17901-93-8

Usage

Uses

Used in Analytical Chemistry:
BENZALDEHYDE-2,3,4,5,6-D5 is used as an internal standard for the quantification of Benzaldehyde by Gas Chromatography (GC) or Liquid Chromatography (LC) coupled with mass spectrometry. The application reason is that the deuterated compound serves as a stable reference point for accurate measurements and quantification of benzaldehyde in various samples, such as environmental, pharmaceutical, and industrial applications. This helps in determining the concentration of benzaldehyde in the sample and allows for better understanding of its presence and role in different contexts.

InChI:InChI=1/C7H6O/c8-6-7-4-2-1-3-5-7/h1-6H/i1D,2D,3D,4D,5D,6D

Upstream product

• 2037-26-5 ⁽²⁾H₈-toluene 
• 1076-43-3 benzene-d6 
• 68-12-2 N,N-dimethyl-formamide 
• 71258-23-6 benzyl alcohol-d7 
• 98-95-3 nitrobenzene 
• 108-24-7 acetic anhydride 
• 64-19-7 acetic acid 
• 108-88-3 toluene 
• 17942-32-4 L-[2,3,4,2',3',4',5',6']-octadeuteriophenylalanine 
• 637-69-4 4-Methoxystyrene 
• 758640-21-0 N-Benzylaniline 
• 51608-60-7 phenyl N-tosyl imine 
• 1079-02-3 benzoic acid-2,3,4,5,6-d5 

Downstream Products

• 91474-15-6 2-Nitro-1-(5>phenyl)<1-D>propen 
• 71258-23-6 benzyl alcohol-d7 
• 68661-19-8 methyl [2,3,4,5,6 -²H₅]benzoate 
• 911207-05-1 C₁₄⁽²⁾H₁₅N 
• 911207-06-2 C₂₁⁽²⁾H₁₄H₉ON 
• 610299-84-8 C₂₁H₉⁽²⁾H₁₄NS 
• 91474-16-7 5-<(Acetyl)(ethoxycarbonyl)methylenamino>-4,5-dihydro-2,5-dimethyl-4-(5>-phenyl)<4-D>-3-furancarbonsaeure-ethylester 
• 91474-17-8 5--4,5-dihydro-2,5-dimethyl-4-(5>-phenyl)<4-D>-3-furancarbonsaeure-ethylester 
• 1133490-86-4 C₁₇H₁₉⁽²⁾H₆N₂O₃⁽¹⁺⁾ 
• 1133490-87-5 C₂₄H₁₉⁽²⁾H₁₂N₂O₄⁽¹⁺⁾ 
• 612-96-4 2-Phenylquinoline 
• 53566-68-0 2-pentadeuteriophenyl-quinoline 
• 1376827-74-5 bis(2,2,2-trichloroethyl) benzoylphosphoramidate 
• 1376827-75-6 bis(2,2,2-trichloroethyl) benzoylphosphoramidate-d5 

Relevant academic research and scientific papers

Water oxidation intermediates applied to catalysis: Benzyl alcohol oxidation

Four distinct intermediates, RuIV=O2+, Ru IV(OH)3+, RuV=O3+, and Ru V(OO)3+, formed by oxidation of the catalyst [Ru(Mebimpy)(4,4′-((HO)2OPCH2)s

An iron(II)[1,3-bis(2'-pyridylimino)isoindoline] complex as a catalyst for substrate oxidation with H2O2 - Evidence for a transient peroxidodiiron(III) species

The complex [Fe(indH)(solvent)3](ClO4)2 (1) has been isolated from the reaction of equimolar amounts of 1,3-bis(2'-pyridylimino)isoindoline (indH) and Fe(ClO4)2 in acetonitrile and characterized by X-ray crystallography and several spectroscopic techniques. It is a suitable catalyst for the oxidation of thioanisoles and benzyl alcohols with H2O2 as the oxidant. Hammett correlations and kinetic isotope effect experiments support the involvement of an electrophilic metalbased oxidant. A metastable green species (2) is observed when 1 is reacted with H2O2 at -40 °C and has a FeIII(μ-O)(μ-O2)FeIII core on the basis of UV/Vis, electron paramagnetic resonance, resonance Raman, and X-ray absorption spectroscopic data.

Nonheme Diiron Oxygenase Mimic That Generates a Diferric-Peroxo Intermediate Capable of Catalytic Olefin Epoxidation and Alkane Hydroxylation including Cyclohexane

Herein are described substrate oxidations with H2O2 catalyzed by [FeII(IndH)(CH3CN)3](ClO4)2 [IndH = 1,3-bis(2′-pyridylimino)isoindoline], involving a spectroscopically characterized (μ-oxo)(μ-1,2-peroxo)diiron(III) intermediate (2) that is capable of olefin epoxidation and alkane hydroxylation including cyclohexane. Species 2 also converts ketones to lactones with a decay rate dependent on [ketone], suggesting direct nucleophilic attack of the substrate carbonyl group by the peroxo species. In contrast, peroxo decay is unaffected by the addition of olefins or alkanes, but the label from H218O is incorporated into the the epoxide and alcohol products, implicating a high-valent iron-oxo oxidant that derives from O-O bond cleavage of the peroxo intermediate. These results demonstrate an ambiphilic diferric-peroxo intermediate that mimics the range of oxidative reactivities associated with O2-activating nonheme diiron enzymes.

Rh(III)-Catalyzed [4+2] Cyclization of 2-Aryl-1H-benzo[d]imidazoles with Maleimides via C-H Activation

A rhodium-catalyzed formal [4+2]-cyclization of 2-aryl-1H-benzo[d]imidazoles with maleimides through C?H bond activation process is described here. Such an approach enables selectively construct a series of functionalized cis-dihydro-benzimidazo[2,1-a]iso

Rh(III)-Catalyzed C-H Olefination Cascades to Divergently Construct Diverse Polyheterocycles by Tuning Manipulations of Directing Groups

Inspired by the diversity created by nature, organic chemists have been using a divergent strategy to improve the synthetic efficiency of diverse molecules. Transition-metal-catalyzed C-H functionalization has become one of the most straightforward, powerful, and atom-economical methods to construct complex scaffolds. However, C-H activation initiated divergent transformation to prepare diverse molecules is still limited. To address this challenge, we herein developed Rh(III)-catalyzed C-H olefination/annulation reaction cascades to divergently construct diverse polyheterocycles by tuning manipulations of directing groups (DGs). Up to 9 distinct scaffolds were creatively synthesized under simple conditions with good functional group tolerance, chemo-, and regioselectivity. Such a versatile strategy and its extension may encourage researchers to discover more promising manipulations of DGs for transition-metal-catalyzed C-H bond activation, making diverse available targets and materials that would have been previously out of range.

Divergent Construction of Diverse Scaffolds through Catalyst-Controlled C?H Activation Cascades of Quinazolinones and Cyclopropenones

A transition-metal-catalyzed C?H activation cascade strategy to rapidly construct diverse quinazolinone derivatives in a one-pot manner is reported. The catalysts play an important role in the different transformations. Additionally, the procedure is scal

One-Pot Construction of Diverse Products using Versatile Cyclopropenones

Tunable C?H activation cascade reactions between quinazolinones and cyclopropenones have been developed. Notably, cyclopropenones, acting as multi-functional building blocks, could be assembled to construct up to 10 distinct heterocyclic scaffolds in a one-pot manner. (Figure presented.).

Metal- And additive-free C-H oxygenation of alkylarenes by visible-light photoredox catalysis

A metal- and additive-free methodology for the highly selective, photocatalyzed C-H oxygenation of alkylarenes under air to the corresponding carbonyls is presented. The process is catalyzed by an imide-acridinium that forms an extremely strong photooxidant upon visible light irradiation, which is able to activate inert alkylarenes such as toluene. Hence, this is an easy to perform, sustainable and environmentally friendly oxidation that provides valuable carbonyls from abundant, readily available compounds.

Photoredox Catalysis of Aromatic β-Ketoesters for in Situ Production of Transient and Persistent Radicals for Organic Transformation

Radical formation is the initial step for conventional radical chemistry. Reported herein is a unified strategy to generate radicals in situ from aromatic β-ketoesters by using a photocatalyst. Under visible-light irradiation, a small amount of photocatalyst fac-Ir(ppy)3 generates a transient α-carbonyl radical and persistent ketyl radical in situ. In contrast to the well-established approaches, neither stoichiometric external oxidant nor reductant is required for this reaction. The synthetic utility is demonstrated by pinacol coupling of ketyl radicals and benzannulation of α-carbonyl radicals with alkynes to give a series of highly substituted 1-naphthols in good to excellent yields. The readily available photocatalyst, mild reaction conditions, broad substrate scope, and high functional-group tolerance make this reaction a useful synthetic tool.

An alternative pathway for the formation of aromatic aroma compounds derived from L-phenylalanine via phenylpyruvic acid in tea (Camellia sinensis (L.) O. Kuntze) leaves

Aromatic aroma compounds contribute to flavor of tea (Camellia sinensis (L.) O. Kuntze) and they are mostly derived from L-phenylalanine via trans-cinnamic acid or directly from L-phenylalanine. The objective of this study was to investigate whether an alternative pathway derived from L-phenylalanine via phenylpyruvic acid is involved in formation of aroma compounds in tea. Enzyme reaction with phenylpyruvic acid showed that benzaldehyde, benzyl alcohol, and methyl benzoate were derived from phenylpyruvic acid in tea leaves. Feeding experiments using [2H8]L-phenylalanine indicated that phenylpyruvic acid was derived from L-phenylalanine in a reaction catalyzed by aromatic amino acid aminotransferases (AAATs). CsAAAT1 showed higher catalytic efficiency towards L-phenylalanine (p ≤ 0.001) while CsAAAT2 showed higher catalytic efficiency towards L-tyrosine (p ≤ 0.001). Both CsAAATs were localized in the cytoplasm of leaf cells. In conclusion, an alternative pathway for the formation of aromatic aroma compounds derived from L-phenylalanine via phenylpyruvic acid occurred in tea leaves.