148204-86-8

Basic information

• Product Name: Benzeneacetic acid, a-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, methyl ester
• Synonyms: methyl 2-(tert-butyldimethylsilyloxy)-2-phenylacetate;(tert-butyl-dimethyl-silanyloxy)-phenyl-acetic acid methyl ester;(R)-(-)-Methyl α-[((1,1-Dimethylethyl)dimethylsilyl)oxy]-benzeneacetate
• CAS NO: 148204-86-8
• Molecular Formula: C15H24O3Si
• Molecular Weight: 280.439
• Mol File: 148204-86-8.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 316.5±30.0 °C(Predicted)
• Density: 0.986±0.06 g/cm3(Predicted)
• CAS DataBase Reference: Benzeneacetic acid, a-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Benzeneacetic acid, a-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, methyl ester(148204-86-8)
• EPA Substance Registry System: Benzeneacetic acid, a-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, methyl ester(148204-86-8)

Safety Data

• Hazardous Substances Data: 148204-86-8(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 611-71-2 MANDELIC ACID 
• 58367-63-8 (Z)-β(tert.-Butyldimethylsilyloxy)-β-methoxystyrol 
• 4358-87-6 (RS)-methyl mandelate 
• 18162-48-6 tert-butyldimethylsilyl chloride 

Downstream Products

• 93-56-1 phenylethane 1,2-diol 
• 163667-14-9 2-(tert-butyldimethylsilyloxy)-2-phenylacetaldehyde 
• 371158-20-2 3-[(tert-butyldimethylsilyloxy)phenylmethyl]-1,5-diphenyl-1,4-pentadiyn-3-ol 
• 20907-13-5 2-methyl-1-phenylpropane-1,2-diol 
• 1004852-56-5 7-[(tert-butyldimethylsilyloxy)phenylmethyl]trideca-5,8-diyn-7-ol 
• 1021306-03-5 C₂₂H₂₈O₂Si 
• 1260146-96-0 C₂₂H₂₆O₂Si 
• 1260146-34-6 1-hydroxy-1,4-diphenylbut-3-yne-2-one 
• 1260146-54-0 1-hydroxy-1,4-diphenylbut-3-yne-2-one 
• 127388-13-0 1,4-diphenyl-3-butyne-1,2-dione 
• 176100-46-2 1-(naphthalen-2-yl)-4-phenylbutane-1,4-dione 
• 495-71-6 phenacylacetophenone 
• 132161-99-0 1-<(tert-Butyldimethylsilyl)oxy>-2-methyl-1-phenyl-2-propanol 
• 71009-10-4 2-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-ethanol 

Relevant articles and documents

Visible-Light-Induced Cycloaddition of α-Ketoacylsilanes with Imines: Facile Access to β-Lactams

We report the synthesis of β-lactams from α-ketoacylsilanes and imines, which proceeds via a formal [2+2] photochemical cycloaddition with in situ generation of siloxyketene. This mild and operationally simple reaction proceeds in an atom-economic fashion with broad substrate scope, including aldimines, ketimines, hydrazones, and fused nitrogen heterocycles, affording a variety of important β-lactams with satisfactory diastereoselectivities in most cases. This reaction also features good functional-group tolerance, facile scalability and product diversification. Experimental and computational studies suggest that α-ketoacylsilanes can serve as photochemical precursors by engaging in a 1,3 silicon shift to the distal carbonyl group.

Enantioselective aerobic oxidation of α-hydroxy-ketones catalyzed by oxidovanadium(V) methoxides bearing chiral, N-salicylidene- tert -butylglycinates

Chiral oxidovanadium(V) methoxides prepared from 3,5-disubstituted-N- salicylidene-l-tert-butylglycines and vanadyl sulfate in air-saturated MeOH serve as highly enantioselective catalysts for asymmetric aerobic oxidations and kinetic resolution of alkyl, aryl, and heteroaryl α-hydroxy-ketones with differed α-substituents at ambient temperature in toluene or TBME (tert-butyl methyl ether). The best scenarios involve the use of complexes which bear the tridendate templates derived from 3,5-diphenyl- or 3-o-biphenyl-5-nitro-salicyaldehyde. The kinetic resolution selectivities of the aerobic oxidation process are in the range of 12 to >1000 based on the selectivity factors (krel).

Synthesis of optically active α-hydroxycarbonyl compounds by (salen)Mn(III)-catalyzed oxidation of silyl enol ethers and silyl ketene acetals

Optically active α-hydroxy ketones and esters have been prepared by (salen)Mn(III)-catalyzed asymmetric oxidation of silyl enol ethers and silyl ketene acetals in high enantioselectivity, with ee values up to 81% for the α-hydroxy ketones and up to 57% for α-hydroxy esters. The extent of conversion and the enantioselectivity depends strongly on the type of oxygen donor, the pH of the aqueous bleach medium, the additive, and the substitution pattern at the enol functionality.