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Trimethyl(oxiran-2-yl)silane, also known as 2-(Trimethylsilyl)oxirane, is an organosilicon compound with the chemical formula C5H12OSi. It is a colorless liquid that is soluble in organic solvents and is commonly used as a protecting group in organic synthesis, particularly for alcohols. The compound is formed by the reaction of trimethylsilyl chloride with epoxides, and it can be easily removed under mild acidic conditions, making it a valuable tool in the synthesis of complex organic molecules. It is also used as a coupling agent in the production of silicone-based materials and as a reagent in the preparation of various organosilicon compounds. Due to its reactivity and potential hazards, it is important to handle Trimethyl(oxiran-2-yl)silane with care and in accordance with proper safety protocols.

16722-09-1

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16722-09-1 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 16722-09-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,6,7,2 and 2 respectively; the second part has 2 digits, 0 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 16722-09:
(7*1)+(6*6)+(5*7)+(4*2)+(3*2)+(2*0)+(1*9)=101
101 % 10 = 1
So 16722-09-1 is a valid CAS Registry Number.
InChI:InChI=1/C5H12OSi/c1-7(2,3)5-4-6-5/h5H,4H2,1-3H3

16722-09-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name trimethyl(oxiran-2-yl)silane

1.2 Other means of identification

Product number -
Other names 1,2-epoxyethyltrimethylsilane

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:16722-09-1 SDS

16722-09-1Upstream product

16722-09-1Relevant academic research and scientific papers

Vinylidene Homologation of Boronic Esters and its Application to the Synthesis of the Proposed Structure of Machillene

Fordham, James M.,Grayson, Matthew N.,Aggarwal, Varinder K.

supporting information, p. 15268 - 15272 (2019/10/21)

Alkenyl boronic esters are important reagents in organic synthesis. Herein, we report that these valuable products can be accessed by the homologation of boronic esters with lithiated epoxysilanes. Aliphatic and electron-rich aromatic boronic esters provided vinylidene boronic esters in moderate to high yields, while electron-deficient aromatic and vinyl boronic esters were found to give the corresponding vinyl silane products. Through DFT calculations, this divergence in mechanistic pathway has been rationalized by considering the stabilization of negative charge in the C?Si and C?B bond breaking transition states. This vinylidene homologation was used in a short six-step stereoselective synthesis of the proposed structure of machillene, however, synthetic and reported data were found to be inconsistent.

Method for synthesizing 2-phenyl-2-trimethylsilyl acetyl chloride from trimethyl (vinyl) silane

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Paragraph 0008-0010, (2018/05/01)

The invention relates to a method for synthesizing 2-phenyl-2-trimethylsilyl acetyl chloride from trimethyl (vinyl) silane, to mainly solve the technical problem that an industrial synthesis method ofthe compound is in shortage. The method comprises the following three steps: step 1, dissolving trimethyl(vinyl)silane in dichloromethane, and adding 3-chloroperoxybenzoic acid at a low temperature for reaction to obtain trimethyl (2-epoxyethyl)silane; step 2, dissolving phenyl magnesium bromide and cuprous cyanide in isopropyl ether at a low temperature, and adding trimethyl(2-epoxyethyl)silanefor reaction to generate 2-phenyl-2-trimethylsilyl ethanol; step 3, carrying out a reaction of a tetrahydrofuran solution of the 2-phenyl-2-trimethylsilyl ethanol under the condition with triethylamine and triphosgene to generate 2-phenyl-2-trimethylsilyl acetyl chloride.

CARBON DIOXIDE ABSORBENT AND METHOD OF USING THE SAME

-

Page/Page column 32, (2011/02/24)

In accordance with one aspect, the present invention provides an amino-siloxane composition comprising at least one of structures I, II, III, IV or V said compositions being useful for the capture of carbon dioxide from gas streams such as power plant flu

The (2-Phenyl-2-trimethylsilyl)ethyl-(PTMSEL)-Linker in the Synthesis of Glycopeptide Partial Structures of Complex Cell Surface Glycoproteins

Wagner, Michael,Dziadek, Sebastian,Kunz, Horst

, p. 6018 - 6030 (2007/10/03)

The (2-phenyl-2-trimethylsilyl)ethyl-(PTMSEL) linker represents a novel fluoride-sensitive anchor for the solid-phase synthesis of protected peptides and glycopeptides. Its cleavage is achieved under almost neutral conditions using tetrabutylammonium fluo

The (2-phenyl-2-trimethylsilyl) ethyl-(PTMSEL) linker - A novel linker for the solid-phase synthesis of protected peptides and glycopeptides cleavable with fluoride

Wagner, Michael,Kunz, Horst

, p. 317 - 321 (2007/10/03)

Suitable for the immobilization of carboxylic acids, the (2-phenyl-2-trimethylsilyl)ethyl linker was developed as a novel, fluoride-sensitive anchor. Cleavage with tetrabutylammonium fluoride (TBAF) trihydrate in CH2Cl2 under almost

(2-Phenyl-2-trimethylsilyl)ethyl (PTMSE) esters - A novel carboxyl protecting group

Wagner, Michael,Kunz, Horst

, p. 400 - 402 (2007/10/03)

A novel silicon-containing protecting group based on the known 2- (trimethylsilyl)ethyl system has been developed for the protection of the carboxylic group, e.g. in peptide chemistry. The new protecting group can be cleaved by treatment with tetra-n-butylammonium fluoride much more rapidly than the known 2-(trimethylsilyl)ethyl group, leading to less side reactions.

The (2-phenyl-2-trimethylsilyl)ethoxycarbonyl (Psoc) group - A novel amino protecting group

Wagner,Heiner,Kunz

, p. 1753 - 1756 (2007/10/03)

A novel silicon containing protecting group has been developed based on the known 2-(trimethylsilyl)ethyl system. The new protecting group is cleaved under very mild conditions by treatment with tetra-n-butylammonium fluoride in CH2Cl2 much more rapidly than the 2-(trimethylsilyl)ethoxycarbonyl group, leading to less side reactions.

Regiospecific Synthesis of 1-Silyl Substituted 1,4-Dienes

Schaumann, Ernst,Kirschning, Andreas

, p. 419 - 421 (2007/10/02)

The reaction of epoxysilanes with lithiated allylsilanes gives predominantly α-silyl-substituted alcohols (3) which are convenient precursors for the preparation of 1-silyl-substituted 1,4-dienes.

AN EFFICIENT METHOD FOR PREPARATION OF TRIMETHYLSILYL ETHYLENE OXIDE AND SOME OTHER TRIMETHYLSILYL OXIRANES

Jankowski, P.,Masnyk, M.,Wicha, J.

, p. 873 - 880 (2007/10/02)

Trimethylsilyl ethylene oxide and other α,β-epoxysilanes were obtained from corresponding (trimethylsilyl)alkenes by an one-pot procedure involving successive treatment with N-bromosuccinimide and aqueous sodium hydroxide.

Organosilicon compounds with functional groups proximate to silicon. XVII. Synthetic and mechanistic aspects of the lithiation of α,β-epoxyalkylsilanes and related α-heterosubstituted epoxides

Eisch, John J.,Galle, James E.

, p. 293 - 314 (2007/10/02)

A series of α-heterosubstituted epoxides, , has been found to undergo lithiation in the temperature range of -75 to -115 deg C at the C-H bond of the epoxide.The substituent Z could be Me3Si, Ph3Si, n-Bu3Sn, Ph3Sn, PhSO2, (OEt)2PO and Ph; the groups R and R' were H, Ph and n-C6H13; and the lithiating reagents were n-butyllithium, t-butyllithium and lithium diisopropylamide in donor media of THF or TMEDA.The lithiation occurs with retention of configuration and the resulting lithio-epoxide is unstable above 0 deg C, decomposing in a carbenoid manner.The lithiation is facile except for compounds where Z and R (an alkyl or aryl) are cis-oriented; where Z = R3Sn, lithiation occurs by tin-lithium, rather than hydrogen-lithium, exchange.The lithio-epoxides thereby generated can be quenched with various reagents to yield epoxides where the epoxide H has been replaced by D, Me3Sn, R, RCO and COOH.The utility of this procedure in organic synthesis is emphasized.Finally, the possible explanations for the acidity of such α-heterosubstituted epoxides and for the relative stability of the derived lithio-epoxides are considered and assessed.

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