87813-07-8

Basic information

• Product Name: N-benzyl-N-(trimethylsilylmethyl)aminoacetonitrile
• Synonyms: N-benzyl-N-(trimethylsilylmethyl)aminoacetonitrile;[Benzyl(trimethylsilylmethyl)amino]acetonitrile
• CAS NO: 87813-07-8
• Molecular Formula: C₁₃H₂₀N₂Si
• Molecular Weight: 232.4
• Mol File: 87813-07-8.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• Density: 0.942 g/mL at 25 °C(lit.)
• CAS DataBase Reference: N-benzyl-N-(trimethylsilylmethyl)aminoacetonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: N-benzyl-N-(trimethylsilylmethyl)aminoacetonitrile(87813-07-8)
• EPA Substance Registry System: N-benzyl-N-(trimethylsilylmethyl)aminoacetonitrile(87813-07-8)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-37/39
• Hazardous Substances Data: 87813-07-8(Hazardous Substances Data)

Upstream product

• 50-00-0 formaldehyd 
• 53215-95-5 N-(trimethylsilylmethyl)benzylamine 
• 151-50-8 potassium cyanide 
• 5532-86-5 benzyl cyanoformate 
• 93102-05-7 N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine 
• 100-46-9 benzylamine 
• 624-75-9 iodoacetonitrile 
• 590-17-0 cyanomethyl bromide 

Downstream Products

• 80896-43-1 trans-4-phenyl-1-(phenylmethyl)-3-pyrrolidinecarbonitrile 
• 87813-00-1 2-benzyl-5-phenyl-1,3,3a,6a-tetrahydropyrrolo[3,4-c]pyrrole-4,6-dione 
• 93102-03-5 7-benzyl-3-phenyl-3,7-diazabicyclo<3.3.0>octane-2,4-dione 
• 87813-04-5 (3R,4S)-3-Benzo[1,3]dioxol-5-yl-1-benzyl-4-nitro-pyrrolidine 
• 95832-84-1 2-benzyl-5,6-dimethyl-2H-isoindole-4,7-dione 
• 124562-89-6 3-phenyl-1-(phenylmethyl)-3-pyrrolidinecarboxylic acid methyl ester 
• 87813-03-4 (3SR,4SR)methyl 1-benzyl-4-phenylpyrrolidine-3-carboxylate 
• 73627-97-1 3-hydroxy-3-phenylpropanenitrile 
• 104143-95-5 3-benzyl-5-phenyl-1,3-oxazolidine 
• 87813-06-7 dimethyl 1-benzylpyrrolidine-3,4-dicarboxylate 
• 97998-43-1 1-cyano-amino>-5-hexene 
• 101046-34-8 1-benzyl-2,5-dihydropyrrole-3-carboxylic acid methyl ester 
• 101046-33-7 dimethyl 1-benzyl-2,5-dihydro-1H-3,4-pyrroledicarboxylate 
• 87813-01-2 trans-3-acetyl-1-benzyl-4-phenylpyrrolidine 

Relevant articles and documents

Photochemical Approach for the Preparation of N-Alkyl/Aryl Substituted Fulleropyrrolidines: Photoaddition Reactions of Silyl Group Containing α-Aminonitriles with Fullerene C60

The photochemical reactions of C60 with N-(trimethylsilyl)methyl substituted and N-alkyl/aryl substituted α-aminonitriles were explored to evaluate the scope and reaction efficiency depending on the structural nature of amine substrates. The re

SET-promoted photoaddition reactions of fullerene C60 with tertiary N-trimethylsilylmethyl substituted α-aminonitriles. Approach to the synthesis of fulleropyrrolidine nitriles

Photoaddition reactions of C60 with tertiary N-arylmethyl-N-trimethylsilylmethyl substituted α-aminonitriles were explored. The results show that these photoreactions produce both trimethylsilyl- and cyano group containing fulleropyrrolidines as major products through pathways involving 1,3-dipolar cycloaddition of azomethine ylide intermediates. The ylides are formed either by SET from α-aminonitriles to the triplet excited state of C60 (in N2-purged solutions) followed by desilylation or deprotonation, or by hydrogen atom abstraction by singlet oxygen (in O2-purged solutions). In contrast, photoreactions of C60 with analogous amines that do not contain trimethylsilyl group form fulleropyrrolidines that contain aryl- and cyano substitutents on the pyrrolidine ring. The efficiencies of these photoaddition reactions are influenced by several factors including reaction condition (N2 or O2-purged), solvent polarity, the electronic and structural nature of α-aminonitriles and additive. The presence of trimethylsilyl group in the α-aminonitrile substrates plays a crucial role in enhancing the efficiencies of the fulleropyrrolidine forming reactions.

Diastereofacial selectivity in azomethine ylide cycloaddition reactions derived from chiral α-cyanoaminosilanes

A series of α-cyanoaminosilanes has been found to act as azomethine ylide equivalents. Treatment of these compounds with silver fluoride in the presence of electron deficient olefins gives substituted pyrrolidines in high yield. The extent ofdiastereoselectivity associated with the 1,3-dipolar cycloaddition of chiral azomethine ylides with several dipolarophiles has been studied. Reasonable levels of such diastereoselectivity have been found when optically active α-cyanoaminosilanes are employed as azomethine ylide equivalents. These compounds can be prepared in multigram quantities by treating the appropriate chiral amine with chlorotrimethylsilane followed by reaction of the resulting secondary amine with formaldehyde in the presence of potassium cyanide. It was found that N-benzyl-N-cyanomethyl-N-trimethylsilylmethylamine undergoes stereospecific cycloaddition with dimethyl fumarate and maleate. The stereospecificity of the reaction is consistent with a concerted cycloaddition reaction.