127462-20-8

Basic information

• Product Name: 2-phenyl-2-trimethylsilyloxypropanenitrile
• CAS NO: 127462-20-8
• Molecular Weight: 219.359
• Mol File: 127462-20-8.mol
• Article Data: 113

Chemical Properties

• CAS DataBase Reference: 2-phenyl-2-trimethylsilyloxypropanenitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-phenyl-2-trimethylsilyloxypropanenitrile(127462-20-8)
• EPA Substance Registry System: 2-phenyl-2-trimethylsilyloxypropanenitrile(127462-20-8)

Safety Data

• Hazardous Substances Data: 127462-20-8(Hazardous Substances Data)

Upstream product

• 25438-37-3 phenyl(trimethylsiloxy)acetonitrile 
• 74-88-4 methyl iodide 
• 7677-24-9 trimethylsilyl cyanide 
• 98-85-1 1-Phenylethanol 
• 67-56-1 methanol 
• 100-52-7 benzaldehyde 
• 75-77-4 chloro-trimethyl-silane 
• 98-86-2 acetophenone 
• 18052-85-2 2-naphthyltrimethylsilane 
• 100-46-9 benzylamine 
• 20102-12-9 2-hydroxy-2-phenylpropionitrile 
• 143-33-9 sodium cyanide 
• 80-48-8 methyl p-toluene sulfonate 
• 151-50-8 potassium cyanide 

Downstream Products

• 1383925-60-7 (S)-(-)-5-methyl-5-phenyl-2-(pyrid-2-yl)-1,3-oxazoline 
• 17643-24-2 (S)-1-amino-2-phenylpropan-2-ol 
• 17643-24-2 (R)-1-amino-2-phenylpropan-2-ol 
• 52553-03-4 5-methyl-5-phenyloxazolidin-2-one 
• 7403-91-0 NSC 403402 
• 70565-67-2 1,1-Difluoro-3-phenyl-3-<(trimethylsilyl)oxy>-1-butene 
• 70565-71-8 1,1-Difluoro-3-phenyl-3-methyl-2-butenyl acetate 
• 4361-50-6 2-hydroxy-2-phenyl-propionaldehyde 
• 99563-95-8 4-amino-5-methyl-5-phenyl-2(5H)-furanone 
• 1823-91-2 1-phenylethyl cyanide 
• 29624-91-7 1-cyano-1-phenylethyl acetate 
• 70565-65-0 2-Phenyl-2-<(trimethylsilyl)oxy>propanal 
• 95392-12-4 2-fluoro-2-phenylpropionitrile 
• 2019-68-3 Themisone 

Relevant articles and documents

An immobilized organocatalyst for cyanosilylation and epoxidation

An immobilized organocatalyst has been synthesized by covalently anchoring an N-octyldihydroimidazolium hydroxide fragment onto SiO2 (denoted as 1-OH/SiO2). This catalyst exhibits high catalytic performance for the cyanosilylation of

A direct and efficient synthetic method for nitriles from ketones

Cyclic cyano derivatives 3 were obtained by the reaction of Me3SiCN / ZnI2 with the cyclic ketones 2 which gave the trimethylsilyloxy nitriles 4. They were directly transformed to cyano derivatives 3 (70-80% yield) by the reductive reagent Me3SiCl-NaI in acetonitrile in the presence of H2O.

Addition of trimethylsilyl cyanide to aromatic ketones promoted by organic solutions of lithium salts

Cyanosilylation of aromatic ketones is strongly promoted in organic solutions of specific lithium salts (perchlorate and tetrafluoroborate). Acetonitrile solutions of LiBF4 are safe and efficient media for this reaction.

Enantioselective cyanosilylation of ketones catalyzed by double-activation catalysts with N-oxides

Enantioselective addition of trimethylsilyl cyanide to ketones by a catalytic double-activation method is described. By combinatorially using 2.0 mol% of a chiral salen-titanium complex and 1.0 mol% of an achiral tertiary amine N-oxide, aromatic, aliphati

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Activation of TMSCN by N-heterocyclic carbenes for facile cyanosilylation of carbonyl compounds

N-Heterocyclic carbenes were found to be highly effective organocatalysts in activating TMSCN for facile cyanosilylation of carbonyl compounds. Cyano transfer from TMSCN to aldehydes and ketones proceeds at room temperature in the presence of only 0.01-0.

Hydrosilylation of ketone and imine over poly-N-heterocyclic carbene particles

N-Heterocyclic carbene (NHC)-catalyzed ketone/imine hydrosilylation, silane alcohol condensation and asymmetric ketone hydrosilylation reactions were demonstrated for the first time over solid, main-chain poly-NHC particles. The stable and robust poly-NHC

Application of an Electrochemical Microflow Reactor for Cyanosilylation: Machine Learning-Assisted Exploration of Suitable Reaction Conditions for Semi-Large-Scale Synthesis

Cyanosilylation of carbonyl compounds provides protected cyanohydrins, which can be converted into many kinds of compounds such as amino alcohols, amides, esters, and carboxylic acids. In particular, the use of trimethylsilyl cyanide as the sole carbon source can avoid the need for more toxic inorganic cyanides. In this paper, we describe an electrochemically initiated cyanosilylation of carbonyl compounds and its application to a microflow reactor. Furthermore, to identify suitable reaction conditions, which reflect considerations beyond simply a high yield, we demonstrate machine learning-assisted optimization. Machine learning can be used to adjust the current and flow rate at the same time and identify the conditions needed to achieve the best productivity.

Different acidity and additive effects of zirconium metal-organic frameworks as catalysts for cyanosilylation

The Zr(iv) metal-organic framework with 1,4-benzenedicarboxylate (UiO-66) in different forms was studied as a solid catalyst for carbonyl cyanosilylation. The anhydrous material (UiO-66-A) obtained after calcination has open Lewis-acid sites and acts as a heterogeneous and size selective catalyst for the reaction of aldehydes and trimethylsilylcyanide (TMSCN). Notably, it was found that the as-synthesized hydrous form (UiO-66-H) shows comparable activity to UiO-66-A, so UiO-66 can be used as a catalyst for cyanosilylation with no need of high-temperature activation. With a number of intentionally designed control experiments, we demonstrated that the acetic acid enclosed in UiO-66-H during synthesis serves as a Bronsted acid to promote the reaction, though acetic acid is inactive by itself. The different acidity between UiO-66-H and UiO-66-A was confirmed by using the isomerization of α-pinene oxide as a probe reaction. Both UiO-66-H and UiO-66-A are recyclable without significant degradation in framework integrity and catalytic activity. In addition, it was unexpectedly found that pyridine, which is inactive alone, acts as co-catalyst, rather than a Lewis acid poison, to dramatically accelerate the catalytic reaction over UiO-66-H or UiO-66-A. A synergistic mechanism was suggested, in which the Lewis or Bronsted acid activates the aldehyde substrate while pyridine acts as a Lewis base to activate TMSCN.

Low-valent magnesium(i)-catalyzed cyanosilylation of ketones

The magnesium(i) complex [(XylNacnac)Mg]2 was employed as a highly efficient catalyst for the cyanosilylation of a variety of ketones with trimethylsilyl cyanide under mild conditions. In contrast to the traditional stoichiometric us

A dream combination for catalysis: Highly reactive and recyclable scandium(iii) triflate-catalyzed cyanosilylations of carbonyl compounds in an ionic liquid

The catalytic activity of lanthanide triflates, particularly scandium triflate, increased dramatically in [bmim][SbF6], allowing the cyanosilylation of a variety of aldehydes and ketones with a turnover frequency up to 48000 mol h-1 and a total turnover number of 100000.

Highly efficient cyanosilylation of aldehydes and ketones under microwave, solvent-free, and Lewis acid-free conditions

The addition of TMSCN to aldehydes and ketones under microwave irradiation in the absence of any Lewis or Bronsted acid and solvent yielded the corresponding cyanohydrins in good yields in short reaction times (less than 30 min). Copyright Taylor & Francis Group, LLC.

Nanoceria as a recyclable catalyst/support for the cyanosilylation of ketones and alcohol oxidation in cascade

The cyanosilylation of carbonyl compounds is a fundamental reaction in organic synthesis, to give cyanohydrins. Ketones are particularly reluctant to cyanosilane addition and require the action of a catalyst, and despite many soluble Br?nsted and Lewis ac

Ultrathin Near-Infrared Light Activated Nano-Hotplate Catalyst

A combined photothermal-catalytic system that contains a single active element, without using different entities for separate roles (catalytic vs photothermal), is designed here for efficient catalytic reactions. Herein, ultrathin (sub-6 nm) rectangular-l