37170-49-3

Basic information

• Product Name: Propanoic acid, 2,2-dimethyl-, trimethylsilyl ester
• CAS NO: 37170-49-3
• Molecular Formula: C8H18O2Si
• Molecular Weight: 174.315
• Mol File: 37170-49-3.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: Propanoic acid, 2,2-dimethyl-, trimethylsilyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Propanoic acid, 2,2-dimethyl-, trimethylsilyl ester(37170-49-3)
• EPA Substance Registry System: Propanoic acid, 2,2-dimethyl-, trimethylsilyl ester(37170-49-3)

Safety Data

• Hazardous Substances Data: 37170-49-3(Hazardous Substances Data)

Upstream product

• 43112-38-5 3-(trimethylsilyl)-2-oxazolidinone 
• 75-98-9 Trimethylacetic acid 
• 7677-24-9 trimethylsilyl cyanide 
• 99377-16-9 2,2-Dimethyl-propionic acid (benzyl-dimethyl-silanyl)-methyl ester 

Downstream Products

• 598-98-1 Methyl pivalate 
• 3938-95-2 2,2-dimethyl-propanoic acid ethyl ester 
• 126980-33-4 4-chlorophenyl 2,2-dimethylpropionate 
• 132381-68-1 S-4-chlorophenyl 2,2-dimethylpropanethioate 
• 4920-92-7 pivalic acid phenyl ester 
• 60718-19-6 S-phenyl 2,2-dimethylpropanethioate 
• 144406-22-4 S-phenyl 4-trifluoromethylbenzenecarbothioate 
• 72569-06-3 2,2-dimethyl-propionic acid 3-methyl-phenyl ester 
• 132381-65-8 S-4-methoxyphenyl 2,2-dimethylpropanethioate 
• 85733-07-9 1-methyl-3-phenylpropyl 2,2-dimethylpropionate 
• 87228-44-2 3-phenyl-1-propyl 2,2-dimethylpropanoate 
• 75-98-9 Trimethylacetic acid 
• 501346-97-0 1-[N-(2-iodophenyl)amino]-4,4-dimethyl-3-pentanone 
• 75-77-4 chloro-trimethyl-silane 

Relevant articles and documents

Synthesis and Thermolysis of Ketal Derivatives of 3-Hydroxy-1,2-dioxolanes

3--3,4,4,5-tetramethyl-5-phenyl-1,2-dioxolane (2), 3-methoxy-3,4,4,5-tetramethyl-5-phenyl-1,2-dioxolane (3), and 3-acetoxy-3,4,4,5-tetramethyl-5-phenyl-1,2-dioxolane (4) were synthesized from the corresponding 3-hydroxy-1,2-dioxolane (1a) under basic conditions. 3-Acetoxy-4,4-dimethyl-3,5,5-triphenyl-1,2-dioxolane (5) was also synthesized via this approach.Under acidic conditions, 3-hydroxy-1,2-dioxolane 1a underwent quantitative decomposition to phenol and 3,3-dimethyl-2,4-pentanedione.This competing degradation was dependent on the nature of the substituents at position-5.Methyl groups at position-5 slowed the degradative rearrangement whereas phenyl groups favored it. 3-Methoxy- and 3-(allyloxy)-4,4,5,5-tetramethyl-3-phenyl-1,2-dioxolanes (6, 7) were synthesized under acidic conditions from the appropriate 1,2-dioxolane precursors and the corresponding alcohols.At 60 deg C, derivatized 1,2-dioxolanes 2-7 were found to be more stable than the corresponding 3-hydroxy-1,2-dioxolanes.The first order rate constants for the thermolysis of 1,2-dioxolanes 2-7 were determined.Product studies showed that thermolysis of 2-5 yielded pairs of ketones and derivatized carboxylic acids.In addition to R-group migration products, an acetoxy migration product was observed for the thermolysis of 4.Thermolysis of 6 at 60 deg C in benzene yielded methyl benzoate and pinacolone, quantitatively.Thermolysis of 7 yielded products analogous to those for 6.No evidence for internal trapping of radicals by the carbon-carbon double bond of the allyloxy group in 7 was found.The thermolysis appeared to proceed with peroxy bond homolysis as the rate-determining step.Subsequent β-scissions of the intermediate 1,5-oxygen diradical with interesting rearrangements that show a high preference for alkyl vs phenyl migration account for the observed product distributions.The results suggest that the β-scission/rearrangement mechanism may not be concerted but rather stepwise to yield 1,3-diradical and carbonyl fragments.

Reagents and synthetic methods. 31. Silylations with N-trimethylsilyl-2-oxazolidinone (TMSO)

Silylation of ketones, alcohols, mercaptans, and carboxylic acids with N-trimethylsilyl-2-oxazolidinone (TMSO) and triflic acid as catalyst has been described from synthetic and mechanistic points of view.