15464-07-0

Usage

Uses

Used in Pharmaceutical Research:
α-(4-cyanophenyl)-α-hydroxyacetonitrile is utilized as a reagent in pharmaceutical research for its unique properties and potential applications. It serves as a key building block in the synthesis of various pharmaceutical drugs and biologically active compounds, contributing to the development of new and innovative treatments.
Used in Organic Synthesis:
In the field of organic synthesis, α-(4-cyanophenyl)-α-hydroxyacetonitrile is employed as a reagent due to its unique structure and properties. It plays a crucial role in the synthesis of complex organic molecules, facilitating the creation of new compounds with potential applications in various industries.
Used in Agrochemical Industry:
α-(4-cyanophenyl)-α-hydroxyacetonitrile is also recognized for its potential use as a precursor in the agrochemical industry. Its unique properties and reactivity make it a valuable component in the development of new agrochemicals, such as pesticides and herbicides, that can improve agricultural productivity and crop protection.
Used in Drug Development:
α-(4-cyanophenyl)-α-hydroxyacetonitrile's potential use in the development of new drugs highlights its importance in the pharmaceutical industry. Its unique structure and reactivity allow for the creation of novel drug candidates that can address unmet medical needs and contribute to advancements in healthcare.

Upstream product

• 7677-24-9 trimethylsilyl cyanide 
• 105-07-7 4-cyanobenzaldehyde 
• 773837-37-9 sodium cyanide 
• 73183-24-1 2-(4-cyanophenyl)-2-(trimethylsilyloxy)acetonitrile 
• 74-90-8 hydrogen cyanide 
• 613-90-1 benzoyl cyanide 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 

Downstream Products

• 876-31-3 4-(cyanomethyl)benzonitrile 
• 52798-36-4 methyl α-(4-cyanophenyl)-α-hydroxyacetate 
• 129803-29-8 4-Cyanocarbonyl-benzonitrile 
• 105-07-7 4-cyanobenzaldehyde 
• 619-65-8 4-cyanobenzoic Acid 
• 1259933-42-0 cyano(4-cyanophenyl)methyl pivalate 

Relevant academic research and scientific papers

Electrogenerated Acid-Catalyzed Reactions of Acetals, Aldehydes, and Ketones with Organosilicon Compounds, Leading to Aldol Reactions, Allylations, Cyanations, and Hydride Additions

Exquisite use of electrogenerated acid (EG acid) in the silicon-mediated acid-catalyzed reactions; e.g., aldol reactions, allylations, cyanations, and hydride additions is described.The aldol reaction of acetals 1 with enol trimethylsilyl ethers 3 and 1,2-bis(trimethylsiloxy)alkenes 4 gives the corresponding adducts 5 and 6, respectively.The reaction proceeds smoothly with EG acid derived from perchlorate salts such as LiClO4, n-Bu4NClO4, and Mg(ClO4)2 in dichloromethane using platinum electrodes.The amount of electricity required to complete the reaction implies a cationic process which is mediated by the trimethylsilyl moiety.This aldol reaction is further developed with unprotected carbonyl compounds 2 with 3, giving the trimethylsilyl ethers of the adducts 7.Further utility of this EG acid as a catalyst for a chain reaction is exemplified by the successful application in the following conversions: (1) The allylation of acetals 1 with allyltrimethylsilane (8) to give 9, (2) the cyanation of acetals 1 and unmasked 2 with trimethylsilyl cyanide (10) to give 11, 12, and 13, and (3) the hydride addition of acetals 1 with triethylsilane (14) to give 15.

SUBSTITUTED PYRIDINES AS INHIBITORS OF DNMT1

The invention is directed to substituted pyridine derivatives. Specifically, the invention is directed to compounds according to Formula (Iar): (Iar) wherein Yar, X1ar, X2ar, R1ar, R2ar, R3ar, R4ar and R5ar are as defined herein; or a pharmaceutically acceptable salt or prodrug thereof. The compounds of the invention are selective inhibitors of DNMT1 and can be useful in the treatment of cancer, pre-cancerous syndromes, beta hemoglobinopathy disorders, sickle cell disease, sickle cell anemia, and beta thalassemia, and diseases associated with DNMT1 inhibition. Accordingly, the invention is further directed to pharmaceutical compositions comprising a compound of the invention. The invention is still further directed to methods of inhibiting DNMT1 activity and treatment of disorders associated therewith using a compound of the invention or a pharmaceutical composition comprising a compound of the invention.

Acceptorless and Base-free Dehydrogenation of Cyanohydrin with (η6-Arene)halide(Bidentate Phosphine)ruthenium(II) Complex

Ruthenium-catalyzed dehydrogenation of cyanohydrins under acceptorless and base-free conditions was demonstrated for the first time in the synthesis of acyl cyanide. As opposed to the thermodynamically preferred elimination of hydrogen cyanide, the dehydrogenation of cyanohydrins could be kinetically controlled with ruthenium (II) bidentate phosphine complexes. The effects of the arene, phosphine ligands and counter anions were investigated in regard to catalytic activity and selectivity. Selective dehydrogenation can occur via β-hydride elimination with the experimentally observed [(alkoxide)Ru] complex. (Figure presented.).

Synthesis of dichlorophenyl-, cyanophenyl-and quinolinyl-substituted α-ethoxyacetic acids and derivatives, via α-hydroxyarylacetic acids

A synthetic approach to novel series of α-ethoxy-α-phenylacetamides and α-ethoxy-α-quinolinylacetamides was developed. Aryl aldehydes were converted to cyanohydrins, which were then hydrolyzed or alcoholyzed. Following ethylation of the α-hydroxy group, p

Metal or ammonium alginates as Lewis base catalysts for the 1,2-addition of silyl nucleophiles to carbonyl compounds

Several metal (Na+, Ca2+) or ammonium (n-Bu 4N+) derivatives of alginic acid, an abundant bio-polymer obtained from the cell walls of brown algae, were synthesized. Their potential to act as organocatalysts to catalyze the 1,2-addition of various silyl derivatives to carbonyl compounds was evaluated for the first time. Ammonium alginate 1h is able to promote the reaction in modest to good isolated yields (up to 98%) affording access to a large range of substrates (β-cyano alcohols or ester, β-substituted methylacrylate or acrylonitrile, and cyanohydrin) by using only 5 mol % of catalyst.

Cyanosilylation of aldehydes and ketones catalyzed by nanocrystalline magnesium oxide

Cyanosilylation of various aldehydes and ketones with TMSCN proceeded smoothly under mild conditions to give the corresponding cyanohydrin trimethylsilyl ethers in the presence of nanocrystalline magnesium oxide. The cyanohydrin trimethylsilyl ethers of aldehydes produced cyanohydrins in good to high yields on treatment with 2 N HCl. 29Si NMR spectral evidence proved that the reaction proceeds through the hypervalent silicate species by coordination to O2-/O- (Lewis basic site) of nanocrystalline magnesium oxide. Copyright Taylor & Francis Group, LLC.

P(RNCH2CH2)N: Efficient catalysts for the cyanosilylation of aldehydes and ketones

The 1,2-addition of trialkylsilylcyanides to aldehydes and ketones produces the corresponding protected cyanohydrins in good to excellent yields when carried out at 0°C to room temperature in the presence of catalytic amounts of the nonionic strong base P(RNCH2CH2)N (R = Me, i-Pr) in THF. These catalysts are easily removed from the product by hydrolysis or column filtration through silica gel.

P(MeNMCH2CH2)3N: An effective catalyst for trimethylsilycyanation of aldehydes and ketones

The title non-ionic phosphazane base promotes the trimethylsilycyanation of alkyl and alkyl aldehydes and ketones in moderate to high yields at room temperature. 29Si-NMR spectral evidence for the intermediacy of a phosphazane phosphorus-silicon adduct is presented.

Reductive Coupling of Benzoyl Cyanide and Carbonyl Compounds by Aqueous Ti(III) Ions. A New Convenient and Selective Access to the Less Stable Mixed Benzoins

The reactive species formed by the Ti(III) ion reduction of benzoyl cyanide (1) adds to the C-atom of carbonyl compounds 2 under simple experimental conditions.The intermediate 1,2-diols 3 are smoothly converted, without isolation, into the less thermodynamically stable mixed benzoins 4, which are not accessible by the classical benzoin condensation.The possible mechanisms involved in the reaction are discussed.

Cyano Group Transfer of Acetone Cyanohydrin to Aldehyde Mediated by Titanium Alkoxide and Aluminum Alkyls

Cyano group transfer reaction of acetone cyanohydrin to various aldehydes in the presence of titanium alkoxide and aluminum alkyls to give the corresponding aldehyde cyanohydrins in high yield is described.