90162-44-0

Usage

Uses

Used in Chemical Research:
1-PHENYLETHAN-1,2,2,2-D4-OL is used as an isotopically labeled compound for chemical research purposes. Its deuterated nature allows researchers to study the behavior of 1-phenylethanol in various chemical reactions and processes, providing valuable insights into the underlying mechanisms and properties of the molecule.
Used in Biochemical Studies:
In biochemical studies, 1-PHENYLETHAN-1,2,2,2-D4-OL is used as a stable isotope tracer to investigate the metabolic pathways and enzyme interactions involving 1-phenylethanol. This helps researchers to better understand the biological processes and potential applications of 1-PHENYLETHAN-1,2,2,2-D4-OL in living organisms.
Used in Pharmaceutical Development:
1-PHENYLETHAN-1,2,2,2-D4-OL is used as a research tool in the development of pharmaceuticals. Its deuterated form can be employed to study the pharmacokinetics, pharmacodynamics, and potential therapeutic effects of 1-phenylethanol and its derivatives, aiding in the design and optimization of new drugs.
Used in Analytical Chemistry:
In analytical chemistry, 1-PHENYLETHAN-1,2,2,2-D4-OL serves as an internal standard or a reference compound for the accurate quantification and identification of 1-phenylethanol in complex samples. Its unique isotopic signature allows for improved sensitivity and selectivity in analytical techniques such as mass spectrometry and nuclear magnetic resonance (NMR) spectroscopy.
Used in Environmental Studies:
1-PHENYLETHAN-1,2,2,2-D4-OL can be employed in environmental studies to track the fate and transport of 1-phenylethanol in various ecosystems. Its deuterated form can help researchers to monitor the distribution, degradation, and potential impacts of 1-PHENYLETHAN-1,2,2,2-D4-OL on the environment and its inhabitants.

Upstream product

• 2142-63-4 1-(3-Bromophenyl)ethanone 
• 98-86-2 acetophenone 
• 98-85-1 1-Phenylethanol 
• 99-90-1 para-bromoacetophenone 
• 99-91-2 para-chloroacetophenone 
• 1445-91-6 (S)-1-phenylethanol 

Downstream Products

• 3814-93-5 styrene-α,α,β-d3 
• 17537-31-4 Acetophenone-methyl-d3 
• 1402465-96-6 (4-bromo-2-methyl-2H-pyrazol-3-yl)-carbamic acid 1,2,2,2-tetradeutero-1-phenyl-ethyl ester 
• 1402465-72-8 1-(6-{3-methoxy-4-[1-methyl-5-(1,2,2,2-tetradeutro-1-phenylethoxycarbonylamino)-1H-pyrazol-4-yl]-phenyl}-pyridin-3-yl)-cyclopropanecarboxylic acid hydrochloride 
• 1402466-28-7 1-(6-{3-methoxy-4-[1-methyl-5-(1,2,2,2-tetradeutro-1-phenylethoxycarbonylamino)-1H-pyrazol-4-yl]-phenyl}-pyridin-3-yl)-cyclopropanecarboxylic acid 

Relevant academic research and scientific papers

Stainless-Steel Ball-Milling Method for Hydro-/Deutero-genation using H2O/D2O as a Hydrogen/Deuterium Source

A one-pot continuous-flow method for hydrogen (deuterium) generation and subsequent hydrogenation (deuterogenation) was developed using a stainless-steel (SUS304)-mediated ball-milling approach. SUS304, especially zero-valent Cr and Ni as constituents of the SUS304, and mechanochemical processing played crucial roles in the development of the reactions.

Ruthenium-Catalyzed Deuteration of Alcohols with Deuterium Oxide

The catalytic properties of a series of ruthenium complexes for H/D exchange between D2O and alcohols were studied. The catalytic activity of the ruthenium complexes and the regioselectivity of the H/D exchange reactions were found to be dependent on the auxiliary ligands. While ruthenium η6-cymene complexes such as [(η6-cymene)RuCl(NH2CH2CH2NTs)]Cl, (η6-cymene)RuCl2/NH2CH2CH2OH, and (η6-cymene)Ru{(S,S)-NHCHPhCHPhNTs} catalyzed regioselective deuteration of alcohols with D2O at the β-carbon positions only, octahedral ruthenium complexes such as RuCl2(2-NH2CH2Py)(PPh3)2 (2-NH2CH2Py = 2-aminomethylpyridine) and RuCl2(NH2CH2CH2NH2)(PPh3)2 catalyzed regioselective H/D exchange reactions of D2O with alcohols at both the α- and β-carbon positions of alcohols. The H/D exchange reactions proceed through reversible dehydrogenation of alcohols and hydrogenation of carbonyl compounds involving hydride species and H/D exchange among D2O and carbonyl and hydride species. The different regioselectivities of the H/D exchange reactions can be related to the relative ease of H/D exchange of ruthenium hydride intermediates with D2O. (Chemical Equation Presented).

Hydrogen-transfer reduction of carbonyl compounds promoted by nickel nanoparticles

Nickel(0) nanoparticles, generated from nickel(II) chloride, lithium powder and a catalytic amount of 4,4-di-tert-butylbiphenyl (DTBB) in THF at room temperature, have been found to promote the reduction of a variety of ketones and aldehydes by transfer hydrogenation using isopropanol as the hydrogen donor. The nickel nanoparticles were characterised and could be re-utilised with a good performance in the absence of a base. A mechanistic study demonstrates that the reaction proceeds through a dihydride-type mechanism.

Racemization of secondary alcohols catalyzed by cyclopentadienyl-ruthenium complexes: Evidence for an alkoxide pathway by fast β-hydride elimination-readdition

The racemization of sec-alcohols catalyzed by pentaphenylcyclopentadienyl- ruthenium complex 3 a has been investigated. The mechanism involves ruthenium-alkoxide intermediates: reaction of tert-butoxide ruthenium complex 4 with a series of sec-alcohols with different electronic properties gave ruthenium complexes bearing a secondary alkoxide as a ligand. The characterization of these alkoxide complexes by NMR spectroscopy together with a study of the reaction using in situ IR spectroscopy is consistent with a mechanism in which the alkoxide substitution step and the β-hydride elimination step occur without CO dissociation. The alkoxide substitution reaction is proposed to begin with hydrogen bonding of the incoming alcohol to the active ruthenium-alkoxide intermediate. Subsequent alkoxide exchange can occur via two pathways: i) an associative pathway involving a η3-CpRu intermediate; or ii) a dissociative pathway within the solvent cage. Racemization at room temperature of a 1:1 mixture of (S)-1-phenylethanol and (5)-1-phenyl-[D4]-ethanol gave only rac-1-phenylethanol, and rac-1-phenyl-[D4]-ethanol, providing strong support for a mechanism in which the substrate stays coordinated to the metal center throughout the racemization, and does not leave the coordination sphere. Furthermore, racemization of a sec-alcohol bearing a ketone moiety within the same molecule does not result in any reduction of the original ketone, which rules out a mechanism where the intermediate ketone is trapped within the solvent cage. These results are consistent with a mechanism where η3-Ph5C5-ruthenium intermediates are involved. Competitive racemization on nondeuterated and α-deuterated α-phenylethanols was used to determine the kinetic isotope effect k H/kD for the ruthenium-catalyzed racemization. The kinetic isotope effect kH/kD for p-X-C6H 4CH(OH)CH3 was 1.08, 1.27 and 1.45 for X = OMe, H, and CF3, respectively.

PREPARATION OF DEUTERIATED 1-PHENYLETHANOLS BY REDUCTIVE DEHALOGENATION OF THE CORRESPONDING HALOGENOACETOPHENONES WITH RANEY ALLOYS IN AN ALKALINE DEUTERIUM OXIDE SOLUTION

Deuteriated 1-phenylethanols were prepared by reductive dehalogenation of the corresponding halogenoacetophenones with Raney Ni-Al and Cu-Al alloys in 5percent NaOD-D2O solution.It was found that the Ni-Al alloy introduced greater than expected numbers of deuterium atoms in the phenyl ring, but the expected deuteriated 1-phenylethanols were obtained in high yield and in high isotopic purity when Raney Cu-Al alloy was used.