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Usage

Uses

Used in Pharmaceutical Synthesis:
(RS)-3-(4-fluorophenyl)-3-hydroxypropionitrile is used as a key building block for the synthesis of various pharmaceuticals, due to its ability to be incorporated into molecules with diverse biological activities.
Used in Agrochemical Production:
In the agrochemical industry, (RS)-3-(4-fluorophenyl)-3-hydroxypropionitrile is used as an intermediate for creating compounds with pesticidal properties, contributing to the development of effective crop protection agents.
Used in Medicinal Chemistry Research:
(RS)-3-(4-fluorophenyl)-3-hydroxypropionitrile serves as a valuable research tool in medicinal chemistry, where it is utilized to explore new molecular structures with potential therapeutic applications.
Used in Drug Discovery:
(RS)-3-(4-fluorophenyl)-3-hydroxypropionitrile is also used in drug discovery processes, where it aids in the design and synthesis of novel pharmaceutical intermediates for the treatment of a wide range of diseases.
Used in the Synthesis of Antimicrobial Agents:
(RS)-3-(4-fluorophenyl)-3-hydroxypropionitrile is employed as a starting material for the development of antibacterial, antifungal, and antiviral agents, highlighting its importance in the fight against infectious diseases.
Overall, (RS)-3-(4-fluorophenyl)-3-hydroxypropionitrile is a multifaceted compound with applications spanning across the pharmaceutical, agrochemical, and chemical research industries, showcasing its significance in the development of new drugs and chemicals for various purposes.

Upstream product

• 624-75-9 iodoacetonitrile 
• 459-57-4 4-fluorobenzaldehyde 
• 75-05-8 acetonitrile 
• 18293-53-3 2-trimethylsilylacetonitrile 
• 590-17-0 cyanomethyl bromide 
• 4640-67-9 3-(4-fluorophenyl)-3-oxopropionitrile 
• 403-29-2 2-bromo-4'-fluoroacetophenone 
• 111873-50-8 dibutyl(cyanomethyl)telluronium chloride 

Downstream Products

• 40620-62-0 3-hydroxy-3-(4-fluorophenyl)propanoic acid 
• 522629-15-8 (R)-3-(4'-fluorophenyl)-3-hydroxypropanenitrile 
• 1044833-25-1 (S)-3-(4'-fluorophenyl)-3-hydroxypropanenitrile 
• 1207280-81-6 ethyl 3-(4-fluorophenyl)-3-hydroxypropanimidoate hydrochloride 
• 1374417-22-7 C₁₂H₁₁FO 
• 1374417-00-1 1-(4-fluorophenyl)-1-hydroxyhex-5-en-3-one 

Relevant academic research and scientific papers

Synthesis of β-hydroxyamides through ruthenium-catalyzed hydration/transfer hydrogenation of β-ketonitriles in water: Scope and limitations

A cascade process for the straightforward one-pot conversion of β-ketonitriles into β-hydroxyamides is presented. The process, that proceeds in water employing the arene-ruthenium(II) complex [RuCl2(η6-p-cymene){P(4-C6H4F)2Cl}] as catalyst in combination with sodium formate, involves the initial hydration of the β-ketonitrile substrates to generate the corresponding β-ketoamide intermediates, which subsequently undergo the transfer hydrogenation (TH) of the carbonyl group. Employing a family of forty different β-ketonitriles, featuring diverse substitution patterns, the scope and limitations of the process have been established.

Iridium-catalyzed efficient reduction of ketones in water with formic acid as a hydride donor at low catalyst loading

A highly efficient and chemoselective transfer hydrogenation of ketones in water has been successfully achieved with our newly developed catalyst. Simple ketones, as well as α- or β-functionalized ketones, are readily reduced. Formic acid is used as a traceless hydride source. At very low catalyst loading (S/C = 10:000 in most cases; S/C = 50:000 or 100:000 in some cases), the iridium catalyst is impressively efficient at reducing ketones in good to excellent yields. The TOF value can be as high as up to 26:000 mol mol-1 h-1. A variety of functional groups are well tolerated, for example, heteroaryl, aryloxy, alkyloxy, halogen, cyano, nitro, ester, especially acidic methylene, phenol and carboxylic acid groups.

Ruthenium-Catalyzed Synthesis of β-Hydroxyamides from β-Ketonitriles in Water

An unprecedented hydration/transfer hydrogenation tandem process for the catalytic conversion of β-ketonitriles into synthetically useful β-hydroxyamides in water has been developed, making use of the ruthenium(II) complex [RuCl2(η6-

Substrate evaluation of rhodococcus erythropolis SET1, a nitrile hydrolysing bacterium, demonstrating dual activity strongly dependent on nitrile sub-structure

Assessment of Rhodococcus erythropolis SET1, a novel nitrile hydrolysing bacterial isolate, has been undertaken with 34 nitriles, 33 chiral and 1 prochiral. These substrates consist primarily of β-hydroxy nitriles with varying alkyl and aryl groups at the β position and containing in several compounds different substituents α to the nitrile. In the case of β-hydroxy nitriles without substitution at the α position, acids were the major products obtained, along with recovered nitrile after biotransformation, as a result of suspected nitrilase activity of the isolate. Unexpectedly, amides were found to be the major hydrolysis product when the β-hydroxy nitriles possessed a vinyl group at this position. To probe this behaviour further, additional related substrates were evaluated containing electron-withdrawing groups at the α position, and amide was also observed upon biotransformation in the presence of SET1. Therefore this novel isolate has also demonstrated NHase activity with nitriles that appears to be substrate-dependent.

Zinc-mediated addition of bromoacetonitrile to carbonyl compounds under solvent-free conditions

Zinc mediated addition reaction of bromoacetonitrile with aryl aldehydes and ketones produces β-hydroxynitriles under solvent-free conditions. The valuable feature of the methodology are solvent-free and catalyst-free conditions and short reaction times (5 min).

Versatile iridicycle catalysts for highly efficient and chemoselective transfer hydrogenation of carbonyl compounds in water

Cyclometalated iridium complexes are shown to be highly efficient and chemoselective catalysts for the transfer hydrogenation of a wide range of carbonyl groups with formic acid in water. Examples include α-substituted ketones (α-ether, α-halo, α-hydroxy, α-amino, α-nitrile or α-ester), α-keto esters, β-keto esters and α,β-unsaturated aldehydes. The reduction was carried out at substrate/catalyst ratios of up to 50000 at pH 4.5 and required no organic solvent. The protocol provides a practical, easy and efficient way for the synthesis of β-functionalised secondary alcohols, such as β-hydroxyethers, β-hydroxyamines and β-hydroxyhalo compounds, which are valuable intermediates in pharmaceutical, fine chemical, perfume and agrochemical synthesis. Water wonder: Iridicycle catalysts are versatile and allow the highly efficient and chemoselective transfer hydrogenation of a variety of carbonyl compounds, including problematic and challenging ones, with formate in neat water (see scheme).

A robust nickel catalyst for cyanomethylation of aldehydes: Activation of acetonitrile under base-free conditions

Nick of time: The nickel cyanomethyl complex 1 catalyzes the room temperature coupling of aldehydes with acetonitrile under base-free conditions. The catalytic system is long-lived and remarkably efficient with high turnover numbers (TONs) and turnover fr

N-Heterocyclic carbene-catalyzed cyanomethylation of aldehydes with TMSAN

N-Heterocyclic carbenes (NHCs) have been served as efficient catalysts for cyanomethylation of carbonyl compounds. In the presence of 5 mol % NHC, various aldehydes and 2,2,2-trifluoroacetophenone reacted with trimethylsilylacetonitrile (TMSAN) to give β-hydroxynitriles in moderate to high yields.

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.

GAMMA SECRETASE MODULATORS

In its many embodiments, the present invention provides a novel class of heterocyclic compounds of the formula: as modulators of gamma secretase, methods of preparing such compounds, pharmaceutical compositions containing one or more such compounds, methods of preparing pharmaceutical formulations comprising one or more such compounds, and methods of treatment, prevention, inhibition, or amelioration of one or more diseases associated with the central nervous system using such compounds or pharmaceutical compositions.