(R)-2-(4-CHLORO-PHENYL)-3-METHYL-BUTYRIC ACID is used as a building block in organic synthesis for the creation of various compounds, leveraging its unique molecular structure to form new chemical entities with potential applications across different industries.
Used in Pharmaceutical Research:
In the pharmaceutical industry, (R)-2-(4-CHLORO-PHENYL)-3-METHYL-BUTYRIC ACID is utilized as a key component in the development of new drugs. Its specific stereochemistry and structural features make it a valuable asset in medicinal chemistry, potentially leading to the discovery of novel therapeutic agents.
Used in Drug Design:
(R)-2-(4-CHLORO-PHENYL)-3-METHYL-BUTYRIC ACID's (R)-configuration is significant in drug design, as it may influence the molecule's interactions with biological targets, such as enzymes or receptors. This aspect is crucial for the development of drugs with high selectivity and potency, minimizing side effects and improving treatment outcomes.
Used in Biological Research:
(R)-2-(4-CHLORO-PHENYL)-3-METHYL-BUTYRIC ACID may also have potential biological or pharmacological activity, making it a valuable tool in biological research. Its unique structure can be used to probe the mechanisms of biological processes and to identify new targets for therapeutic intervention.

InChI:InChI=1/C11H13ClO2/c1-7(2)10(11(13)14)8-3-5-9(12)6-4-8/h3-7,10H,1-2H3,(H,13,14)/t10-/m1/s1

Upstream product

• 2012-81-9 3-Methyl-2-(4'-chlorophenyl)-butyronitrile 
• 5096-11-7 (S)-3-(1-hydroxyethyl)pyridine 
• 51631-99-3 2-(4-Chlorphenyl)-3-methylbuttersaeureanhydrid 
• 27854-88-2 (R)-1-(4-pyridinyl)ethanol 
• 74408-48-3 2-(4-Chlorophenyl)-3-methylbutyraldehyde 
• 106-43-4 para-chlorotoluene 
• 1878-66-6 4-chlorophenylacetic Acid 
• 75-29-6 isopropyl chloride 
• 51631-50-6 2-(4-chlorophenyl)-3-methyl-(2SR)-butanoyl chloride 
• 66230-04-4 esfenvalerate 
• 86618-06-6 methyl 2-(4-chlorophenyl)-3-methylbutanoate 
• 33131-40-7 2-(4-chlorophenyl)-3-methylcrotonic acid 
• 2012-74-0 2-(4-chlorophenyl)-3-methylbutyric acid 
• 2627-86-3 (S)-1-phenyl-ethylamine 

Downstream Products

• 51631-50-6 2-(4-chlorophenyl)-3-methyl-(2SR)-butanoyl chloride 
• 55332-38-2 S-isopropyl-4-chlorophenylacetic acid 
• 69741-69-1 2-(4-chlorophenyl)-3-methylbutyramide 
• 86618-06-6 methyl 2-(4-chlorophenyl)-3-methylbutanoate 
• 916074-16-3 2-(4-chloro-phenyl)-3-methyl-butyryl isocyanate 
• 67614-32-8 (R)-α-cyano-3-phenoxybenzyl (S)-2-(4-chlorophenyl)-3-methylbutyrate 
• 67614-33-9 (R)-α-cyano-3-phenoxybenzyl (R)-2-(4-chlorophenyl)isovalerate 
• 66230-04-4 esfenvalerate 
• 66267-77-4 [R]-alpha-cyano-3-phenoxybenzyl [S]-2-(4-chlorophenyl)-2-isopropyl-acetate 
• 223905-29-1 N-[(S)-4-chloro-α-(1-methylethyl)benzeneacetyl]4-nitro-L-phenylalanine 

Relevant articles and documents

Enantioselective Hydrogenation of Tetrasubstituted α,β-Unsaturated Carboxylic Acids Enabled by Cobalt(II) Catalysis: Scope and Mechanistic Insights

Chiral carboxylic acids are important compounds because of their prevalence in pharmaceuticals, natural products and agrochemicals. Asymmetric hydrogenation of α,β-unsaturated carboxylic acids has been widely recognized as one of the most efficient synthetic approaches to afford such compounds. Although related asymmetric hydrogenation of di- and trisubstituted unsaturated acids with noble metals is well established, asymmetric hydrogenation of challenging tetrasubstituted α,β-unsaturated carboxylic acids is rarely reported. We demonstrate enantioselective hydrogenation of cyclic and acyclic tetrasubstituted α,β-unsaturated carboxylic acids via cobalt(II) catalysis. This protocol showed broad substrate scope and gave chiral carboxylic acids in good yields with excellent enantiocontrol (up to 98 % yield and 99 % ee). Combined experimental and computational mechanistic studies support a CoII catalytic cycle involving migratory insertion and σ-bond metathesis processes. DFT calculations reveal that enantioselectivity may originate from the steric effect between the phenyl groups of the ligand and the substrate.

Screening of by-products of esfenvalerate in aqueous medium using SBSE probe desorption GC-IT-MS technique

The pyrethroids, their metabolites and by-products have been recognized as toxic to environment and human health. Despite several studies about esfenvalerate toxicity and its detection in water and sediments, information about its degradation products is still scanty. In this work, esfenvalerate degradation products were obtained by chemical oxidation with hydrogen peroxide and their structure was elucidated using a procedure known as stir bar sorptive extraction (SBSE) probe desorption gas chromatography-ion trap mass spectrometry (GC-IT-MS) analysis. This procedure consists of the thermal desorption of analytes extracted from a SBSE stir bar introduced by a probe into a gas chromatograph (GC) coupled to an ion trap mass spectrometry (IT-MS) system. Based on IT-MS data, a degradation pathway of esfenvalerate is proposed with ten products of chemical oxidation of esfenvalerate that are fully identified. Among these compounds, 3-phenoxybenzoic acid and 3-phenoxybenzaldehyde were detected, reported as being environmental metabolites of some pyrethroids, with endocrine-disrupting activity.

Iridium-catalyzed enantioselective hydrogenation of α,β- unsaturated carboxylic acids with tetrasubstituted olefins

A highly efficient asymmetric hydrogenation of α,β-unsaturated carboxylic acids with tetrasubstituted olefin catalyzed by chiral spiro iridium complexes has been developed for the preparation of chiral α-substituted carboxylic acids in excellent enantioselectivities (up to 99% ee).

The first synthetic agonists of FFA2: Discovery and SAR of phenylacetamides as allosteric modulators

Free fatty acid receptor 2 (FFA2) is a G-protein coupled receptor for which only short-chain fatty acids (SCFAs) have been reported as endogenous ligands. We describe the discovery and optimization of phenylacetamides as allosteric agonists of FFA2. These novel ligands can suppress adipocyte lipolysis in vitro and reduce plasma FFA levels in vivo, suggesting that these allosteric modulators can serve as pharmacological tools for exploring the potential function of FFA2 in various disease conditions.

Enantioselective extraction of fenvaleric acid enantiomers by two-phase (W/O) recognition chiral extraction

To establish an extraction method for fenvaleric acid (FA) enantiomers using l-iso-butyl-l-tartaric esters and hydroxypropyl-β-cyclodextrin (HP-β-CD) as chiral selector, the distribution of FA enantiomers was examined in methanol aqueous solution containing HP-β-CD and 1,2-dichloroethane organic solution containing l-iso-butyl-l-tartaric esters. The influences of the concentration of l-iso-butyl-l-tartaric esters and HP-β-CD, organic diluent, pH, extraction temperature and the concentration of methanol aqueous solution on the partition coefficient (k) and separation factor (α) of FA were investigated. The experiment results showed that the complex formed by l-iso-butyl-l-tartaric esters with S-enantiomer is stabler than that with R-enantiomer. With the increase of the concentration of l-iso-butyl-l-tartaric ester, k and α increased; With the increase of the concentration of HP-β-CD, k increased firstly, and then decreased, but α increased all the while, k was the highest when the concentration of HP-β-CD was 4 mmol L-1. 1,2-dichloroethane organic diluent was better than the others. With the increase of pH, k and α decreased; with further increasing concentration of methanol aqueous solution, k and α decreased, k and α were the highest when the concentration of methanol aqueous solution was 10%. The extraction temperature had a great influence on k and α, too.

Purification and characterization of a novel pyrethroid hydrolase from Aspergillus niger ZD11

The pyrethroid pesticides residues on foods and environmental contamination are a public safety concern. Pretreatment with pyrethroid hydrolase has the potential to alleviate the conditions. For this purpose, a fungus capable of using pyrethroid pesticides as a sole carbon source was isolated from the soil and characterized as Aspergillus niger ZD11. A novel pyrethroid hydrolase from cell extract was purified 41.5-fold to apparent homogeneity with 12.6% overall recovery. It is a monomeric structure with a molecular mass of 56 kDa, a pl of 5.4, and the enzyme activity was optimal at 45°C and pH 6.5. The activities were strongly inhibited by Hg2+, Ag+, and p-chloromercuribenzoate, whereas less pronounced effects (5-10% inhibition) were observed in the presence of the remaining divalent cations, the chelating agent EDTA and phenanthroline. The purified enzyme hydrolyzed various insecticides with similar carboxylester. trans-Permethrin is the preferred substrate.

PROCESS FOR PREPARING (+)-2-(4-CHLOROPHENYL)-3-METHYL BUTANOIC ACID

The present invention relates to an environmentally benign process for preparation of (+)2-(4-chlorophenyl)-3-methyl butanoic acid (+ CPA) from its racemic acid, using optically active arylamines like (-) PEA in hydrophilic/hydrophobic organic solvents like butanol, propanol etc. as aqueous mixtures, separating the desired (+) CPA salt, mother liquor by filtration and refining the (+) CPA salt in the same solvent system as used for resolution, recovering the desired acid in high optical purity by extracting with aqueous mineral acid. The mother liquor is concentrated under vacuum and extracted with aqueous mineral acid to obtain undesired (-) CPA which was recovered and recycled after racemization. The aqueous mineral acid layer thus obtained is mixed with corresponding aqueous mineral acid layer obtained from (+) CPA recovery and extracted with aqueous caustic lie solution to recover the optically active amine used for resolution. Thus the method described effectively provides a process for recovery and recycle of the undesired (-) CPA, optically active amine, besides obtaining the desired (+) CPA in high optical purity.

A Rearrangement Route to Fenvaleric Acid

(±)-Fenvaleric acid 2, the key intermediate for the preparation of the pesticide esfenvalerate 1, was prepared by a novel sequence which first involves the Henry reaction of 2-methyl-1-nitropropane and 4-chlorobenzaldehyde. The nitroaldol reaction provided nitroalcohol 5 which was then reduced to the corresponding aminoalcohol 6. Submission of 6 to an aminopinacol rearrangement promoted by nitrous acid deamination then afforded aldehyde 8 through a 1,2-aryl shift. The product fenvaleric aldehyde 8 was then converted to the title compound 2 by a modified Jones oxidation.

Process for making α,β-unsaturated carboxylic acids

α, β-Unsaturated acids of the formula STR1 wherein R1 signifies C1 -C5 -alkyl and Ar signifies an aryl group which is optionally substituted by one or more substituents selected from the group consisting of halogen, phenyl, C1 -C5 -alkyl, C1 -C5 -alkoxy, perfluorinated C1 -C5 -alkyl or perfluorinated C1 -C5 -alkoxy can be obtained from new or known compounds of the formula STR2 Compounds I can be converted by asymmetric hydrogenation into corresponding optically active saturated acids.

Development of an immunoassay for the pyrethroid insecticide esfenvalerate

A competitive enzyme-linked immunosorbent assay was developed for the detection of the pyrethroid insecticide esfenvalerate. Two haptens containing amine or propanoic acid groups on the terminal aromatic ring of the fenvalerate molecule were synthesized and coupled to carrier proteins as immunogens. Five antisera were produced and screened against eight different coating antigens. The assay that had the least interference and was the most sensitive for esfenvalerate was optimized and characterized. The I50 for esfenvalerate was 30 ± 6.2 μg/L, and the lower detection limit (LDL) was 3.0 2+ 1.8 μg/L. The assay was very selective. Other pyrethroid analogues and esfenvalerate metabolites tested did not cross-react significantly in this assay. To increase the sensitivity of the overall method, a C18 sorbent-based solid-phase extraction (SPE) was used for water matrix. With this SPE step, the LDL of the overall method for esfenvalerate was 0.1 μg/L in water samples.