18527-21-4

Usage

Uses

Used in Pharmaceutical Industry:
(4-Fluorophenylthio)acetonitrile is used as an intermediate in the synthesis of pharmaceuticals for its ability to participate in various chemical reactions and synthetic processes. Its unique structure allows it to be a key component in the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical sector, (4-Fluorophenylthio)acetonitrile is utilized as a precursor in the production of agrochemicals, contributing to the development of effective pesticides and other agricultural chemicals that enhance crop protection and yield.
Used in Chemical Synthesis:
(4-Fluorophenylthio)acetonitrile is used as a building block in chemical synthesis for its versatility in forming a variety of organic compounds. Its presence in synthetic processes allows for the creation of new molecules with specific properties for use in different industries.
Used in Industrial Applications:
Due to its unique chemical properties, (4-Fluorophenylthio)acetonitrile may also find use in certain industrial applications, potentially contributing to the development of new materials or processes that benefit from its specific characteristics.

InChI:InChI=1/C9H9FOS/c1-7(11)6-12-9-4-2-8(10)3-5-9/h2-5H,6H2,1H3

Upstream product

• 371-42-6 4-Fluorothiophenol 
• 107-14-2 chloroacetonitrile 
• 6011-14-9 2-aminoacetonitrile hydrochloride 
• 351-67-7 benzyl-(4-fluorophenyl)-sulfide 
• 590-17-0 cyanomethyl bromide 

Downstream Products

• 32083-66-2 (4-fluoro-benzenesulphonyl)-acetonitrile 
• 432-99-5 2-[(4-fluorophenyl)sulfonyl]-1-phenylethan-1-one 

Relevant academic research and scientific papers

Dealkylative intercepted rearrangement reactions of sulfur ylides

Sulfur ylides are well-known to undergo sigmatropic rearrangement reaction. Herein, we describe a novel reactivity of sulfur ylides, which provides access to the product of a formal functional group metathesis upon dealkylative interception of the rearrangement process. Using a simple iron catalyst and in situ generated diazoalkanes this method provides access to α-mercaptoacetonitrile derivatives.

Iron-catalysed carbene-transfer reactions of diazo acetonitrile

A continuous-flow protocol for the synthesis of diazo acetonitrile was developed. It was further applied in iron-catalysed insertion reactions of diazo acetonitrile into N-H and S-H bonds to yield valuable α-substituted acetonitrile, including gram-scale synthesis.

Nanomolar potency and metabolically stable inhibitors of kidney urea transporter UT-B

Urea transporters, which include UT-B in kidney microvessels, are potential targets for development of drugs with a novel diuretic ('urearetic') mechanism. We recently identified, by high-throughput screening, a triazolothienopyrimidine UT-B inhibitor, 1, that selectively and reversibly inhibited urea transport with IC50 = 25.1 nM and reduced urinary concentration in mice (Yao et al.J. Am. Soc. Nephrol., in press). Here, we analyzed 273 commercially available analogues of 1 to establish a structure-activity series and synthesized a targeted library of 11 analogues to identify potent, metabolically stable UT-B inhibitors. The best compound, {3-[4-(1,1-difluoroethyl)benzenesulfonyl]thieno[2,3-e][1,2,3]triazolo[1,5-a] pyrimidin-5-yl}thiophen-2-ylmethylamine, 3k, had IC50 of 23 and 15 nM for inhibition of urea transport by mouse and human UT-B, respectively, and ～40-fold improved in vitro metabolic stability compared to 1. In mice, 3k accumulated in kidney and urine and reduced maximum urinary concentration. Triazolothienopyrimidines may be useful for therapy of diuretic-refractory edema in heart and liver failure.

Rhodium(I)-catalyzed addition of arylboronic acids to (benzyl-/ arylsulfonyl)acetonitriles: Efficient synthesis of (Z)-β- sulfonylvinylamines and β-Keto sulfones

An efficient rhodium(I)-catalyzed addition of arylboronic acids to (benzyl-/arylsulfonyl)acetonitrile is described. Novel β-sulfonylvinylamine products are formed in a stereoselective fashion (Z-alkene). Upon hydrolysis, useful β-keto sulfones are obtained with a broad scope of aryl and sulfonyl substituents.