7381-30-8

Basic information

• Product Name: 1,2-Bis(trimethylsilyloxy)ethane
• Synonyms: 1,2-bis(trimethylsllyloxy)ethane;2,2,7,7-Tetramethyl-3,6-dioxa-2,7-disilaoctane;3,6-Dioxa-2,7-disilaoctane, 2,2,7,7-tetramethyl-;1,2-BIS(TRIMETHYLSILYLOXY)ETHANE;1,2-BIS(TRIMETHYLSILOXY)ETHANE;1,3-BIS(TRIMETHYLSILOXY)ETHANE;ETHYLENEDIOXYBIS(TRIMETHYLSILANE);ETHYLENE GLYCOL BIS(TRIMETHYLSILYL ETHER)
• CAS NO: 7381-30-8
• Molecular Formula: C₈H₂₂O₂Si₂
• Molecular Weight: 206.43
• EINECS: 230-950-3
• Product Categories: Industrial/Fine Chemicals;Monoalkoxysilanes;Protection & Derivatization Reagents (for Synthesis);Si (Classes of Silicon Compounds);Si-O Compounds;Synthetic Organic Chemistry
• Mol File: 7381-30-8.mol

Chemical Properties

• Boiling Point: 165-166 °C(lit.)
• Flash Point: 115 °F
• Appearance: Clear colorless to faint yellow/Liquid
• Density: 0.842 g/mL at 25 °C(lit.)
• Vapor Pressure: 2.46mmHg at 25°C
• Refractive Index: n20/D 1.403(lit.)
• Storage Temp.: Flammables area
• Sensitive: Moisture Sensitive
• BRN: 1744217
• CAS DataBase Reference: 1,2-Bis(trimethylsilyloxy)ethane(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Bis(trimethylsilyloxy)ethane(7381-30-8)
• EPA Substance Registry System: 1,2-Bis(trimethylsilyloxy)ethane(7381-30-8)

Safety Data

• Statements: 10
• Safety Statements: 23-24/25-16
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• F: 10-21
• TSCA: No
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 7381-30-8(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis Studies:
1,2-Bis(trimethylsilyloxy)ethane is used as a reagent for chemical synthesis, particularly in the preparation of various organic compounds. Its ability to form stable silyl ethers with alcohols and the ease of its synthesis make it a valuable intermediate in the synthesis of complex organic molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 1,2-Bis(trimethylsilyloxy)ethane is used as a protecting group for alcohols during organic synthesis. This application is crucial for the selective protection of functional groups in multi-step synthesis processes, ensuring the desired product is obtained without unwanted side reactions.
Used in Material Science:
1,2-Bis(trimethylsilyloxy)ethane is also utilized in the field of material science, particularly in the synthesis of silane-based materials and coatings. Its unique properties allow for the creation of materials with specific characteristics, such as improved adhesion, durability, and chemical resistance.
Used in Analytical Chemistry:
In analytical chemistry, 1,2-Bis(trimethylsilyloxy)ethane serves as a derivatizing agent for the analysis of various compounds, such as alcohols, carboxylic acids, and amines. The formation of silyl ethers can improve the volatility and stability of these compounds, making them more suitable for analysis using techniques like gas chromatography and mass spectrometry.
Overall, 1,2-Bis(trimethylsilyloxy)ethane is a versatile compound with a wide range of applications across different industries, including chemical synthesis, pharmaceuticals, material science, and analytical chemistry. Its unique properties and reactivity make it an essential tool in the development and production of various products and materials.

InChI:InChI=1/C8H22O2Si2/c1-11(2,3)9-7-8-10-12(4,5)6/h7-8H2,1-6H3

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 107-21-1 ethylene glycol 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 
• 110-71-4 1,2-dimethoxyethane 
• 16029-98-4 trimethylsilyl iodide 
• 1000-70-0 bis(trimethylsilyl)carbodi-imide 
• 123-91-1 1,4-dioxane 
• 4544-20-1 2-ethoxy-1,3-dioxolane 
• 107-46-0 Hexamethyldisiloxane 
• 21062-20-4 diglycolyl chloride 
• 1067-55-6 dibutyldimethoxytin 
• 3590-59-8 2,2-dibutyl[1,3,2]dioxastannolane 
• 10416-59-8 N,O-bis-(trimethylsilyl)-acetamide 
• 7677-24-9 trimethylsilyl cyanide 

Downstream Products

• 1119-86-4 1,2-decanediol 
• 1708-41-4 2-(furan-2-yl)-1,3-dioxolane 
• 83977-12-2 2-[(E)-2-phenylethenyl]-1,3-dioxolane 
• 52157-62-7 2-(5-bromothiophen-2-yl)-1,3-dioxolane 
• 77855-89-1 2,3,4,6-tetra-O-benzylspiro[1,5-anhydro-D-glucitol-1,2'-[1,3]dioxolane] 
• 1004-58-6 1,4-dioxa-spiro[4.5]dec-6-ene 
• 1708-34-5 2-hexyl-1,3-dioxolane 
• 7092-24-2 1,4-dioxaspiro<4.5>dec-7-ene 
• 105539-21-7 trans-retinal 1,3-dioxolane 
• 979-65-7 3-Ethylendioxy-pregnen-⁽⁴⁾-on-⁽²⁰⁾ 
• 978-98-3 20-ethylenedioxy-4-pregnen-3-one 
• 38223-75-5 4-(2-Methyl-[1,3]dioxolan-2-yl)-cyclohex-1-enecarbaldehyde 
• 105539-25-1 1-(4-[1,3]Dioxolan-2-yl-cyclohex-3-enyl)-ethanone 
• 94113-44-7 6-pentyl-1,4-dioxaspiro[4.4]nonane 

Relevant articles and documents

Synthesis method of 1, 2-bis (alkyl-siloxy) ethane

The invention provides a synthesis method of 1, 2-bis (alkyl-siloxy) ethane, and belongs to the technical field of battery electrolytic solution additives. The method comprises the following steps: adding dichloromethane and ethylene glycol into a reaction kettle, cooling to 15 DEG C or below, adding imidazole, continuously cooling to -15 DEG C or below, starting to dropwise add vinyl dimethyl chlorosilane or tert-butyl dimethyl chlorosilane or trimethylchlorosilane, controlling the temperature in the dropwise adding process to range from -15 DEG C to -25 DEG C, after dropwise adding is completed for 1.8-2.2 h, washing the system with water, carrying out liquid separation, drying, carrying out suction filtration, collecting dichloromethane under reduced pressure, and rectifying to obtain 1, 2-bis (dimethyl vinyl siloxy) ethane or 1, 2-bis (tert-butyl dimethyl siloxy) ethane or 1, 2-bis (trimethyl siloxy) ethane. The synthesis method is simple, and the yield of the synthesized product is high.

Pinacolatoboron fluoride (pinBF) is an efficient fluoride transfer agent for diastereoselective synthesis of benzylic fluorides

The incorporation of alkoxy ligands within a range of alkoxyfluoroboranes and dialkoxyfluoroboranes results in fluoroborane reagents with attenuated Lewis acidity and increased ability to donate fluoride ion(s) when compared to boron trifluoride itself. Pinacolatoboron fluoride (pinBF), prepared in situ from BF3·OEt2 and bis(O-trimethylsilyl)pinacol, has been identified as an efficient fluoride donor which allows highly stereoselective SN1-type epoxide ring-opening (with retention of configuration) of a range of trans-β-methyl-substituted aryl epoxides to give the corresponding syn-fluorohydrins. The substrate scope of this transformation is more broad than the analogous protocol using boron trifluoride alone.

Total synthesis of (-)-hippodamine by stereocontrolled construction of azaphenalene skeleton based on extended one-pot asymmetric azaelectrocyclization

The first asymmetric total synthesis of (-)-hippodamine has been accomplished via the concise construction of its azaphenalene core, which is featured by the 2,4,6-chiral piperidine synthesis based on one-pot asymmetric azaelectrocyclization in the partially activated substituent system and the subsequent intramolecular Mannich reaction.

The pentamethylcyclopentadienylsilicon(II) cation as a catalyst for the specific degradation of oligo(ethyleneglycol) diethers

Catalytic open sandwiches: Oligo(ethyleneglycol) diethers RO(CH 2CH2O)nR are degraded by the unusual catalyst Cp Si+ (see scheme). The open coordination sphere at silicon allows up to four Si-O contacts; crystal structure data of the reactive compounds [Cp Si(dme)]+BR4- and [Cp Si([12]crown-4)] +BR4- (R=C6F5) show weakly bound ether molecules. Copyright

METHOD OF MANUFACTURING (3R, 4S) -1- (4-FLUOROPHENYL) -3- [ (3S) -3- (4 -FLUOROPHENYL) -3-HYDROXYPROPYL) ] -4- (4-HYD ROXYPHENYL) -2-AZETIDINONE

A method of manufacturing (3R,4S)-l-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3- hydroxypropyl)]-4-(4-hydroxyphenyl)-2-azetidinone (Ezetimibe) of formula I, starting from the optically active (S)-N-acyl-oxazolidide of formula II, which is reacted with an alkyleneglycol of general formula III, (stage 1), and the obtained acetal-oxazolidide of general formula IV, is subjected to reaction with a silyl-imine of general formula V the produced amino-oxazolidide of general formula VI, (stage 3), and the obtained silylated azetidinone of general formula VII, is desilylated (stage 4), and the ketal of general formula VIII produced this way, is deketalized formula IX is finally reduced.

Ester dienolate [2,3]-Wittig rearrangement in natural product synthesis: Diastereoselective total synthesis of the triester of viridiofungin A, A 2, and A4

An ester dienolate [2,3]-Wittig rearrangement was utilized to access the alkylated citric acid skeleton 6 that is characteristic for the viridiofungins and other members of the alkyl citrate family of secondary natural products. The [2,3]-sigmatropic rearrangement of (Z,Z)-15 provided the rearrangement product (±)-syn-16 in moderate yield and with very good diastereoselectivity. A Julia-Kocienski olefination efficiently served to connect the polar head (±)-syn-26 with the lipophilic tail (32a-c) of the viridiofungins. Amide formation between the racemic viridiofungin precursors 35a-c and the enantiomerically pure amino acid L-tyrosine methyl ester followed by preparative reversed-phase HPLC provided the isopropyl dimethyl ester of viridiofungin A ((+)-39a), A2 ((+)-39b), and A4 ((+)-39c) as well as the nonnatural diastereomers (-)-38a-c.

A Convenient Procedure for the Synthesis of Acetals from α-Halo Ketones

A study for determining the scope and limitations of a procedure for synthesising ethylene acetals from haloketones is presented. The method uses 1,2-bis(trimethylsilyloxy)ethane, BTSE, as reagent and Nafion-TMS as catalyst. Two procedures have been tested: (A) stoichiometric amounts of the haloketone and BTSE and a catalytic amount of Nafion-TMS were heated to reflux in chloro-form solution, and (B) stoichiometric amounts of the reactants and a catalytic amount of Nafion-TMS were heated to 90-100°C in the absence of solvent. The following ketones have been tested: 2-bromo-1-phenyl-1-ethanone, 2-bromo-cyclopentenone, 3-bromo-3-methyl-2-butanone, 3-chloro-3-methyl-2-butanone, 1-bromo-3,3-dimethyl-2-butanone, 1-chloro-3,3-dimethyl-2-butanone, 2-bromocyclohexanone, 2-chloro-1-cyclohexyl-1-ethanone, 1,1-dibromo-3,3-dimethyl-2-butanone, 1,3-dibromo-3-methyl-2-butanone, 1,3-dibromo-2-butanone, 1,3-dibromo-2-propanone, 2-chloro-1-phenyl-1-ethanone, and endo-2-bromocamphor. Yields were in the range 57-100% with the exceptions of endo-2-bromocamphor which afforded 10% yield and the dibromoketones 1,1-dibromo-3,3-dimethyl-2-butanone and 1,3-dibromo-3-methyl-2-butanone for which the method failed. Factors determining the scope and limitations are briefly discussed. Full experimental details and spectroscopic data of the acetals are given.

Ring-opening reactions of cyclic acetals and 1,3-oxazolidines with halosilane equivalents

Reactions of acetal and 1,3-oxazolidine rings were examined using two kinds of iodosilane equivalent reagents, a 1:2 mixture of Me3SiNEt2 and MeI (reagent 1a) and a 1:1 mixture of Et3SiH and MeI containing a catalytic amount of PdCl2 (reagent 1b). In the reactions of alkanone ethylene acetals with reagent 1a, a C-O bond in the acetal ring readily cleaved to give 2-(trimethylsiloxy)ethyl enol ethers. Similarly, the C-O bond of 1,3-oxazolidine rings cleaved to give ring-opened imine or enamine derivatives. The reactions of aromatic ketone ethylene acetals and cyclohexanone trimethylene acetal led to deprotection of the acetal unit to liberate free ketones. With reagent 1b, cycloalkanone ethylene acetal afforded a dimeric product with 2-iodoethyl alkenoate moieties, while aromatic ketone ethylene or trimethylene acetals produced deprotected ketones.

Towards the diastereoselective functionalization of non-racemic acetal derivatives of η6-arylcarbonyl complexes of tricarbonylchromium

(S)-Butane-1,2,4-triol (2) has been investigated as a potential chiral auxiliary for the formation of non-racemic acetals derived from η6-arylcarbonyl complexes of tricarbonylchromium. Predominantly the cis dioxan (5) was formed from benzaldehyde, leading to preparation of the η6-Cr(CO)3 complex (16), and of the derived complexes (23) and (24). Lithiation-electrophile quenching of these complexes gave a mixture of products arising from ortho and benzylic functionalization. Reaction of acetophenone, or of the η6-Cr(CO)3 complexes (45) or (46), with either the triol (2) or its tris(silyl) ether (15) under conditions of kinetic or thermodynamic control gave an inseparable mixture of acetals.

Silicon-29 NMR spectra of tert-butyldimethylsilyl and trimethylsilyl derivatives of some non-rigid diols

29Si NMR spectra of trimethylsilyl (TMS) and tert-butyldimethylsilyl (TBDMS) derivatives of selected diols were measured under standardized conditions (i.e., in diluted CDCl3 solutions). Application of the recently reported correlation between the chemical shifts in TMS and TBDMS derivatives revealed considerable and systematic deviations which exceeded experimental errors and error estimates from the correlation. Two possible explanations of the deviations are considered: interaction between the two bulky substituent groups and invalidity of the reported correlation for simple hydroxy derivatives. An independent study of analogous derivatives of monohydroxy compounds has shown that the linear correlation holds but the slope and intercept are significantly different from those reported previously on the basis of a study of amino acid derivatives. The data obtained for the diol derivatives fit the new correlation very well and no indication of an interaction between the bulky TBDMS groups was noticed. However, deviations do occur in branched diol derivatives in which branching reduces accessibility of the oxygen atoms surface to associate with proton donors. The largest deviation was found when intramolecular hydrogen bond was formed.