1325231-85-3

Basic information

• Product Name: benzhydrylacetamide-d₃
• Synonyms: benzhydrylacetamide-d₃
• CAS NO: 1325231-85-3
• Molecular Weight: 228.266
• Mol File: 1325231-85-3.mol
• Article Data: 15

Chemical Properties

• CAS DataBase Reference: benzhydrylacetamide-d₃(CAS DataBase Reference)
• NIST Chemistry Reference: benzhydrylacetamide-d₃(1325231-85-3)
• EPA Substance Registry System: benzhydrylacetamide-d₃(1325231-85-3)

Safety Data

• Hazardous Substances Data: 1325231-85-3(Hazardous Substances Data)

Upstream product

• 2206-26-0 [D₃]acetonitrile 
• 90-99-3 diphenylchloromethane 
• 776-74-9 Bromodiphenylmethane 

Relevant articles and documents

Switching between Anion-Binding Catalysis and Aminocatalysis with a Rotaxane Dual-Function Catalyst

The "off" state for aminocatalysis by a switchable [2]rotaxane is shown to correspond to an "on" state for anion-binding catalysis. Conversely, the aminocatalysis "on" state of the dual-function rotaxane is inactive in anion-binding catalysis. Switching b

Iodine(III) Derivatives as Halogen Bonding Organocatalysts

Hypervalent iodine(III) derivatives are known as versatile reagents in organic synthesis, but there is only one previous report on their use as Lewis acidic organocatalysts. Herein, we present first strong indications for the crucial role of halogen bonding in this kind of catalyses. To this end, the solvolysis of benzhydryl chloride and the Diels–Alder reaction of cyclopentadiene with methyl vinyl ketone served as benchmark reactions for halide abstraction and the activation of neutral compounds. Iodolium compounds (cyclic diaryl iodonium species) were used as activators or catalysts, and we were able to markedly reduce or completely switch off their activity by sterically blocking one or two of their electrophilic axes. Compared with previously established bidentate cationic halogen bond donors, the monodentate organoiodine derivatives used herein are at least similarly active (in the Diels–Alder reaction) or even decidedly more active (in benzhydryl chloride solvolysis).

Towards redox-switchable organocatalysts based on bidentate halogen bond donors

Redox-active bidentate halogen bond donors based on halopyridinium groups as halogen-bond donating units were synthesized and their structures were elucidated by X-ray diffraction analyses and DFT calculations.Viareversible twofold reduction, these dicationic species can be transformed to neutral compounds which should be much weaker Lewis acids. The corresponding electrochemical data were obtained, and CV as well as UV-vis and NMR techniques were also used to determine binding constants of these halogen bond donors to halides. While all titrations agree on the relative order of binding strengths (with chloride being bound strongest), there are marked deviations in the overall affinity constants which are discussed. In contrast to earlier azo-bridge analogues, the ethylene-linked variants presented herein do not oxidize halides, and thus the novel halogen bond donors could also be used as Lewis acidic organocatalysts in a halide abstraction benchmark reaction, yielding a performance similar to bis(haloimidazolium)-derived catalysts.

Corrigendum to: Digging the Sigma-Hole of Organoantimony Lewis Acids by Oxidation (Angewandte Chemie International Edition, (2018), 57, 42, (13868-13872), 10.1002/anie.201808551)

In Scheme of this Communication, the representation of the hydrogen atoms in the hydrogenation products lacked consistency. The color code used for the hydrogen atoms was also erroneous. A corrected version of Scheme is shown below. None of the conclusion

N-Heterocyclic Iod(az)olium Salts – Potent Halogen-Bond Donors in Organocatalysis

This article describes the application of N-heterocyclic iod(az)olium salts (NHISs) as highly reactive organocatalysts. A variety of mono- and dicationic NHISs are described and utilized as potent XB-donors in halogen-bond catalysis. They were benchmarked in seven diverse test reactions in which the activation of carbon- and metal-chloride bonds as well as carbonyl and nitro groups was achieved. N-methylated dicationic NHISs rendered the highest reactivity in all investigated catalytic applications with reactivities even higher than all previously described monodentate XB-donors based on iodine(I) and (III) and the strong Lewis acid BF3.

Organocatalysis by a multidentate halogen-bond donor: An alternative to hydrogen-bond based catalysis

A charge neutral iodoethynyl-based multidentate halogen-bond donor was synthesized and successfully utilized as an organocatalyst in a benchmark Ritter-type solvolysis reaction. The catalytic activity was monitored using 1H NMR spectroscopy and