5941-05-9

Upstream product

• 90-02-8 salicylaldehyde 
• 1068-57-1 acetic acid hydrazide 
• 89-95-2 2-methyl-benzyl alcohol 
• 17604-70-5 2-(((methoxy)imino)methyl)phenylboronic acid 
• 40138-16-7 2-formylbenzene boronic acid 

Downstream Products

• 24257-93-0 2-acetylbenzaldehyde 
• 200732-04-3 Cu⁽²⁺⁾*OC₆H₄CHNNHC(O)CH₃^(1-)*Cl^(1-)*H₂O=Cu(OC₆H₄CHNNHC(O)CH₃)Cl(H₂O) 
• 169620-78-4 Cu⁽²⁺⁾*(C₉H₉O₂N₂)^(1-)*Br^(1-)*H₂O=Cu(C₉H₉O₂N₂)Br(H₂O) 
• 169620-82-0 Cu⁽²⁺⁾*(C₉H₉O₂N₂)^(1-)*CF₃SO₃^(1-)=Cu(C₉H₉O₂N₂)(CF₃SO₃) 

Relevant academic research and scientific papers

A simple sensitive ESIPT on-off fluorescent sensor for selective detection of Al3+ in water

A highly selective and sensitive fluorescent sensor for Al3+ has been developed. The sensor shows great fluorescence turn-on upon binding Al3+ in complete water, giving strong blue emission. In addition, the sensor's turn-on exhibits

Tuning the exchange dynamics of boronic acid hydrazones and oximes with pH and redox control

Dynamic bonds continually form and dissociate at equilibrium. Carbonyl compounds with proximal boronic acids, including 2-formylphenylboronic acid (2-FPBA), have been reported to form highly dynamic covalent hydrazone and oxime bonds in physiological conditions, but strategies to tune the dynamics have not yet been reported. Here, we characterize the dynamics of 2-FPBA-derived hydrazones and oximes and account for both the rapid rate of formation (～102-103M?1s?1) and the relatively fast rate of hydrolysis (～10?4s?1) at physiological pH. We further show that these substrates undergo exchange with α-nucleophiles, which can be reversibly paused and restarted with pH control. Finally, we show that oxidation of the arylboronic acid effectively abolishes the rapid dynamics, which slows the forward reaction by more than 30?000 times and increases the hydrolytic half-life from 50 minutes to 6 months at physiological pH. These results set the stage to explore these linkages in dynamic combinatorial libraries, reversible bioconjugation, and self-healing materials.

Regio- and Stereoselective Synthesis of (Z)-3-Ylidenephthalides via H3PMo12O40-Catalyzed Cyclization of 2-Acylbenzoic Acids with Benzylic Alcohols

We report an exclusively tandem C—O and C—C bond forming beyond the esterification and cyclization reaction of 2-acylbenzoic acids with alcohols to regio- and stereoselective synthesis of the (Z)-3-ylidenephthalides. The reaction uses the nontoxic, inexpensive H3PMo12O40 as catalyst and produces water as the sole by-product, making the reaction environmentally benign and sustainable. Moreover, this reaction features an eco-friendly reaction condition, facile scalability, and easy derivatization of the products to drugs and bioactive compounds. The mechanism studies and density functional theory calculations reveal that the appropriate acid catalyst is the key to the selectivity of this transformation.

Tetrabromomethane as an Organic Catalyst: a Kinetic Study of CBr4-Catalyzed Schiff Condensation

Tetrabromomethane functions as an organic catalyst for non-redox reactions of carbonyl species and, in particular, it enhances the aldehyde–acyl hydrazide condensation to give N-acyl hydrazones. This simple, inexpensive, and commercially available halomet

An efficient CO2 fixation reaction with epoxides catalysed by: In situ formed blue vanadium catalyst from dioxovanadium(+5) complex: Moisture enhanced and atmospheric oxygen retarded catalytic activity

Two new dioxovanadium(+5) complexes, one anionic and other neutral, have been synthesized and characterized by X-ray crystallography in this work. While doing cycloaddition reaction of CO2 to epoxides, taking dioxovanadium(+5) complex as the catalyst, a blue vanadium complex was generated in situ, which was found to be the active catalyst, showing excellent catalytic activity in the presence of tetrabutylammonium bromide as the co-catalyst. The catalytic activity of the catalyst system is enhanced by moisture and, on the other hand, is retarded by atmospheric oxygen. The enhanced catalytic activity at moistened conditions shows the applicability of the catalyst for CO2 fixation from wet flue gas. However, the retarded catalytic activity caused by atmospheric oxygen is important from the mechanistic point of view.

Enantioselective N-Heterocyclic Carbene Catalyzed Synthesis of Functionalized Indenes

An enantioselective NHC (N-heterocyclic carbene) catalyzed synthesis of indenes from bifunctional α,β-unsaturated acyl fluorides and TMS enol ethers has been discovered. The reaction has broad generality (31 examples) and proceeds with high levels of enantioselectivity (most >92:8 er). Mechanistically the reaction likely occurs via a Michael/β-lactonization/decarboxylation sequence. Derivatization studies and limitations are discussed.

Synthesis of 3-hydroxyindanones via potassium salt of amino acid catalyzed regioselective intramolecular aldolization of ortho-diacylbenzenes

First organocatalytic intramolecular aldolization of ortho-diacylbenzenes to construct highly functionalized 3-hydroxyindanones is described. In this transformation a high trans-selectivity is achieved by the use of metal salt of amino acid. This method allows an easy access to the strained spirocyclic 3-hydroxyindanones related to a number of natural product frameworks. Synthesis of a new class of indole skeleton substituted by 3-hydroxyindanones added an extra essence to this new protocol.

Spectro-analytical, X-ray diffraction and computational studies on N′-[(2-hydroxyphenyl)methylidene]acetohydrazide and its copper complex

The structural properties of N′-[(2-hydroxyphenyl)methylidene] acetohydrazide (NHMAH) have been investigated by various spectro-analytical techniques and computational studies. Energies, heat of formation, dipole moment values and Quantitative Structure A

Synthesis, characterization and thermal analysis of a new acetic acid (2-hydroxy-benzylidene)-hydrazide and its complexes with Hg(II) and Pd(II)

The new complexes have been synthesized by the reaction of Hg(II) and Pd(II) with acetic acid(2-hydroxy-benzylidene)- hydrazide (L). These new complexes were characterized by elemental analysis, IR, H NMR spectroscopy and UV spectral techniques. The chang

Phthalides by rhodium-catalyzed ketone hydroacylation

(Chemical Equation Presented) Phthalides are biologically relevant five-membered lactones found in herbs, fruits, and vegetables. Herein we communicate the first atom-economical approach to phthalides by using enantioselective ketone hydroacylation. In the presence of Rh[(Duanphos)]X (X = NO3, OTf, OMs), various 2-ketobenzaldehydes undergo intramolecular hydroacylation to produce phthalide products in good yields and 92-98% ee's. Our study highlights the key role counterions play in controlling both reactivity and enantioselectivity. A concise asymmetric total synthesis of the celery extract (S)-(-)-3-n-butylphthalide is also presented.