138858-22-7

Basic information

• Product Name: Glycine, N-(phenylmethyl)-N-[(trimethylsilyl)methyl]-, ethyl ester
• CAS NO: 138858-22-7
• Molecular Formula: C15H25NO2Si
• Molecular Weight: 279.454
• Mol File: 138858-22-7.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: Glycine, N-(phenylmethyl)-N-[(trimethylsilyl)methyl]-, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Glycine, N-(phenylmethyl)-N-[(trimethylsilyl)methyl]-, ethyl ester(138858-22-7)
• EPA Substance Registry System: Glycine, N-(phenylmethyl)-N-[(trimethylsilyl)methyl]-, ethyl ester(138858-22-7)

Safety Data

• Hazardous Substances Data: 138858-22-7(Hazardous Substances Data)

Upstream product

• 53215-95-5 N-(trimethylsilylmethyl)benzylamine 
• 105-36-2 ethyl bromoacetate 
• 100-46-9 benzylamine 

Downstream Products

• 6436-90-4 ethyl 2-(benzylamino)acetate 
• 138858-29-4 C₂₄H₂₁NO₄ 
• 138858-23-8 2-hydroxy-2-<methyl>acenaphthylen-1-one 
• 138858-24-9 2-hydroxy-2-<amino>carbethoxymethyl>acenaphthylen-1-one 
• 1619229-71-8 C₇₂H₁₇NO₂ 
• 1619229-77-4 C₇₅H₂₃NO₂Si 

Relevant articles and documents

Photoaddition reactions of azomethine ylides generated from α-aminonitriles to fullerene C60: Formation of fulleropyrrolidines and reaction efficiencies changes depending on reaction conditions

Photoaddition reactions of C60 with both (trimethylsilyl)methyl and either benzyl or phenethyl group containing α-aminonitriles were carried out to explore how product distributions and reaction efficiencies can be influenced by reaction solvent systems. The results show that photoreactions produce both trimethylsilyl- and cyano group containing fulleropyrrolidines as a major (or exclusive) product. Especially, photoreactions performed in either EtOH containing solution or oxygenated environment take place with a much more efficient manner.

Control of Chemoselectivity of SET-Promoted Photoaddition Reactions of Fullerene C60with α-Trimethylsilyl Group-Containing N-Alkylglycinates Yielding Aminomethyl-1,2-dihydrofullerenes or Fulleropyrrolidines

Knowledge about factors that govern chemoselectivity is pivotal to the design of reactions that are utilized to produce complex organic substances. In the current study, single-electron transfer (SET)-promoted photoaddition reactions of fullerene C60 with both trimethylsilyl and various alkyl group-containing glycinates and ethyl N-alkyl-N-((trimethylsilyl)methyl)glycinates were explored to evaluate how the nature of N-alkyl substituents of glycinate substrates and reaction conditions govern the chemoselectivity of reaction pathways followed. The results showed that photoreactions of C60 with glycinates, performed in deoxygenated conditions, produced aminomethyl-1,2-dihydrofullerenes efficiently through a pathway involving the addition of α-amino radical intermediates that are generated by sequential SET-solvent-assisted desilylation of glycinate substrates to C60. Under oxygenated conditions, photoreactions of glycinate substrates, except N-benzyl-substituted analogues, did not take place efficiently owing to quenching of 3C60? by oxygen. Interestingly, N-benzyl-substituted glycinates did react under these conditions to form fulleropyrrolidines through a pathway involving 1,3-dipolar cycloaddition of in situ formed azomethine ylides to C60. The ylide intermediates were formed by regioselective H-atom transfer from glycinates by singlet oxygen. Furthermore, methylene blue (MB)-photosensitized reactions of C60 with glycinates under oxygenated conditions took place efficiently to produce fulleropyrrolidines independent of the nature of N-alkyl substituents of glycinates.

Catalyst free, visible-light promoted photoaddition reactions between C60 and N-trimethylsilylmethyl-substituted tertiary amines for synthesis of aminomethyl-1,2-dihydrofullerenes

An efficient and benign method for the preparation of aminomethyl-substituted fullerenes has been developed. The process, involving catalyst free, visible-light irradiation of 10% EtOH-toluene solutions containing fullerene C60 and N-trimethyls