95392-03-3

Usage

Uses

Used in Organic Synthesis:
(3,4-Dichloro-phenyl)-trimethylsilanyloxy-acetonitrile is used as a reagent for its ability to react with a range of functional groups, facilitating complex organic synthesis processes.
Used in Pharmaceutical and Agrochemical Synthesis:
(3,4-Dichloro-phenyl)-trimethylsilanyloxy-acetonitrile serves as a useful intermediate in the synthesis of pharmaceuticals and agrochemicals due to the unique reactivity provided by the dichloro-phenyl group.
Used in Protecting Alcohols and Phenols:
The trimethylsilyloxy group present in the compound acts as a silyl ether, which is used to protect alcohols and phenols during organic reactions, preventing unwanted side reactions.
Used in Versatile Reactions:
The acetonitrile group within the compound allows for various reactions such as nucleophilic addition and substitution, contributing to its broad application in organic chemistry.
Safety Note:
It is crucial to handle (3,4-Dichloro-phenyl)-trimethylsilanyloxy-acetonitrile with care, as it may pose hazards if not properly managed and stored.

Upstream product

• 177755-45-2 2-(3-fluoro-4-methoxyphenyl)-2-[(trimethylsilyl)oxy]acetonitrile 
• 6287-38-3 3,4-dichlorobenzaldehyde 
• 7677-24-9 trimethylsilyl cyanide 

Downstream Products

• 95392-09-9 2-(3,4-dichlorophenyl)-2-fluoroacetonitrile 
• 177755-55-4 1-(3,4-dichlorophenyl)-2-hydroxy-2-[4-(methylthio)phenyl]ethanone 
• 93534-22-6 1-(3,4-dichlorophenyl)-2-phenyl-ethan-1-one 
• 157672-03-2 1-(4-methylphenyl)-2-[4-(methylthio)phenyl]ethane-1,2,-dione 
• 177755-73-6 2-hydroxy-2-(4-methylthiophenyl)-1-phenylethanone 
• 58022-58-5 1-(4-methylsulfanylphenyl)-2-phenyl-1,2-ethanedione 
• 177754-55-1 4-[4-(methylsulfonyl)phenyl]-5-(2-naphthyl)-2-(trifluoromethyl)-1H-imidazole 
• 177755-60-1 4-[4-(methylthio)phenyl]-5-(2-naphthyl)-2-(trifluoromethyl)-1H-imidazole 
• 177755-57-6 5-(3,4-dichlorophenyl)-4-[4-(methylthio)phenyl]-2-(trifluoromethyl)-1H-imidazole 
• 177755-59-8 2-[4-(methylthio)phenyl]-1-(2-naphthyl)ethane-1,2-dione 
• 177755-58-7 2-hydroxy-2-[4-(methylthio)phenyl]-1-(2-naphthyl)ethanone 
• 177755-56-5 1-(3,4-dichlorophenyl)-2-[4-(methylthio)phenyl]ethane-1,2-dione 
• 95392-15-7 2-(3,4-Dichloro-phenyl)-2-fluoro-ethylamine; hydrochloride 
• 33719-42-5 2-(3,4-dichlorophenyl)-2-hydroxyacetonitrile 

Relevant academic research and scientific papers

Organo-catalyzed Michael addition of 2-fluoro-2-arylacetonitriles

An efficient synthesis of a variety of 2-arylacetonitriles containing a fluorinated stereogenic center through organo-catalyzed Michael addition reaction of 2-fluoro-2-arylacetonitriles has been developed. This protocol uses a cheap organocatalyst (DBU) and has a broad substrate scope: α, β-unsaturated ketones, esters, nitriles and sulfones were all successfully reacted. Importantly, water proved to be a good solvent for this reaction.

Discovery of the First in Vivo Active Inhibitors of the Soluble Epoxide Hydrolase Phosphatase Domain

The emerging pharmacological target soluble epoxide hydrolase (sEH) is a bifunctional enzyme exhibiting two different catalytic activities that are located in two distinct domains. Although the physiological role of the C-terminal hydrolase domain is well-investigated, little is known about its phosphatase activity, located in the N-terminal phosphatase domain of sEH (sEH-P). Herein we report the discovery and optimization of the first inhibitor of human and rat sEH-P that is applicable in vivo. X-ray structure analysis of the sEH phosphatase domain complexed with an inhibitor provides insights in the molecular basis of small-molecule sEH-P inhibition and helps to rationalize the structure-activity relationships. 4-(4-(3,4-Dichlorophenyl)-5-phenyloxazol-2-yl)butanoic acid (22b, SWE101) has an excellent pharmacokinetic and pharmacodynamic profile in rats and enables the investigation of the physiological and pathophysiological role of sEH-P in vivo.

Kinetics and mechanism of the racemic addition of trimethylsilyl cyanide to aldehydes catalysed by Lewis bases

The mechanism by which four Lewis bases, triethylamine, tetrabutylammonium thiocyanate, tetrabutylammonium azide and tetrabutylammonium cyanide, catalyse the addition of trimethylsilyl cyanide to aldehydes is studied by a combination of kinetic and spectr

Investigation of lewis acid versus lewis base catalysis in asymmetric cyanohydrin synthesis

The asymmetric addition of trimethylsilyl cyanide to aldehydes can be catalysed by Lewis acids and/or Lewis bases, which activate the aldehyde and trimethylsilyl cyanide, respectively. It is not always apparent from the structure of the catalyst whether Lewis acid or Lewis base catalysis predominates. To investigate this in the context of using salen complexes of titanium, vanadium and aluminium as catalysts, a Hammett analysis of asymmetric cyanohydrin synthesis was undertaken. When Lewis acid catalysis is dominant, a significantly positive reaction constant is observed, whereas reactions dominated by Lewis base catalysis give much smaller reaction constants. [{Ti(salen)O}2] was found to show the highest degree of Lewis acid catalysis, whereas two [VO(salen)X] (X = EtOSO3 or NCS) complexes both displayed lower degrees of Lewis acid catalysis. In the case of reactions catalysed by [{Al(salen)}2O] and triphenyl- phosphine oxide, a non-linear Ham- mett plot was observed, which is indicative of a change in mechanism with increasing Lewis base catalysis as the carbonyl compound becomes more electron-deficient. These results suggested that the aluminium complex/tri- phenylphosphine oxide catalyst system should also catalyse the asymmetric addition of trimethylsilyl cyanide to ke- tones and this was found to be the case.

Benzenesulfonamide subtituted imidazolyl compounds for the treatment of inflammation

A class of imidazolyl compounds is described for use in treating inflammation and inflammation-related disorders. Compounds of particular interest are defined by Formula II STR1 wherein R1 is selected from lower alkyl, lower haloalkyl, lower hydroxyalkyl, lower aralkenyl, lower aryloxyalkyl, lower arylthioalkyl and heteroaryl; wherein R3 is selected from lower alkyl and amino; and wherein R4 is one or more radicals selected from hydrido, halo, lower alkyl and lower alkoxy; or where R4 together with the phenyl radical forms naphthyl or benzodioxolyl; provided R1 is not lower alkyl when R3 is methyl and when R4 is hydrido, methyl, methoxy or chloro; or a pharmaceutically-acceptable salt thereof.

Enzymatic Preparation of Optically Active Cyanohydrin Acetates

A series of cyanohydrin acetates (1)-(47) of widely varying structures, potential chiral building blocks for numerous synthetic applications, has been prepared in good chemical and often high optical yields by enzymatic hydrolysis of their racemic acetates in the presence of an ester hydrolase from Pseudomonas sp.

A NOVEL SYNTHESIS OF α-FLUOROOACETONITRILES. APPLICATION TO A CONVENIENT PREPARATION OF 2-FLUORO-2-PHENETYLAMINES

α-Fluorophenylacetonitriles (3) are readily prepared by the treatment of the corresponding benzaldehyde cyanohydrin trimethylsilylethers (2) with diethylaminosulfur trifluoride (DAST).This method for the introduction of fluorine alpha to the cyano group is also applicable to the cyanohydrin trimethylsilylethers of aromatic ketones.Diborane reduction of the α-fluorophenylacetonitriles (3) yields 2-fluoro-2-phenethylamines (4).