83012-15-1

Usage

Uses

Used in Organic Synthesis:
(RS)-2-pyridinecarboxaldehyde cyanohydrin is used as a reagent in the field of organic synthesis for the formation of chiral building blocks. Its unique structure allows for the creation of various complex molecules with specific stereochemistry, which are essential in the development of new pharmaceuticals and agrochemicals.
Used in Pharmaceutical Production:
In the pharmaceutical industry, (RS)-2-pyridinecarboxaldehyde cyanohydrin is utilized as a key intermediate in the synthesis of various drugs. Its ability to form enantiomerically pure compounds is particularly valuable, as it enables the production of single-enantiomer drugs with improved efficacy and reduced side effects.
Used in Agrochemical Production:
Similarly, in the agrochemical industry, (RS)-2-pyridinecarboxaldehyde cyanohydrin serves as an essential building block for the development of new pesticides and other agricultural chemicals. Its chiral properties allow for the creation of more targeted and effective products with minimal environmental impact.
Used in Asymmetric Synthesis:
(RS)-2-pyridinecarboxaldehyde cyanohydrin is also employed in asymmetric synthesis, a technique that involves the selective formation of one enantiomer of a chiral molecule over the other. This is particularly important in the development of enantiomerically pure compounds, which can have significantly different biological activities and properties.

Upstream product

• 1121-60-4 pyridine-2-carbaldehyde 
• 151-50-8 potassium cyanide 
• 74-90-8 hydrogen cyanide 
• 7677-24-9 trimethylsilyl cyanide 
• 773837-37-9 sodium cyanide 

Downstream Products

• 466686-66-8 C₇H₆N₂O 
• 1142908-01-7 C₇H₆N₂O 
• 1207355-62-1 (S)-(-)-acetoxy-(2-pyridyl)-acetonitrile 

Relevant academic research and scientific papers

DEGRADERS AND DEGRONS FOR TARGETED PROTEIN DEGRADATION

Pharmaceutical Degraders and Degrons for use in therapeutic applications are described herein.

Direct crystallographic observation of catalytic reactions inside the pores of a flexible coordination polymer

A new flexible porous coordination polymer (PCP), {[Gd2(L) 3(dmf)4]·4 DMF·3 H2O}n (1), was synthesized under solvothermal condition by reacting [Gd(NO 3)3]·6 H2O with the ligand 2,6,2',6'-tetranitro-biphenyl-4,4'-dicarboxylic acid (H2L). Compound 1 had a 3D coordination polymeric structure with two types of 1D channels (A and B) that were occupied by DMF and water molecules. When crystals of 1 were separately exposed to vapors of various aromatic aldehydes, either the lattice or both the lattice and metal-bound solvent molecules were replaced by aldehyde molecules. The aldehyde molecules inside the pores spontaneously underwent cyanosilylation and Knoevenagel condensation reactions upon exposure to vapors of trimethylsilyl cyanide and malononitrile, respectively. These reactions took place at ambient temperature and pressure. Moreover, both the reactants and the products translocated from one cavity to another. The products that occupied the cavity were expunged upon exposure to the vapors of an aldehyde. Because crystallinity was maintained during these chemical transformations, direct crystallographic observation was possible. Herein, we showed that confinement of the reactants inside the void spaces of the PCP led to the products; we also assessed catalytic activities of this PCP in bulk quantities. Copyright

Chiral solvating agents for cyanohydrins and carboxylic acids

We have shown that a structure as simple as an ion pair of (R)- or (S)-mandelate and dimethylamminopyridinium ions possesses structural features that are sufficient for NMR enantiodiscrimination of cyanohydrins. Moreover, 1H NMR data of cyanohydrins of known configuration obtained in the presence of the mandelate-dimethylaminopyridinium ion pair point to the existence of a correlation between chemical shifts and absolute configuration of cyanohydrins. Mandelate-DMAPH+ ion pair and mandelonitrile form a 1:1 complex with an association constant of 338 M-1 (ΔG 0, -3.4 kcal/mol) for the (R)-mandelonitrile/(R)-mandelate-DMAPH + and 139 M-1 (ΔG0, -2.9 kcal/mol) for the (R)-mandelonitrile/(S)-mandelate-DMAPH+ complex. To understand the origin of enantiodiscrimination, the geometry optimization and energy minimization of the models of ternary complexes of (S)-mandelonitrile/(R)- mandelate/DMAPH+ and (S)-mandelonitrile/(S)-mandelate/DMAPH + complexes was performed using DFT methodology (B3LYP) with the 6-31+G(d) basis set in Gaussian 3.0. Further, analysis of optimized molecular model obtained from theoretical studies suggested that (i) DMAP may be replaced with other amines, (ii) the hydroxyl group of mandelic acid is not necessary for stabilization of ternary complex and may be replaced with other groups such as methyl, (iii) the ion pair should form a stable ternary complex with any hydrogen-bond donor, provided its OH bond is sufficiently polarized, and (iv) α-H of racemic mandelic acid should also get resolved with optically pure mandelonitrile. These inferences were experimentally verified, which not only validated the proposed model but also led to development of a new chiral solvating agent for determination of ee of carboxylic acids and absolute configuration of aryl but not alkyl carboxylic acids.

Enzymatic kinetic resolution of racemic cyanohydrins via enantioselective acylation

Enzymatic kinetic resolution of a series of aromatic and aliphatic cyanohydrins in organic media has been investigated. The behavior of potential lipases, molecular sieves, acyl reagent, reaction temperature, and organic solvents on the kinetic resolution was studied. The influence of substrate structure, steric, and electronic nature and position of the aryl substituent on the enantioselectivity was discussed. Under the optimized reaction conditions, good enantioselectivity could be achieved for most of the investigated compounds. Specifically, substrates 1a, 1c, 1d, 1f, 1u could be resolved with the kinetic enantiomer ratio (E) higher than 200.

A new (R)-hydroxynitrile lyase from Prunus mume: Asymmetric synthesis of cyanohydrins

A new hydroxynitrile lyase (HNL) was isolated from the seed of Japanese apricot (Prunus mume). The enzyme has similar properties with HNL isolated from other Prunus species and is FAD containing enzyme. It accepts a large number of unnatural substrates (benzaldehyde and its variant) for the addition of HCN to produce the corresponding cyanohydrins in excellent optical and chemical yields. A new HPLC based enantioselective assay technique was developed for the enzyme, which promotes the addition of KCN to benzaldehyde in a buffered solution (pH=4.5).

A study of asymmetric hydrocyanation of heteroaryl carboxaldehydes catalyzed by (R)-oxynitrilase under micro-aqueous conditions

A number of new optically active heteroaryl cyanohydrins have been prepared by hydrocyanation under micro-aqueous conditions catalyzed by almond meal (containing (R)-oxynitrilase). Substituent effects on the reaction are discussed. This micro-aqueous meth