1076-07-9

Usage

Uses

Used in Research and Development:
PHENYLACETIC-2,2-D2 ACID is used as a research compound for [application reason] in the field of [application industry]. Its isotopically labeled nature allows for enhanced tracking and analysis in various experimental setups, contributing to a better understanding of the underlying processes and mechanisms.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, PHENYLACETIC-2,2-D2 ACID is used as a key intermediate in the synthesis of various drugs and drug candidates. Its unique properties enable the development of novel therapeutic agents with improved efficacy and reduced side effects.
Used in Chemical Synthesis:
PHENYLACETIC-2,2-D2 ACID is used as a building block in the chemical synthesis of a wide range of compounds, including organic molecules, polymers, and materials with specific properties. Its isotopically labeled nature can be advantageous in tracing the synthesis pathways and understanding the reaction mechanisms.
Used in Analytical Chemistry:
In analytical chemistry, PHENYLACETIC-2,2-D2 ACID is used as a reference material or internal standard for the accurate quantification and identification of target compounds in complex samples. Its distinct isotopic signature allows for improved sensitivity and precision in analytical techniques such as mass spectrometry and nuclear magnetic resonance (NMR) spectroscopy.
Used in Environmental Studies:
PHENYLACETIC-2,2-D2 ACID can be employed in environmental studies as a tracer to investigate the fate and transport of pollutants, contaminants, or nutrients in various ecosystems. Its isotopically labeled nature enables the differentiation between natural and anthropogenic sources, providing valuable insights into the environmental processes and potential risks associated with these substances.
Used in Agricultural Research:
In agricultural research, PHENYLACETIC-2,2-D2 ACID can be utilized as a labeled compound to study the metabolism, uptake, and transport of nutrients in plants. This information can be crucial for the development of more efficient and sustainable agricultural practices, as well as for understanding the interactions between plants and their surrounding environment.
Overall, PHENYLACETIC-2,2-D2 ACID is a versatile and valuable compound with a wide range of applications across various industries, including research and development, pharmaceuticals, chemical synthesis, analytical chemistry, environmental studies, and agricultural research. Its unique properties and isotopically labeled nature make it an indispensable tool in advancing our knowledge and understanding of various scientific and industrial processes.

InChI:InChI=1/C8H8O2/c9-8(10)6-7-4-2-1-3-5-7/h1-5H,6H2,(H,9,10)/i6D2

Upstream product

• 103-82-2 phenylacetic acid 
• 114-70-5 sodium phenylacetate 
• 93-89-0 benzoic acid ethyl ester 
• 93-58-3 benzoic acid methyl ester 
• 159087-45-3 4,4,5,5-tetramethyl-2-phenylethynyl-[1,3,2]dioxaborolane 
• 124-38-9 carbon dioxide 
• 33641-51-9 [(phenylmethyl-d₂)sulfonyl]benzene 
• 140-29-4 phenylacetonitrile 
• 21175-64-4 1,1-dideuteriophenylmethanol 
• 935-66-0 phenylacetonitrile-α,α-d2 
• 51271-29-5 [1',1'-2H₂]benzyl bromide 
• 33712-34-4 benzyl-d2 chloride 

Downstream Products

• 33712-34-4 benzyl-d2 chloride 
• 51271-29-5 [1',1'-2H₂]benzyl bromide 
• 51086-45-4 2,2-dideuterio-2-phenyl-ethanol 
• 107473-33-6 2-phenylethanol 
• 50561-93-8 1-fluoro-2-phenylathane-2,2-d₂ 
• 286967-45-1 1-trimethylsilyloxy-3-(2,2-d₂-phenethyl)-1-cyclohexene 
• 23088-37-1 2,2-d₂-phenethyl bromide 
• 51086-44-3 phenylacetaldehyde-2,2-d₂ 
• 83691-92-3 (2,2-dideuterio-2-phenylethyl)triphenylphosphonium bromide 
• 116503-64-1 C₁₆H₁₄⁽²⁾H₂ 
• 100638-57-1 C₂₈H₂₆⁽²⁾H₄O₆ 
• 100638-58-2 C₂₅H₂₆⁽²⁾H₄O₈ 
• 100638-61-7 C₃₄H₂₈⁽²⁾H₈O₅ 
• 100638-62-8 C₃₆H₃₁⁽²⁾H₈NO₆ 

Relevant academic research and scientific papers

Dual Catalytic Switchable Divergent Synthesis: An Asymmetric Visible-Light Photocatalytic Approach to Fluorine-Containing ?γ-Keto Acid Frameworks

Herein, we describe a novel and efficient method for constructing a series of fluorine-containing ?γ-keto acid derivatives through combining visible-light photoredox catalysis and chiral Lewis acid catalysis. With this dual catalytic strategy, a variety of chiral ?γ-keto amides containing a gem-difluoroalkyl group and a series of fluorine-containing α,β-unsaturated-?γ-keto esters were successfully constructed with high stereoselectivities, respectively. A series of experiments showed that the chemoselectivity of this process was highly dependent on the fluorine reagents besides the Lewis acid catalysts. This approach facilitates rapid access to ?γ-keto acid derivatives, an important class of precursors for pharmaceuticals, plasticizers, and various other additives.

Polarization IR spectra of the hydrogen bond in phenylacetic acid crystals: H/D isotopic effects - Temperature and polarization effects

This paper deals with experimental studies and with quantitative interpretation of the polarized IR crystalline spectra of phenylacetic acid and of its deuterium isotopomers d2 and d7. The spectra were measured in the νO-H

Iron Catalyzed Double Bond Isomerization: Evidence for an FeI/FeIII Catalytic Cycle

Iron-catalyzed isomerization of alkenes is reported using an iron(II) β-diketiminate pre-catalyst. The reaction proceeds with a catalytic amount of a hydride source, such as pinacol borane (HBpin) or ammonia borane (H3N?BH3). Reactivity with both allyl arenes and aliphatic alkenes has been studied. The catalytic mechanism was investigated by a variety of means, including deuteration studies, Density Functional Theory (DFT) and Electron Paramagnetic Resonance (EPR) spectroscopy. The data obtained support a pre-catalyst activation step that gives access to an η2-coordinated alkene FeI complex, followed by oxidative addition of the alkene to give an FeIII intermediate, which then undergoes reductive elimination to allow release of the isomerization product.

Aerobic Oxidative Dehydrogenation of Ketones to 1,4-Enediones

An efficient and unprecedented strategy for the synthesis of 1,4-enediones from saturated ketones has been developed via palladium-catalyzed oxidative dehydrogenation. The protocol employs molecular oxygen as the sole oxidant and represents an atom- and step-economic process. The approach showed broad substrate scope, good functional group tolerance, and complete E-stereoselectivity. The reaction mechanism has been investigated through deuterium-labeling experiments and intermediate experiments.

Desulfonylative Electrocarboxylation with Carbon Dioxide

Electrocarboxylation of organic halides is one of the most investigated electrochemical approaches for converting thermodynamically inert carbon dioxide (CO2) into value-added carboxylic acids. By converting organic halides into their sulfone derivatives, we have developed a highly efficient electrochemical desulfonylative carboxylation protocol. Such a strategy takes advantage of CO2as the abundant C1 building block for the facile preparation of multifunctionalized carboxylic acids, including the nonsteroidal anti-inflammatory drug ibuprofen, under mild reaction conditions.

Oxidation of Alkynyl Boronates to Carboxylic Acids, Esters, and Amides

A general efficient protocol was developed for the synthesis of carboxylic acids, esters, and amides through oxidation of alkynyl boronates, generated directly from terminal alkynes. This protocol represents the first example of C(sp)?B bond oxidation. This approach displays a broad substrate scope, including aryl and alkyl alkynes, and exhibits excellent functional group tolerance. Water, primary and secondary alcohols, and amines are suitable nucleophiles for this transformation. Notably, amino acids and peptides can be used as nucleophiles, providing an efficient method for the synthesis and modification of peptides. The practicability of this methodology was further highlighted by the preparation of pharmaceutical molecules.

Nickel-Catalyzed Electrochemical Reductive Relay Cross-Coupling of Alkyl Halides to Aryl Halides

A highly regioselective Ni-catalyzed electrochemical reductive relay cross-coupling between an aryl halide and an alkyl halide has been developed in an undivided cell. Various functional groups are tolerated under these mild reaction conditions, which pro

Enantioselective Copper(I)/Chiral Phosphoric Acid Catalyzed Intramolecular Amination of Allylic and Benzylic C?H Bonds

Radical-involved enantioselective oxidative C?H bond functionalization by a hydrogen-atom transfer (HAT) process has emerged as a promising method for accessing functionally diverse enantioenriched products, while asymmetric C(sp3)?H bond amination remains a formidable challenge. To address this problem, described herein is a dual CuI/chiral phosphoric acid (CPA) catalytic system for radical-involved enantioselective intramolecular C(sp3)?H amination of not only allylic positions but also benzylic positions with broad substrate scope. The use of 4-methoxy-NHPI (NHPI=N-hydroxyphthalimide) as a stable and chemoselective HAT mediator precursor is crucial for the fulfillment of this transformation. Preliminary mechanistic studies indicate that a crucial allylic or benzylic radical intermediate resulting from a HAT process is involved.

Nickel-Catalyzed Allylic C(sp2)–H Activation: Stereoselective Allyl Isomerization and Regiospecific Allyl Arylation of Allylarenes

Stereoselective allyl isomerization and regiospecific allyl arylation reactions of allylarenes with a catalytic system comprising nickel(II) with an aryl Grignard reagent were studied. Both reactions are triggered by allylic internal C(sp2)–H activation by in-situ-formed Ni0, which is inserted into the C–H bond at the 2-position of the allyl moiety without a directing group. The isomerization of allylarene to 1-propenylarene favors the E isomer and proceeds with quantitative conversion. The arylation takes place through oxidative cross-coupling of allylarenes with excess Grignard reagent. It occurs regiospecifically at the position of C(sp2)–H activation and represents a new method for the synthesis of 1,1-disubstituted olefins. The results of deuterium labeling experiments reveal an alkenyl/alkyl mechanism involving allylic internal C(sp2)–H activation and multiple intermolecular 1,2-, 1,3-, and 2,3-hydride shifts. These methods represent new approaches to the functionalization of olefins, and the mechanistic investigations could be helpful for the discovery and design of new strategies for olefin functionalization.

Development of a QuEChERS-Based Stable-Isotope Dilution LC-MS/MS Method to Quantitate Ferulic Acid and Its Main Microbial and Hepatic Metabolites in Milk

Forage plants of the Poaceae family are grown as pasturage or used for the production of hay, straw, corn stover, etc. Although ferulic acid contents of grasses are generally high, the amount of ingested ferulic acid differs depending on the type of forage, resulting in varying contents of ferulic acid and its microbial and hepatic metabolites in milk. Concentrations and patterns of these metabolites may be used as markers to track different forages in livestock feeding. Therefore, we developed a stable isotope dilution assay to quantitate ferulic acid, 12 ferulic acid-based metabolites, p-coumaric acid, and cinnamic acid in milk. Because most analytes were not commercially available as stable isotope labeled standard compounds, they were synthesized as 13C- or deuterium-labeled standard compounds. A modification of the QuEChERS method, a Quick, Easy, Cheap, Effective, Rugged, and Safe approach usually applied to analyze pesticides in plant-based products, was used to extract the phenolic acids from milk. Determination was carried out by LC-ESI-MS/MS in scheduled multiple reaction monitoring modus. By using three different milk samples, the applicability of the validated approach was demonstrated.