16654-46-9

Basic information

• Product Name: 3,6,9-Trioxa-2-silaundecane, 2,2-dimethyl-
• Synonyms: 3,6,9-Trioxa-2-silaundecane, 2,2-dimethyl-;2,2-Dimethyl-3,6,9-trioxa-2-silaundecane
• CAS NO: 16654-46-9
• Molecular Formula: C₉H₂₂O₃Si
• Molecular Weight: 206.35
• Mol File: 16654-46-9.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3,6,9-Trioxa-2-silaundecane, 2,2-dimethyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 3,6,9-Trioxa-2-silaundecane, 2,2-dimethyl-(16654-46-9)
• EPA Substance Registry System: 3,6,9-Trioxa-2-silaundecane, 2,2-dimethyl-(16654-46-9)

Safety Data

• Hazardous Substances Data: 16654-46-9(Hazardous Substances Data)

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 197356-78-8 2-[2-(2-Ethoxy-ethoxy)-ethoxy]-2,3,3,3-tetrafluoro-propionic acid 2-(2-ethoxy-ethoxy)-ethyl ester 
• 197356-81-3 trimethylsilyl 2-[2-(2-ethoxyethoxy)ethoxy]-2,3,3,3-tetrafluoropropionate 

Relevant articles and documents

Synthesis of Trifluorovinyl Ethers Incorporating Functionalized Hydrocarbon Ether Groups: Insight into the Mechanism of Trifluorovinyl Ether Formation from Trimethylsilyl 2-Alkoxy-2,3,3,3-tetrafluoropropionates

Novel trifluorovinyl ethers (TFVEs, ROCF=CF2), where R is an oligoether, were synthesized from the corresponding sodium alkoxide and hexafluoropropene oxide.The sodium alkoxide ring opened hexafluoropropene oxide at the more highly substituted carbon (C2) to give 2-alkoxy-2,3,3,3-tetrafluoropropionic acid ester incorporating 2 equiv of the alcohol, ROCF(CF3)CO2R.Hydrolysis of the ester and reaction of the resulting sodium 2-alkoxy-2,3,3,3-tetrafluoropropionate with chlorotrimethylsilane gave the trimethylsilyl 2-alkoxy-2,3,3,3-tetrafluoropropionate, ROCF(CF3)CO2Si(CH3)3.Gas phase vacuum thermolysis of the trimethylsilyl ester at 140-150 deg C gave the corresponding TFVEs in 55-63percent yields.Thus, 1--1,2,2-trifluoroethene and 1--1,2,2-trifluoroethene were synthesized from 2-(2-ethoxyethoxy)ethanol and 2-(2-tert-butoxyethoxy)ethanol, respectively.Interestingly, thermolysis of sodium or potassium 2-alkoxy-2,3,3,3-tetrafluoropropionates resulted in negligible to low yields of TFVEs.1 For example, thermolysis of sodium 2--2,3,3,3-tetrafluoropropionate gave a trifluoroacetate ester, 2-(2-ethoxyethoxy)ethyl trifluoroacetate.Variable temperature 19F NMR spectroscopy of trimethylsilyl 2--2,3,3,3-tetrafluoropropionate suggests that an equilibrium exists between two structural conformations of these trimethylsilyl esters: one in which there is an intramolecular "interaction" of silicon with fluorine and one in which there is no silicon-fluorine interaction.This interaction may affect the outcome of the trimethylsilyl ester thermolysis.