103548-04-5

Basic information

• Product Name: Ethanone, 2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-phenyl-
• Synonyms: 2-(t-butyldimethylsilyloxy)-acetophenone;α-t-butyldimethylsilyloxy acetophenone;2-(tert-butyl-dimethylsilanyloxy)-1-phenylethanone;α-(tert-butyldimethylsilyloxy)acetophenone;2-(tert-butyldimethylsilyloxy)-1-phenylethanone;2-{[tert-butyl(dimethyl)silyl]oxy}-1-phenylethanone
• CAS NO: 103548-04-5
• Molecular Formula: C14H22O2Si
• Molecular Weight: 250.413
• Mol File: 103548-04-5.mol

Chemical Properties

• Melting Point: 73-74 °C
• Boiling Point: 294.4±23.0 °C(Predicted)
• Density: 0.955±0.06 g/cm3(Predicted)
• CAS DataBase Reference: Ethanone, 2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Ethanone, 2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-phenyl-(103548-04-5)
• EPA Substance Registry System: Ethanone, 2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-phenyl-(103548-04-5)

Safety Data

• Hazardous Substances Data: 103548-04-5(Hazardous Substances Data)

Upstream product

• 18162-48-6 tert-butyldimethylsilyl chloride 
• 98-86-2 acetophenone 
• 163667-14-9 2-(tert-butyldimethylsilyloxy)-2-phenylacetaldehyde 
• 73795-12-7 1-phenylprop-2-en-1-yl tert-butyldimethylsilyl ether 
• 71009-09-1 2-(tert-butyldimethylsilyl)oxy-1-phenylethanol 
• 582-24-1 1-phenyl-2-hydroxyethanone 
• 66324-10-5 tert-butyldimethyl(1-phenylvinyloxy)silane 

Downstream Products

• 98-86-2 acetophenone 
• 4432-63-7 2-phenylacrolein 
• 6006-81-1 3-hydroxy-2-phenylpropene 
• 936474-98-5 tert-butyl-dimethyl-(2-phenyl-allyloxy)-silane 
• 582-24-1 1-phenyl-2-hydroxyethanone 
• 1401226-49-0 5-(tert-butyldimethylsilanyloxymethyl)-5-phenylimidazolidine-2,4-dione 
• 166248-63-1 1'-phenyl-<1'-oxy>-2'-<<(1,1-dimethylethyl)dimethylsilyl>-oxy>ethane 
• 33868-51-8 2-hydroxymethyl-2-phenyl-1,3-dioxolane 
• 71009-09-1 2-(tert-butyldimethylsilyl)oxy-1-phenylethanol 
• 1264942-63-3 tert-butyldimethyl-(2-phenyl-[1,3]dioxolan-2-yl-methoxy)silane 
• 668475-40-9 (+/-)-9-[3-(t-butyldimethylsilyloxymethyl)-3-phenylpent-4-enyl]adenine 
• 668475-23-8 (+/-)-3-(t-butyldimethylsilyloxymethyl)-3-phenylpent-4-enoic acid ethyl ester 
• 668475-34-1 (+/-)-1-O-methanesulfonic acid 3-(t-butyldimethylsilyloxymethyl)-3-phenylpent-4-enyl ester 
• 668475-28-3 (+/-)-3-(t-butyldimethylsilyloxymethyl)-3-phenylpent-4-en-1-ol 

Relevant articles and documents

An alternative to the Swern oxidation

A variety of alcohols have been oxidized under mild conditions by the DMSO-Ph3P·X2 complexes. The reaction does not produce any Pummerer product. A mechanism for the reaction is proposed.

Synthetic applications of the amine-base treatment in the ozonolysis of substituted-allyl silyl ethers or -allyl esters via a novel ene-diol type rearrangement

The ozonolysis of substituted-allyl silyl ethers or -allyl esters followed by treatment with bases gave the corresponding α-silyloxy ketones or α-acyloxy ketones in good yields. The reaction is proposed to proceed via a novel ene-diol rearrangement of the corresponding α-silyloxy aldehydes or α-acyloxy aldehydes intermediates.

Cobalt-Catalyzed Reductive C-O Bond Cleavage of Lignin β-O-4 Ketone Models via in Situ Generation of the Cobalt-Boryl Species

An efficient and mild method for reductive C-O bond cleavage of lignin β-O-4 ketone models was developed to afford the corresponding ketones and phenols with PDI-CoCl2 as the precatalyst and diboron reagent as the reductant. The synthetic utility of the methodology was demonstrated by depolymerization of a polymeric model and gram-scale transformation. Mechanistic studies suggested that this transformation involves steps of carbonyl insertion, 1,2-Brook type rearrangement, β-oxygen elimination, and rate-limiting regeneration of the catalytic active Co-B species.

Rhodium-catalyzed synthesis of 1,2-dihydropyridine by a tandem reaction of 4-(1-acetoxyallyl)-1-sulfonyl-1,2,3-triazole

A tandem reaction of 4-(1-acetoxyallyl)-1-sulfonyl-1,2,3-triazole including formation of α-imino rhodium carbene, 1,2-migration of an acetoxy group and six electron electrocyclic ring closure was reported. The migration of the OAc group with excellent chemoselectivity was the crucial process, leading to the formation of 1,2-dihydropyridine specifically in up to 90% yield. Several transformations of the dihydropyridine product were also achieved illustrating the potential of the protocol in organic synthesis. Based on the observation of the intermediate, a plausible mechanism was proposed.

Green organocatalytic α-hydroxylation of ketones

An efficient and green method for the α-hydroxylation of substituted ketones has been developed. This method includes the in situ conversion of various ketones into the corresponding silyl enol ethers and their oxidation to the corresponding α-hydroxy ketones. Two protocols have been established leading either to protected α-hydroxy carbonyls or free α-hydroxy ketones. Both procedures are easy to follow and lead to good to high yields for a variety of ketones.

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