93454-85-4

Basic information

• Product Name: Propanoic acid, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-methyl-, methyl ester, (S)-
• CAS NO: 93454-85-4
• Molecular Formula: C11H24O3Si
• Molecular Weight: 232.395
• Mol File: 93454-85-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Propanoic acid, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-methyl-, methyl ester, (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: Propanoic acid, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-methyl-, methyl ester, (S)-(93454-85-4)
• EPA Substance Registry System: Propanoic acid, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-methyl-, methyl ester, (S)-(93454-85-4)

Safety Data

• Hazardous Substances Data: 93454-85-4(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 104701-87-3 (2S)-3-(tert-butyl-dimethyl-silyloxy)-2-methyl-propanal 

Relevant articles and documents

N-Heterocyclic Carbene/Carboxylic Acid Co-Catalysis Enables Oxidative Esterification of Demanding Aldehydes/Enals, at Low Catalyst Loading

We report the discovery that simple carboxylic acids, such as benzoic acid, boost the activity of N-heterocyclic carbene (NHC) catalysts in the oxidative esterification of aldehydes. A simple and efficient protocol for the transformation of a wide range of sterically hindered α- and β-substituted aliphatic aldehydes/enals, catalyzed by a novel and readily accessible N-Mes-/N-2,4,6-trichlorophenyl 1,2,4-triazolium salt, and benzoic acid as co-catalyst, was developed. A whole series of α/β-substituted aliphatic aldehydes/enals hitherto not amenable to NHC-catalyzed esterification could be reacted at typical catalyst loadings of 0.02–1.0 mol %. For benzaldehyde, even 0.005 mol % of NHC catalyst proved sufficient: the lowest value ever achieved in NHC catalysis. Preliminary studies point to carboxylic acid-induced acceleration of acyl transfer from azolium enolate intermediates as the mechanistic basis of the observed effect.