501-82-6Relevant academic research and scientific papers
Mixed metal double salt ionic liquids comprised of [HN222]2[ZnCl4] and AlCl3 provide tunable Lewis acid catalysts related to the ionic environment
Kore, Rajkumar,Kelley, Steven P.,Aduri, Pavankumar,Rogers, Robin D.
, p. 7795 - 7803 (2018)
Two solids of differing Lewis acidities, triethylammonium tetrachlorozincate ([HN222]2[ZnCl4]) and AlCl3, have been combined across 0.1 to 0.9 mole fractions (with respect to [HN222]2[ZnCl4]), and homogeneous solid double salts or mixed metal [HN222]2x[(1 - x)AlCl3 + xZnCl4] double salt ionic liquids (DSILs) were obtained at x = 0.33, 0.4, and 0.5 with varying Lewis acidities. The characterization of the prepared DSILs (melting point, color, homogeneity, 1H, 13C, and 27Al nuclear magnetic resonance spectroscopy (NMR), infrared spectroscopy (IR), single crystal X-ray diffraction (SCXRD), and matrix-assisted laser-desorption ionization time-of-flight (MALDI-TOF) mass spectrometry) suggests that [HN222]2[ZnCl4] transfers Cl- from [ZnCl4]2- to the stronger Lewis acid AlCl3, forming intermediate acidic DSILs with [AlCl4]- and [Al2Cl7]- anions and mixed anionic Zn species. Qualitative Lewis acidity measurements using acetonitrile as an IR-active probe showed that the acidity of the DSILs decreased as the amount of [ZnCl4]2- increased. In a Beckman rearrangement reaction of acetophenone oxime, significant catalytic activity was observed for the DSIL at x = 0.33, where the activity of the DSIL was found to be even higher than [HN222][Al2Cl7], AlCl3, [HN222]2[ZnCl4], or ZnCl2 despite its lower Lewis acidity, apparently due to the synergistic effect of AlCl3 and [ZnCl4]2- as Cl- donors for the formation of catalytically active species. The findings illustrate a DSIL-based approach for modifying the catalytic activity of a known complex without changing its inner coordination sphere.
Concentrating Immiscible Molecules at Solid@MOF Interfacial Nanocavities to Drive an Inert Gas–Liquid Reaction at Ambient Conditions
Sim, Howard Yi Fan,Lee, Hiang Kwee,Han, Xuemei,Koh, Charlynn Sher Lin,Phan-Quang, Gia Chuong,Lay, Chee Leng,Kao, Ya-Chuan,Phang, In Yee,Yeow, Edwin K. L.,Ling, Xing Yi
, p. 17058 - 17062 (2018)
Gas–liquid reactions form the basis of our everyday lives, yet they still suffer poor reaction efficiency and are difficult to monitor in situ, especially at ambient conditions. Now, an inert gas–liquid reaction between aniline and CO2 is drive
Inhibition of O-GlcNAcase by PUGNAc is dependent upon the oxime stereochemistry
Perreira, Melissa,Kim, Eun Ju,Thomas, Craig J.,Hanover, John A.
, p. 837 - 846 (2006)
The potent O-GlcNAcase inhibitor PUGNAc was synthesized and two isomers based on the E and Z stereochemistry of the oxime moiety were separated, defined, and tested for activity. Several lines of evidence were examined in an effort to define the correct s
The silver-mediated annulation of arylcarbamic acids and nitrosoarenes toward phenazines
Chen, Fan,Cheng, Jiang,Qian, Peng-Cheng,Wang, Lu
supporting information, (2021/12/17)
A silver-mediated annulation between arylcarbamic acids and nitrosoarenes was developed, leading to phenazines in moderate to good yields with complexity and diversity. This procedure proceeded with the sequential ortho[sbnd] C[sbnd]H functionalization of arylcarbamic acids, insertion to nitroso group and decarboxylative annulation.
Electrochemical Reduction of Carbamates and Carbamic Acids: Implications for Combined Carbon Capture and Electrochemical CO2 Recycling
Bhattacharya, Moumita,Saouma, Caroline T.,Sebghati, Sepehr,Vercella, Yvensha Madeika
, (2020/05/22)
Electrocatalytic reduction of CO2 to CO could represent the first step in solar-driven recycling of CO2 to fuels. While many reports focus on catalyst design or modification of additives such as Lewis or Bronsted acids, there is little focus on modification of the substrate, CO2 itself. Current carbon capture technology employs amines to capture CO2 as carbamates, suggesting that they may serve as a CO2 surrogate, streamlining carbon capture and recycling. Towards this, herein we explore the cyclic voltammetry of seven amines in the presence/absence of CO2. We show that on a glassy carbon electrode in acetonitrile (MeCN) up to -2.7 V vs Fc/Fc+ in tetrabutylammonium hexafluorophosphate (TBAPF6) electrolyte, the amines can only be reduced in the presence of CO2. The potential of the reduction is dependent on the amine identity as well as the protonation state of the resulting species, carbamate versus carbamic acid. Bulk electrolysis experiments indicate little or no reduction to CO and low Faradaic efficiency for formate. This suggests that these amines may be of use in subsequent studies with molecular electrocatalysts that take CO2 to CO and not formate.
A mild copper catalyzed method for the selective deprotection of aryl allyl ethers
Hemming, David S.,Talbot, Eric P.,Steel, Patrick G.
, p. 17 - 20 (2016/12/23)
Copper boryl reagents enable the selective cleavage of aryl allyl ethers to the corresponding phenols in good to moderate yields.
A high-yielding, expeditious, and multicomponent synthesis of urea and carbamate derivatives by using triphenylphosphine/trichloroisocyanuric acid system
Ghodsinia, Sara S.E.,Akhlaghinia, Batool
, p. 104 - 110 (2016/01/25)
An efficient method for the synthesis of urea and carbamate derivatives from amines and alcohols is described by using triphenylphosphine (PPh3)/trichloroisocyanuric acid system. The protocol allows for the preparation of symmetrical, unsymmetrical di, tri-, and tetra-substituted ureas and carbamates and is tolerant of a wide range of functional groups. To optimize the reaction conditions, experimental variables including temperature, the concentration of amine and alcohol, solvent, and reaction time were studied. Satisfactory yields were obtained at the optimized conditions. The present methodology is experimentally simple, mild, and represents a valuable alternative to the existing methods.
Parallel synthesis of ureas and carbamates from amines and CO2 under mild conditions
Peterson, Scott L.,Stucka, Sabrina M.,Dinsmore, Christopher J.
supporting information; experimental part, p. 1340 - 1343 (2010/06/15)
"Chemical Equation Presented" A mild and efficient library synthesis technique has been developed for the synthesis of ureas and carbamates from carbamic acids derived from the DBU-catalyzed reaction of amines and gaseous carbon dioxide. Carbamic acids derived from primary amines reacted with Mitsunobu reagents to generate isocyanates in situ which were condensed with primary and secondary amines to afford the desired ureas. Similarly, carbamic acids from secondary amines reacted with alcohols activated with Mitsunobu reagents to form carbamates.
Mild and convenient synthesis of organic carbamates from amines and carbon dioxide using tetraethylammonium superoxide
Singh, Krishna Nand
, p. 2651 - 2654 (2008/02/12)
A safe and simple method of preparing organic carbamates has been achieved from amines and carbon dioxide using tetraethylammonium superoxide generated in situ. Copyright Taylor & Francis Group, LLC.
Asymmetric dioxazine compounds having a triazinyl bridging group and a method of production and use thereof
-
, (2008/06/13)
An asymmetric dioxazine compound of the following formula in the free acid form, STR1 wherein R is hydrogen, halogen, sulfo or alkoxy, R1, R2 and R3 are each hydrogen or alkyl, X1 and X2 are each hydrogen, halogen, alkyl, alkoxy or phenoxy, Y is alkylene, phenylene or naphthylene, Z is --SO2 CH=CH2, --SO2 CH2 CH2 OSO3 H or the like, V is hydrogen, alkyl, acyl or substituted triazinyl, and Q is halogen, alkoxy, amino or a group similar to that of STR2 provided that R is hydrogen, and Q is amino or a group similar to that of STR3 when V is substituted triazinyl, which is useful for dyeing or printing fiber materials to give dyed or printed products of a brilliant blue color superior in fastness properties, particularly those such as chlorine fastness with superior build-up property.
