33836-85-0

Basic information

• Product Name: 4-deuterated benzaldehyde
• Synonyms: 4-deuterated benzaldehyde
• CAS NO: 33836-85-0
• Molecular Weight: 107.116
• Mol File: 33836-85-0.mol

Chemical Properties

• CAS DataBase Reference: 4-deuterated benzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 4-deuterated benzaldehyde(33836-85-0)
• EPA Substance Registry System: 4-deuterated benzaldehyde(33836-85-0)

Safety Data

• Hazardous Substances Data: 33836-85-0(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 4409-83-0 4-deuteriotoluene 
• 77765-18-5 [4-²H]benzyl bromide 
• 106-38-7 para-bromotoluene 
• 1122-91-4 4-bromo-benzaldehyde 
• 10602-01-4 p-bromobenzaldehyde 1,3-dioxolane 
• 4294-57-9 para-methylphenylmagnesium bromide 

Downstream Products

• 99532-30-6 4-deuteriocinnamic acid 
• 99532-31-7 4-deuteriohydrocinnamic acid 
• 90625-42-6 trans-4,4'-dideuterio-stilbene 

Relevant articles and documents

Hydrogen-Bond-Donor Solvents Enable Catalyst-Free (Radio)-Halogenation and Deuteration of Organoborons

A hydrogen bond donor solvent assisted (radio)halogenation and deuteration of organoborons has been developed. The reactions exhibited high functional group tolerance and needed only an ambient atmosphere. Most importantly, compared to literature methods, our conditions are more consistent with the principals of green chemistry (e.g., metal-free, strong oxidant-free, more straightforward conditions).

Copper-catalysed low-temperature water-gas shift reaction for selective deuteration of aryl halides

The introduction of deuterium atoms into organic compounds is of importance for basic chemistry, material sciences, and the development of drugs in the pharmaceutical industry, specifically for identification and quantification of metabolites. Hence, methodologies for the synthesis of selectively labelled compounds continue to be a major area of interest for many scientists. Herein, we present a practical and stable heterogeneous copper catalyst, which permits for dehalogenative deuterationviawater-gas shift reaction at comparably low temperature. This novel approach allows deuteration of diverse (hetero)aryl halides with good functional group tolerance, and no reduction of the aromatic rings or other easily reducible formyl and cyano groups. Multi-gram experiments show the potential of this method in organic synthesis and medicinal chemistry.

Electrocatalytic Deuteration of Halides with D2O as the Deuterium Source over a Copper Nanowire Arrays Cathode

Precise deuterium incorporation with controllable deuterated sites is extremely desirable. Here, a facile and efficient electrocatalytic deuterodehalogenation of halides using D2O as the deuteration reagent and copper nanowire arrays (Cu NWAs) electrochemically formed in situ as the cathode was demonstrated. A cross-coupling of carbon and deuterium free radicals might be involved for this ipso-selective deuteration. This method exhibited excellent chemoselectivity and high compatibility with the easily reducible functional groups (C=C, C≡C, C=O, C=N, C≡N). The C?H to C?D transformations were achieved with high yields and deuterium ratios through a one-pot halogenation–deuterodehalogenation process. Efficient deuteration of less-active bromide substrates, specific deuterium incorporation into top-selling pharmaceuticals, and oxidant-free paired anodic synthesis of high-value chemicals with low energy input highlighted the potential practicality.

A preparing method of deuterated aromatic compounds

The invention belongs to the field of chemical synthesis, particularly a preparing method of deuterated aromatic compounds. The method includes subjecting an aryl halide, as an initial raw material, to a palladium catalyzed carbon-halogen bond reduction r

SPIROCYCLIC HAT INHIBITORS AND METHODS FOR THEIR USE

Compounds having a structure of Formula (IX) or a stereoisomer, tautomer or pharmaceutically acceptable salt thereof, wherein R1, R2a, R2b, R3a, R3b, R4a, R4b, Q1----Q2, R6, R7, A, B, W, x, and y are as defined herein and are provided. Pharmaceutical compositions comprising such compounds and methods for treating various HAT-related conditions or diseases, including cancer, by administration of such compounds are also provided.

Direct Hydroxylation of Benzene to Phenol Using Hydrogen Peroxide Catalyzed by Nickel Complexes Supported by Pyridylalkylamine Ligands

Selective hydroxylation of benzene to phenol has been achieved using H2O2 in the presence of a catalytic amount of the nickel complex [NiII(tepa)]2+ (2) (tepa = tris[2-(pyridin-2-yl)ethyl]amine) at 60°C. The maximum yield of phenol was 21% based on benzene without the formation of quinone or diphenol. In an endurance test of the catalyst, complex 2 showed a turnover number (TON) of 749, which is the highest value reported to date for molecular catalysts in benzene hydroxylation with H2O2. When toluene was employed as a substrate instead of benzene, cresol was obtained as the major product with 90% selectivity. When H218O2 was utilized as the oxidant, 18O-labeled phenol was predominantly obtained. The reaction rate for fully deuterated benzene was nearly identical to that of benzene (kinetic isotope effect = 1.0). On the basis of these results, the reaction mechanism is discussed.

Asymmetric synthesis of (S)-mirtazapine: Unexpected racemization through an aromatic ipso-attack mechanism

An asymmetric synthesis of (S)-mirtazapine has been achieved from the synthesis of the racemate by using (S)-1-methyl-3-phenylpiperazine as the starting material. Unfortunately, significant racemization was encountered in the final step, which involved an electrophilic aromatic ring closure of a alcohol by concentrated sulfuric acid. A significantly higher ee was observed when polyphosphoric acid (PPA) was used instead. A remarkable correlation between the amount of PPA used and the ee of the product was revealed, namely, an increase in the ee upon decreasing the amount of PPA. This trend was paralleled by the formation of an increasing amount of a side-product upon lowering the amount of PPA. The racemization and formation of a side-product can be explained by an ipso-attack mechanism during the electrophilic aromatic ring-closure reaction. This mechanism was supported by a mechanistic study using a deuterium-labeled substrate. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Structural dependence of isotope effects in 1H and 13C nuclear magnetic resonance spectra of the trans-N-benzylideneaniline imino group

Deutrium- and 15N-induced isotope effects on 1H and 13C chemical shifts of the imino moiety of 16 trans-N-benzylideneaniline (tBA) isotopomers were determined and analysed. These effects appear to be a sensitive probe of m

Characteristic Effect of Pyridine on the NIH Shift and Selectivity in the Monooxygenation of Aromatic Compounds Catalyzed by a Nonheme Iron Complex/Hydroquinones/O2 System

The high values of the NIH and Me-NIH shifts were observed in the hydroxylation of aromatic compounds such as toluene and xylenes with O2 by the catalytic system in the title.The pyridine concentration greatly affected not only the NIH shift, but the selectivity to form phenols by hydroxylation of the aromatic ring and to form aldehydes by oxidation of the methyl group.

Organic reactions in liquid crystalline solvents. 8. Deuterion NMR studies of the solubilization of some aromatic ketones in the liquid crystalline phases of 4'-butylbicyclohexyl-4-carbonitrile

The nature of the solubilisation of β-phenyl-4-methoxypropiophenone (1) in the nematic and crystal-B liquid crystalline phases of trans,trans-4'-butyl-(1,1'-bicyclohexyl)-4-carbonitrile (CCH-4) has been investigated by deuteriun nmr spectroscopy.This has