75160-24-6

Usage

Uses

Used in Pesticide Formulations:
PINACOL-D12 is used as an intermediate in the synthesis of isotopically labeled Tebuconazole (T013002) for [application reason] as an ergosterol biosynthesis inhibitor present in most pesticide formulations. This helps in the development of more effective and targeted pest control solutions.
Used in Environmental Science:
PINACOL-D12 is used as an environmental contaminant in the context of the Drinking Water Contaminant Candidate List 3 (CCL 3) as per the United States Environmental Protection Agency (EPA). It aids in the identification, monitoring, and management of potential contaminants in drinking water sources.
Used in Food Contamination Studies:
PINACOL-D12 is used as a tool in the study of food contaminants, helping researchers understand the behavior and impact of various contaminants in the food supply chain. This contributes to the development of safer food production and processing methods.
Used in Plant Uptake Studies:
PINACOL-D12 is used in the study of plant uptake mechanisms, particularly in the context of isotopically labeled compounds. This helps researchers gain insights into the absorption and distribution of these compounds within plants, which can be useful for optimizing agricultural practices and understanding the environmental impact of certain chemicals.

Upstream product

• 666-52-4 [⁽²⁾H₆]acetone 

Downstream Products

• 42983-07-3 2,2-dimethylpropanoic acid-d₉ 

Relevant academic research and scientific papers

A hydrogen-bond flip-flop through a bjerrum-type defect

Back and forth: Femtosecond two-dimensional infrared exchange spectroscopy was used to study the dynamics of the reversal of an intramolecular hydrogen bond. The H-bond reversal resembles a flip-flop motion that is facilitated by two concerted disrotatory torsional isomerizations and that occurs on a time scale of about 2 ps. Copyright

Palladium-Catalyzed Remote Diborylative Cyclization of Dienes with Diborons via Chain Walking

A novel method for catalytic remote bismetalation of alkene substrates by the addition of dimetal reagents is accomplished by using chain walking. In the presence of a palladium catalyst, the reaction of various 1,n-dienes and diborons were converted into cyclopentane derivatives with two boryl groups at remote positions via facile regioselective transformation of an unactivated sp3 C-H bond to a C-B bond. Sequential construction of three distant bonds, which is difficult to achieve by any method, was accomplished for the reactions of 1,n-dienes (n ≥ 7).

Solid-phase synthesis for novel nerve agent adducted nonapeptides as biomarkers

An efficient synthesis of d5-VX adducted nonapeptide and d15-GD adducted nonapeptide via solid-phase approach has been developed. The deuterated peptides could be used as the isotope-labeled internal standard for LC-MS/MS detecting the BuChE-OPNA biomarkers. This method also offers an access to the synthesis and detection of other phosphorylated nonapeptides.

Deuterated Benzene Sulfonamide Thiazole Compounds

Deuterated forms of N-{3-[5-(2-Amino-4-pyrimidinyl)-2-(1,1-dimethylethyl)-1,3-thiazol-4-yl]-2-fluorophenyl}-2,6-difluorobenzenesulfonamide and pharmaceutical compositions containing the same.

Solvent-dependent changes in the triazolinedione-alkene ene reaction mechanism

The influence of the solvent on the triazolinedione-alkene ene reaction mechanism has been investigated. Both inter- and intramolecular kinetic isotope effects with tetramethylethylenes and 2,2,2-(trideuterio)methyl-7-methyl-2,6- octadiene-[D3]-1,1,1 provide, for the first time, strong evidence for changes in the mechanism of the reaction on going from non-protic to polar protic solvents. In non-protic polar or apolar solvents, an aziridinium imide that equilibrates to an insignificant extent with an open intermediate (a dipolar or a polarized biradical) is formed irreversibly in the first, rate-determining step of the reaction, which is followed by fast hydrogen abstraction. On the contrary, in polar protic solvents, hydrogen abstraction is rate limiting, allowing the main dipolar intermediate to equilibrate with its open intermediate(s) as well as with the starting reagents.

Development, mechanism, and scope of the palladium-catalyzed enantioselective allene diboration

In the presence of a chiral phosphoramidite ligand, the palladium-catalyzed diboration of allenes can be executed with high enantioselectivity. This reaction provides high levels of selectivity with a range of aromatic and aliphatic allene substrates. Iso

Homogeneous decatungstate-catalyzed photooxygenation of tetrasubstituted alkenes: A deuterium kinetic isotope effect study

The decatungstate W10O324- homogeneous photocatalyzed oxygenation of tetrasubstituted alkenes has been mechanistically studied. In all cases, allylic hydroperoxides are the major products. The primary inter- and intramolec

Mechanism of the mild functionalization of arenes by diboron reagents catalyzed by iridium complexes. Intermediacy and chemistry of bipyridine-ligated iridium trisboryl complexes

This paper describes mechanistic studies on the functionalization of arenes with the diboron reagent B2pin2 (bis-pinacolato diborane(4)) catalyzed by the combination of 4,4′-di-tert-butylbipyridine (dtbpy) and olefin-ligated iridium halide or olefin-ligated iridium alkoxide complexes. This work identifies the catalyst resting state as [Ir(dtbpy)(COE)(Bpin)3] (COE = cyclooctene, Bpin = 4,4,5,5-tetramethyl-1,3,2-dioxaborolanyl). [Ir(dtbpy)(COE)(Bpin)3] was prepared by independent synthesis in high yield from [Ir(COD)(OMe)] 2, dtbpy, COE, and HBpin. This complex is formed in low yield from [Ir(COD)(OMe)]2, dtbpy, COE, and B2pin2. Kinetic studies show that this complex reacts with arenes after reversible dissociation of COE. An alternative mechanism in which the arene reacts with the Ir(I) complex [Ir(dtbpy)Bpin] after dissociation of COE and reductive elimination of B2pin2 does not occur to a measurable extent. The reaction of [Ir(dtbpy)(COE)(Bpin)3] with arenes and the catalytic reaction of B2pin2 with arenes catalyzed by [Ir(COD)(OMe)]2 and dtbpy occur faster with electron-poor arenes than with electron-rich arenes. However, both the stoichiometric and catalytic reactions also occur faster with the electron-rich heteroarenes thiophene and furan than with arenes, perhaps because η2-heteroarene complexes are more stable than the η2-arene complexes and the η2-heteroarene or arene complexes are intermediates that precede oxidative addition. Kinetic studies on the catalytic reaction show that [Ir(dtbpy)(COE)(Bpin)3] enters the catalytic cycle by dissociation of COE, and a comparison of the kinetic isotope effects of the catalytic and stoichiometric reactions shows that the reactive intermediate [Ir(dtbpy)(Bpin)3] cleaves the arene C-H bond. The barriers for ligand exchange and C-H activation allow an experimental assessment of several conclusions drawn from computational work. Most generally, our results corroborate the conclusion that C-H bond cleavage is turnover-limiting, but the experimental barrier for this bond cleavage is much lower than the calculated barrier.

Mechanism of Thermal Decomposition of Dineopentylbis(triethylphosphine)platinum(II): Formation of Bis(triethylphosphine)-3,3-dimethylplatinacyclobutane

The thermal decomposition of dineopentylbis(triethylphosphine)platinum(II) (1) in cyclohexane solution at 157 deg C yields bis(triethylphosphine)-3,3-dimethylplatinacyclobutane (4) by a reaction which involves dissociation of 1 equiv of triethylphosphine, intramolecular oxidative addition of the C-H bond of a neopentyl methyl group to platinum (3), and reductive elimination of neopentane.Carbon-carbon bond formation resulting in production of dineopentyl is a detectable side-reaction.The overal reaction has Arrenius activation parameters: Ea ca. 49 kcal mol-1, log A ca. 20.The activation energy for phosphine dissociation is 27 - 35 kcal mol-1.Transfer of a hydrogen atom from the triethylphosphine group to aneopentyl moiety occurs at a rate approximately 3percent that of transfer of hydrogen from the methyl of one neopentyl group to the methylene of the other.Any processes which abstract α-methylene hydrogens from the neopentyl group occur at less than 1percent the rate of processes which abstract hydrogens from the neopentyl methyl groups.Substitution of deuterium for hydrogen in either the neopentyl methyl groups or the triethylphosphine groups slows the decomposition reactions (kH/kD ca. 3.0).The mechanism proposed for generation of 4 is based in part on deuterium-labeling experiments: comparison of results by using different labeling patterns for 1 demonstrates the special utility of "inverted" experiments in which hydrogen transfer from a specific site is examined in a system which is otherwise perdeuterated.The driving force for the conversion of 1 to 4 is not obvious: it may be relief of steric strain in 1 , changes in electronic energy due to reorganization of ligands around platinum, or changes in entropy.