Description

1-(tert-Butyldimethylsilyloxy)-2-propanone (CAS No. 74685-00-0) is a high-purity organosilicon compound with the molecular formula C₉H₂₀O₂Si, widely used in organic synthesis and pharmaceutical research. This reagent features a tert-butyldimethylsilyl (TBS) protecting group, making it invaluable for the selective protection of hydroxyl groups in complex molecular architectures. Its IUPAC name, 1-[tert-butyl(dimethyl)silyl]oxypropan-2-one, reflects its precise chemical structure, ensuring clarity for researchers. With excellent stability under various reaction conditions, this compound is ideal for nucleophilic additions, Grignard reactions, and other critical transformations. Packaged under inert conditions to guarantee purity and longevity, it is a must-have for laboratories focused on advanced synthetic chemistry.

Properties

• CAS Number: 74685-00-0
• Complexity: 168
• IUPAC Name: 1-[tert-butyl(dimethyl)silyl]oxypropan-2-one
• InChI: InChI=1S/C9H20O2Si/c1-8(10)7-11-12(5,6)9(2,3)4/h7H2,1-6H3
• InChI Key: LHYDYTSJUGPFLA-UHFFFAOYSA-N
• Exact Mass: 188.123256411
• Molecular Formula: C9H20O2Si
• Molecular Weight: 188.34
• SMILES: CC(=O)CO[Si](C)(C)C(C)(C)C
• Topological: 26.3
• Monoisotopic Mass: 188.123256411
• Synonyms: 74685-00-0, 1-(tert-Butyldimethylsilyloxy)-2-propanone, DTXSID90399591, DTXCID70350448, 1-((tert-Butyldimethylsilyl)oxy)propan-2-one, 1-[tert-butyl(dimethyl)silyl]oxypropan-2-one, MFCD01321330, SCHEMBL1085871, SCHEMBL22033623, 2-Propanone, 1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, LHYDYTSJUGPFLA-UHFFFAOYSA-N, [t-butyl(dimethyl)silyloxy]acetone, AKOS015913601, 1-(t-butyldimethylsilyloxy)-2-propanone, AS-40102, SY043365, 1-(tert-butyldimethylsilyloxy)propan-2-one, 1-{[tert-butyl (dimethyl)silyl]oxy}acetone, 1-{[tert-butyl(dimethyl)-silyl]oxy}acetone, CS-0112903, 1-[(tert-Butyldimethylsilyl)oxy]-2-propanone, 1-{[t-butyl(dimethyl)silyl]oxy}-2-propanone, 1-{[tert-Butyl(dimethyl)silyl]oxy}propan-2-one, 1-(tert-Butyldimethylsilyloxy)-2-propanone, 98%

Application

1-(tert-Butyldimethylsilyloxy)-2-propanone is primarily employed as a key intermediate in the synthesis of complex organic molecules, particularly in pharmaceutical and agrochemical research. Its TBS-protected hydroxyl group enables selective deprotection strategies, facilitating multi-step synthetic routes. Researchers utilize this compound in ketone-based transformations, including aldol condensations and reductive aminations. It also serves as a precursor for chiral building blocks in asymmetric synthesis. Its stability and reactivity make it a versatile tool for medicinal chemists and material scientists.

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