93554-99-5

Basic information

• Product Name: 2-trimethylsilyloxy-(4-thiomethylphenyl)acetonitrile
• CAS NO: 93554-99-5
• Molecular Weight: 251.425
• Mol File: 93554-99-5.mol

Chemical Properties

• CAS DataBase Reference: 2-trimethylsilyloxy-(4-thiomethylphenyl)acetonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-trimethylsilyloxy-(4-thiomethylphenyl)acetonitrile(93554-99-5)
• EPA Substance Registry System: 2-trimethylsilyloxy-(4-thiomethylphenyl)acetonitrile(93554-99-5)

Safety Data

• Hazardous Substances Data: 93554-99-5(Hazardous Substances Data)

Upstream product

• 7677-24-9 trimethylsilyl cyanide 
• 3446-89-7 4-(Methylthio)benzaldehyde 

Downstream Products

• 96824-37-2 (R)-(4-Methylsulfanyl-phenyl)-((R)-1-phenyl-ethylamino)-acetonitrile; hydrochloride 
• 96824-38-3 (S)-(4-Methylsulfanyl-phenyl)-((R)-1-phenyl-ethylamino)-acetonitrile; hydrochloride 
• 96824-37-2 (S)-(4-Methylsulfanyl-phenyl)-((S)-1-phenyl-ethylamino)-acetonitrile; hydrochloride 
• 1026610-42-3 2-(3,5-Dimethoxy-phenyl)-1-(4-methylsulfanyl-phenyl)-2-trimethylsilanyloxy-ethanone 
• 1207355-59-6 (S)-(+)-acetoxy-(4-methylsulfanyl-phenyl)-acetonitrile 
• 1184849-44-2 2-({6-[3-chloro-4-(trifluoromethyl)phenyl]pyrimidin-4-yl}amino)-1-[4-(methylsulfanyl)phenyl]ethanol 
• 145412-92-6 2-amino-1-(4-methylsulfanyl-phenyl)-ethanol 
• 167173-31-1 2-hydroxy-2-(4-(methylthio)phenyl)acetonitrile 
• 93554-85-9 Amino-(4-methylsulfanyl-phenyl)-acetonitrile 

Relevant articles and documents

1-Aryl-2-((6-aryl)pyrimidin-4-yl)amino)ethanols as competitive inhibitors of fatty acid amide hydrolase

A series of 1-aryl-2-(((6-aryl)pyrimidin-4-yl)amino)ethanols have been found to be competitive inhibitors of fatty acid amide hydrolase (FAAH). One member of this class, JNJ-40413269, was found to have excellent pharmacokinetic properties, demonstrated robust central target engagement, and was efficacious in a rat model of neuropathic pain.

Hydroxynitrile Lyase Isozymes from Prunus communis: Identification, Characterization and Synthetic Applications

Biocatalysts originating from Badamu (Prunus communis) have been applied to catalyze the asymmetric synthesis of (R)-4-methylsulfanylmandelonitrile, a key building block of thiamphenicol and florfenicol. Here, four hydroxynitrile lyase (HNL) isozymes from Badamu were cloned and heterologously expressed in Pichia pastoris. The biochemical properties and catalytic performances of these isozymes were comprehensively explored to evaluate their efficiency and selectivity in asymmetric synthesis. Among then, PcHNL5 was identified with outstanding activity and enantioselectivity in asymmetric hydrocyanation. Under the optimized mild biphasic reaction conditions, seventeen prochiral aromatic aldehydes were converted to valuable chiral cyanohydrins with good yields (up to 94%) and excellent optical purities (up to >99.9% ee), which provide a facile access to numerous chiral amino alcohols, hypoglycemic agents, angiotension converting enzyme (ACE) inhibitors and β-blockers. This work therefore underlines the importance of discovering the most potent biocatalyst among a group of isozymes for converting unnatural substrates into value-added products. (Figure presented.).

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.

ASYMMETRIC SYNTHESIS OF α-AMINONITRILES

The asymmetric synthesis of α-aminonitriles was carried out by the reaction of α-trimethylsilyloxynitriles with optically active α-methylbenzylamine in methanol.The reactions provided moderate yields and good optical purities.