3814-93-5

Usage

Uses

Used in Research and Development:
Styrene-alpha,beta,beta-d3 is used as a research compound for the study of chemical reactions and processes. Its isotopic labeling enables researchers to track and analyze specific pathways and mechanisms, providing valuable insights into the behavior of molecules and their interactions.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, styrene-alpha,beta,beta-d3 is used as a tracer compound in the development of new drugs and therapies. Its isotopic labeling allows for the monitoring of drug metabolism and distribution within the body, aiding in the optimization of drug efficacy and safety.
Used in Environmental Science:
Styrene-alpha,beta,beta-d3 is also employed in environmental science as a tracer to study the fate and transport of pollutants in the environment. Its isotopic signature can help researchers understand how contaminants move through ecosystems and how they interact with various environmental factors.
Used in Analytical Chemistry:
In analytical chemistry, styrene-alpha,beta,beta-d3 serves as a reference material for the calibration of instruments and the development of new analytical methods. Its isotopic composition provides a reliable and consistent standard for the accurate measurement of other compounds in complex samples.

Upstream product

• 90162-44-0 [D₄]-rac-5 
• 22293-10-3 (1-diazoethyl)benzene 
• 1235751-69-5 3-trideuteromethyl-3-phenyldiazirine 
• 100-42-5 styrene 
• 811-98-3 d⁽⁴⁾-methanol 
• 75-77-4 chloro-trimethyl-silane 
• 3240-11-7 Phenylacetylene-d1 
• 536-74-3 phenylacetylene 
• 28077-64-7 acetophenone-d5 
• 5123-13-7 5,5-dimethyl-2-phenyl-1,3,2-dioxaborinane 
• 105930-66-3 2,2,2-trideuterio-1-phenyldiazomethane 
• 105930-64-1 diazomethane 
• 105930-65-2 α,α,α-trideuterioacetophenone tosylhydrazone 

Downstream Products

• 1601435-94-2 ethyl 2-methyl-1,5-diphenyl-1D-pyrrole-3-carboxylate 
• 93116-97-3 2,3,3-deuterated-2-phenylpropanoic acid 
• 1438285-25-6 ethyl (E)-5-phenylpent-4-enoate 

Relevant academic research and scientific papers

Heterogeneous Isomerization for Stereoselective Alkyne Hydrogenation to trans-Alkene Mediated by Frustrated Hydrogen Atoms

Stereoselective production of alkenes from the alkyne hydrogenation plays a crucial role in the chemical industry. However, for heterogeneous metal catalysts, the olefins in cis-configuration are usually dominant in the products due to the most important and common Horiuti-Polanyi mechanism involved over the metal surface. In this work, through combined theoretical and experimental investigations, we demonstrate a novel isomerization mechanism mediated by the frustrated hydrogen atoms via the H2 dissociation at the defect on solid surface, which can lead to the switch in selectivity from the cis-configuration to trans-configuration without overhydrogenation. The defective Rh2S3 with exposing facet of (110) exhibits outstanding performance as a heterogeneous metal catalyst for stereoselective production of trans-olefins. With the frustrated hydrogen atoms at spatially separated high-valence Rh sites, the isolated hydrogen mediated cis-to-trans isomerization of olefins can be effectively conducted and the overhydrogenation can be completely inhibited. Furthermore, the bifunctional Rh-S/Pd nanosheets have been synthesized through the surface modification of Pd nanosheets with rhodium and sulfide. With the selective semihydrogenation of alkynes into cis-olefins catalyzed by the small surface PdSx ensembles, the bifunctional Rh-S/Pd nanosheets exhibit excellent activity and stereoselectivity in the one-pot alkyne hydrogenation into trans-olefin, which surpasses the most reported homogeneous and heterogeneous catalysts.

Mechanistic investigation of zinc-promoted silylation of phenylacetylene and chlorosilane: A combined experimental and computational study

The zinc-promoted silylation method is of great importance to synthesize high-performance silicon-containing arylacetylene (PSA) resins in the industry. However, it is difficult to eliminate the accompanied by-product of terminal alkenes due to the lack of mechanistic understanding of the silylation. The initiation of zinc-promoted silylation is facilitated by the interaction between zinc and phenylacetylene. Our DFT calculations indicated that the intermolecular hydrogen transfer of phenylacetylene follows an ionic pathway, which generates a phenylacetylene anion and the corresponding alkene moieties on the zinc surface. The styrene by-product is observed in this stage, with its alkene moieties desorbing as radicals into the solvent under the high reaction temperature. Three possible intermediates of surface phenylacetylene anions were proposed including PhCC-Zn, PhCCZnCl, and (PhCC)2Zn. These carbanion-zinc intermediates undergo an SN2 reaction with Me3SiCl to afford the alkynylsilane on the zinc surface, which is calculated to be the rate-determining step for the zinc-promoted silylation reaction. This journal is

Functionalization of Alkenyl C-H Bonds with D 2 O via Pd(0)/Carboxylic Acid Catalysis

We report herein a simple catalytic method for the extensive labeling of alkenyl C-H bonds through the combination of a palladium(0) complex and a carboxylic acid in the presence of deuterium oxide. The reaction can be applied to a variety of terminal alkenes and the best results are obtained with aryl-substituted examples. This method represents a convenient approach for the preparation of extensively labeled chemicals from the cheapest and safest source of deuterium.

Square Planar Cobalt(II) Hydride versus T-Shaped Cobalt(I): Structural Characterization and Dihydrogen Activation with PNP-Cobalt Pincer Complexes

The carbazole-based pincer ligand R(CbzPNP)H (R = iPr, tBu) has been used for the synthesis and characterization of various low- and high-spin cobalt complexes. Upon treatment of the high-spin complexes R(CbzPNP)CoCl (2R-CoIICl) with NaHBEt3, the selective formation of cobalt(II) hydride 3iPr-CoIIH and T-shaped cobalt(I) complex 4tBu-CoI was observed, depending on the substituents at the phosphorus atoms. For an unambiguous characterization of the reaction products, a density functional theory (DFT) supported paramagnetic NMR analysis was carried out, which established the electron configuration and the oxidation states of the metal atoms, thus demonstrating the significant impact of ligand substitution on the outcome of the reaction. A distinct one-electron reactivity was found for 4tBu-CoI in the dehalogenation of tBuCl and cleavage of PhSSPh. On the other hand, the CoI species displayed two-electron redox behavior in the oxidative addition of dihydrogen. The resulting dihydride complex 6tBu-CoIII(H)2 was found to display sluggish reactivity toward alkenes, whereas the cobalt(II) hydride 3iPr-CoIIH was successfully employed in the catalytic hydrogenation of unhindered alkenes. The stoichiometric hydrogenolysis of 8iPr-CoIIBn at elevated pressure (10 bar) led to a rapid cleavage of the Co-C bond to yield hydride complex 3iPr-CoIIH. On the other hand, treatment of 2iPr-CoIICl with phenethylmagnesium chloride directly resulted in the formation of 3iPr-CoIIH, indicating facile β-H elimination of the alkene insertion product (reversibly) generated in the catalytic hydrogenation. On the basis of these observations, a mechanistic pathway involving a key σ-bond metathesis step of the CoII-alkyl species is proposed.

Mono and dimetallic pyrene-imidazolylidene complexes of iridium(III) for the deuteration of organic substrates and the C-C coupling of alcohols

Three different Ir(iii) complexes with pyrene-containing N-heterocyclic carbenes have been prepared and characterized. Two complexes contain a monodentate pyrene-imidazolylidene ligand, and have the formulae [IrCp?Cl2(pyrene-NHC)] and [IrCp?(CO3)(pyrene-NHC)]. The third complex is a dimetallic complex with a pyrene-di-imidazolylidene bridging ligand, with the formula [{IrCp?(CO3)}2(μ-pyrene-di-NHC)]. The catalytic activity of the three complexes was tested in the H/D exchange of organic substrates, and in the β-alkylation of 1-phenylethanol with primary alcohols. In the deuteration of organic substrates, the carbonate complexes are active even in the absence of additives. The dimetallic complex is the most active one in the catalytic coupling of alcohols, a result that may be interpreted as a consequence of the cooperativity between the two metal centres.

Inorganic clusters with a [Fe2MoOS3] core - A functional model for acetylene reduction by nitrogenases

We report the first example of a wholly inorganic mimic of a part of the FeMoco active centre of nitrogenases. We detail the synthesis, characterisation and reactivity of two related, transient hydride-containing inorganic clusters, a dihydride complex and a vinyl monohydride complex, which bear the [Fe2MoOS3] portion of FeMoco. The dihydride complex is capable of reducing acetylene to ethylene via the vinyl monohydride complex. In the reaction cycle, a transient low-valent complex was generated by the reductive elimination of H2 or ethylene from dihydride or vinyl monohydride complexes, respectively.

Well-Defined Cobalt(I) Dihydrogen Catalyst: Experimental Evidence for a Co(I)/Co(III) Redox Process in Olefin Hydrogenation

The synthesis of a cobalt dihydrogen CoI-(H2) complex prepared from a CoI-(N2) precursor supported by a monoanionic pincer bis(carbene) ligand, MesCCC (MesCCC = bis(mesityl-benzimidazol-2-ylidene)phenyl), is described. This species is capable of H2/D2 scrambling and hydrogenating alkenes at room temperature. Stoichiometric addition of HCl to the CoI-(N2) cleanly affords the CoIII hydridochloride complex, which, upon the addition of Cp2ZrHCl, evolves hydrogen gas and regenerates the CoI-(N2) complex. Furthermore, the catalytic olefin hydrogenation activity of the CoI species was studied by using multinuclear and parahydrogen (p-H2) induced polarization (PHIP) transfer NMR studies to elucidate catalytically relevant intermediates, as well as to establish the role of the CoI-(H2) in the CoI/CoIII redox cycle.

Selective H/D Exchange at Vinyl and Methylidene Groups with D2O Catalyzed by an Iridium Complex

Selective H/D exchange at vinyl and methylidene groups of alkenes with D2O was promoted by an iridium catalyst generated in situ from a hydroxoiridium complex and N-mesylbenzamide.

Heterolytic H2 cleavage and catalytic hydrogenation by an iron metallaboratrane

Reversible, heterolytic addition of H2 across an iron-boron bond in a ferraboratrane with formal hydride transfer to the boron gives iron-borohydrido-hydride complexes. These compounds catalyze the hydrogenation of alkenes and alkynes to the respective alkanes. Notably, the boron is capable of acting as a shuttle for hydride transfer to substrates. The results are interesting in the context of heterolytic substrate addition across metal-boron bonds in metallaboratranes and related systems, as well as metal-ligand bifunctional catalysis.

Mild and selective H/D exchange at the β position of aromatic α-olefins by N-heterocyclic carbene-hydride-rhodium catalysts

Pacman bites selectively! Stable rhodium(III)-N-heterocyclic carbene-hydride complexes (Pacman-like catalysts) are highly active and selective catalysts for H/D exchange at the β position of aromatic α-olefins (see picture). The interplay between bulky N-