164169-42-0

Basic information

• Product Name: Carbamic acid, [(trimethylsilyl)oxy]-, 1,1-dimethylethyl ester (9CI)
• Synonyms: Carbamic acid, [(trimethylsilyl)oxy]-, 1,1-dimethylethyl ester (9CI)
• CAS NO: 164169-42-0
• Molecular Formula: C8H19NO3Si
• Molecular Weight: 205.32686
• Product Categories: N-BOC
• Mol File: 164169-42-0.mol

Chemical Properties

• Appearance: /
• Density: 0.954±0.06 g/cm3(Predicted)
• CAS DataBase Reference: Carbamic acid, [(trimethylsilyl)oxy]-, 1,1-dimethylethyl ester (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, [(trimethylsilyl)oxy]-, 1,1-dimethylethyl ester (9CI)(164169-42-0)
• EPA Substance Registry System: Carbamic acid, [(trimethylsilyl)oxy]-, 1,1-dimethylethyl ester (9CI)(164169-42-0)

Safety Data

• Hazardous Substances Data: 164169-42-0(Hazardous Substances Data)

Upstream product

• 1450-14-2 1,1,1,2,2,2-hexamethyldisilane 
• 36016-38-3 tert-Butyl N-hydroxycarbamate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 22737-36-6 O-Trimethylsilylhydroxylamine 

Relevant articles and documents

Thioglycoluril as a highly efficient, recyclable and novel organocatalyst for N-Boc protection of amines

A simple and efficient protocol for the chemoselective mono-N-Boc protection of various structurally diverse amines with di-tert-butyl dicarbonate using thioglycoluril as the catalyst is described. The catalyst can be readily separated from the reaction products by simple filtration and recovered for reuse. No competitive side reactions, such as formation of isocyanate, urea, oxazolidinone, and N,N-di-Boc derivatives were observed.

Lithium perchlorate-catalyzed Boc protection of amines and amine derivatives

A new mild and chemoselective method for mono-N-protection of amines and amine derivatives as tert-butoxycarbonyl derivatives is reported. The reaction proceeds with lithium perchlorate (20 mol %) and pyrocarbonates, and shows general applicability. The catalytic action of LiClO4 is specific for the activation of Boc2O, thus acid-sensitive functionalities of the starting materials remain unchanged in the protection process. This procedure works well for sterically hindered primary amine as well as electron-deficient primary arylamines, primary and secondary amino alcohols, α-amino acid esters, hydroxylamines, hydrazines and sulfonamides.

New N-hydroxy carbamic acid trialkylsilyl derivatives: preparation and thermal reactions

New N-siloxy- or N-alkoxy-carbamic acid derivatives have been prepared.The crystal structure of N-siloxy-O-tert-butyl carbamate was determined.The thermal behaviour of these compounds was studied in the absence and in the presence of other reaction partners.The reaction products were identified by gas chromatography, gas chromatography-mass spectroscopy, IR spectroscopy and NMR.The experimental results can be explained by the formation of a radical-type transition state (carboxynitrene), detected by mass spectroscopy.Keywords: Silicon; Nitrene; Trimethylsilyl; Mass spectroscopy; Crystal structure