5097-99-4

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 72, p. 358, 1950 DOI: 10.1021/ja01157a097

InChI:InChI=1/C12H16N2/c1-3-14(4-2)12(10-13)11-8-6-5-7-9-11/h5-9,12H,3-4H2,1-2H3

Upstream product

• 532-28-5 (RS)-mandelonitrile 
• 109-89-7 diethylamine 
• 4657-12-9 sodium hydroxy(phenyl)methanesulfonate 
• 151-50-8 potassium cyanide 
• 100-52-7 benzaldehyde 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 
• 827-36-1 2-(N,N-dimethylamino)-2-phenylacetonitrile 
• 143-33-9 sodium cyanide 
• 660-68-4 diethyl amine hydrochloride 
• 58046-15-4 O-(Diphenylphosphinoyl)-benzaldehyd-cyanhydrin 
• 7677-24-9 trimethylsilyl cyanide 
• 65459-13-4 bis(diethylamino)cyanoborane 
• 617-84-5 N-formyldiethylamine 
• 100-58-3 phenylmagnesium bromide 

Downstream Products

• 100427-88-1 diethyl-(1,3-diphenyl-propyl)-amine 
• 64857-61-0 diethyl-bibenzyl-α-yl-amine 
• 31788-97-3 N¹,N¹-diethyl-1-phenyl-1,2-ethanediamine 
• 732938-75-9 2-diethylamino-2-phenylacetamide 
• 611-71-2 MANDELIC ACID 
• 109-89-7 diethylamine 
• 64049-87-2 diethyl-(cyano-phenyl-methyl)-methyl-ammonium; iodide 
• 107627-47-4 α-Cyclohexyl-benzyl-diaethylamin 
• 1696-17-9 N,N-diethylbenzamide 
• 85356-10-1 2,5-Bis(diethylamino)-2,5-diphenyladiponitrile 
• 123839-86-1 N-ethyl-N-(phenyl(pyridin-2-yl)methyl)ethanamine 
• 128072-08-2 (1Z,3Z)-N,N,N',N'-Tetraethyl-1,4-diphenyl-buta-1,3-diene-1,4-diamine 
• 495-71-6 phenacylacetophenone 
• 800-13-5 N,N,N',N'-tetraethyl-1,2-diphenylethane-1,2-diamine 

Relevant academic research and scientific papers

One-Pot Synthesis of α-Amino Nitrile Units through Alkylative Strecker Cyanation from Formamides

In this work, we describe the one-pot synthesis of α-amino nitrile units by the concomitant addition of alkyl (or aryl) Grignard reagents and TMS cyanide through alkylative Strecker cyanation from readily available formamides. The reaction is broad in sco

Strecker reactions with hexacyanoferrates as non-toxic cyanide sources

The Strecker reaction is the most widely applied three-component reaction. Although highly useful for the preparation of α-amino nitriles, α-amino acids, hydantoins and numerous related compounds, the need for the application of toxic sources of HCN limits its application in both academic and industrial settings. Here, we present a facile protocol for Strecker reactions using a mixture of potassium ferri- and ferrocyanides as a non-toxic substitute.

Synthesis of α-amino nitriles through Strecker-type reaction using SO3H -functionalized ionic liquid as a homogeneous and water tolerant-acidic catalyst

Task-specific ionic liquid (TSIL) bearing a sulfonic acid group in imidazolium cation (10 mol %), was found to be an effective catalyst for a Strecker-type reaction in water at room temperature. A wide variety of aldehydes/ketones, amines and TMSCN as cya

One-pot three-component synthesis of α-amino nitriles catalyzed by nano powder TiO2 P 25

A simple and efficient method has been developed for the synthesis of α-amino nitriles from aldehydes, amines and trimethylsilyl cyanide (Me3SiCN) in the presence of a catalytic amount of cyanuric acid at room temperature.

Oxalic acid as a simple and efficient organocatalyst for three-component synthesis of α-amino nitriles

A simple, efficient, and general method has been developed for the synthesis of α-amino nitriles. Oxalic acid as a Br?nsted acid promotes the addition of TMSCN to various imines (generated in situ).

Trifluoroethanol as a metal-free, homogeneous and recyclable medium for the efficient one-pot synthesis of α-amino nitriles and α-amino phosphonates

Trifluoroethanol is found to be an efficient and recyclable medium in promoting one-pot, three-component coupling reactions of aldehydes or ketones, amines and trimethylsilyl cyanide or trimethyl phosphite to afford the corresponding α-amino nitriles or α-amino phosphonates in high yields. This protocol does not require the use of an acid or base catalyst.

Superparamagnetic iron oxide as an efficient catalyst for the one-pot, solvent-free synthesis of α-aminonitriles

Superparamagnetic Fe3O4 is shown to act as a very efficient catalyst for the one-pot, three-component synthesis of α-aminonitriles from aldehydes, amines, and TMSCN. The catalyst is easily recovered by the use of an external magnet and reused in several reactions without any noticeable loss of activity. The products are obtained rapidly at room temperature in good purity upon separation of the catalyst and evaporation of the volatiles of the reaction mixture.

Sulfamic acid: an efficient, cost-effective and recyclable solid acid catalyst for the three-component synthesis of α-amino nitriles

α-Amino nitriles are synthesized by the three-component coupling reaction of aldehydes, amines and trimethylsilyl cyanide using sulfamic acid as a heterogeneous solid acid catalyst, under solvent-free conditions in excellent yields. The catalyst was recov

One-pot, solvent-free synthesis of α-aminonitriles under catalysis by magnesium bromide ethyl etherate

A three-component, efficient, and facile procedure has been developed for the synthesis of α-aminonitriles from aldehydes, amines, and trimethylsilyl cyanide using a catalytic amount of magnesium bromide ethyl etherate in the absence of solvent. Rapid formation of products is observed at room temperature in a one-pot procedure under very mild conditions giving excellent yields of the title compounds.

Aminoalkylation with aldehydes mediated by solid lithium perchlorate

The solid LiClO4-mediated one-pot reaction of aldehydes with secondary amines and C nucleophiles afforded the corresponding aminoalkylation products in high yields. Unlike the previous reported procedure, the aminoalkylation of aldehyde was achieved in the presence of only 0.5 equivalents of solid lithium perchlorate in dichloromethane as the solvent with good to high yields at room temperature. Springer-Verlag 2003.