1825-63-4

Basic information

• Product Name: Trimethyl(propoxy)silane
• Synonyms: Propyloxytrimethylsilane;Silane, trimethylpropoxy-;trimethylpropoxy-silan;Trimethylpropoxysilane;trimethylpropoxy-Silane;PROPYL TRIMETHYLSILYL ETHER;PROPOXYTRIMETHYLSILANE;TRIMETHYL-N-PROPOXYSILANE
• CAS NO: 1825-63-4
• Molecular Formula: C₆H₁₆OSi
• Molecular Weight: 132.28
• EINECS: 217-371-1
• Product Categories: Chemical Synthesis;Organometallic Reagents;Organosilicon;Siloxanes
• Mol File: 1825-63-4.mol

Chemical Properties

• Melting Point: <0°C
• Boiling Point: 100-101 °C735 mm Hg(lit.)
• Flash Point: 28 °F
• Appearance: /
• Density: 0.762 g/mL at 25 °C(lit.)
• Vapor Pressure: 40.2mmHg at 25°C
• Refractive Index: n20/D 1.384(lit.)
• BRN: 1732553
• CAS DataBase Reference: Trimethyl(propoxy)silane(CAS DataBase Reference)
• NIST Chemistry Reference: Trimethyl(propoxy)silane(1825-63-4)
• EPA Substance Registry System: Trimethyl(propoxy)silane(1825-63-4)

Safety Data

• Hazard Codes: F
• Statements: 11
• Safety Statements: 16-23-24/25
• RIDADR: UN 1993 3/PG 2
• WGK Germany: 3
• F: 10-21
• TSCA: Yes
• HazardClass: 3.1
• PackingGroup: II
• Hazardous Substances Data: 1825-63-4(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Trimethyl(propoxy)silane is used as a reagent in metal-catalyzed cross-coupling reactions for its ability to facilitate the formation of carbon-carbon and carbon-heteroatom bonds. Its role as a ligand in these reactions is crucial for the synthesis of complex organic molecules.
Used in Pharmaceutical Development:
In the pharmaceutical industry, Trimethyl(propoxy)silane is utilized as a key intermediate in the synthesis of various drug molecules, contributing to the development of new medications.
Used in Specialty Chemicals Production:
Trimethyl(propoxy)silane is employed in the production of specialty chemicals, where its unique properties are leveraged to create high-value products with specific applications.
Used in Electronics Industry as a Coating Agent:
In the electronics sector, Trimethyl(propoxy)silane serves as a coating agent, providing protective layers on electronic components due to its chemical stability and other beneficial properties.

InChI:InChI=1/C6H16OSi/c1-5-6-7-8(2,3)4/h5-6H2,1-4H3

Upstream product

• 71-23-8 propan-1-ol 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 
• 75-77-4 chloro-trimethyl-silane 
• 27607-77-8 trimethylsilyl trifluoromethanesulfonate 
• 56002-71-2 trimethyl-(1H,1H,7H-dodecafluoroheptyloxy)silane 
• 56002-69-8 trimethyl-(1H,1H,3H-tetrafluoropropoxy)silane 
• 56002-63-2 trimethyl-(1H,1H,5H-octafluoropentyloxy)silane 
• 104915-79-9 trimethyl-(1H,1H,9H-hexadecafluorononyloxy)silane 
• 109-95-5 ethyl nitrite 
• 1825-62-3 ethyl trimethylsilyl ether 
• 107-31-3 Methyl formate 
• 543-67-9 n-propyl nitrite 
• 1825-61-2 Trimethylmethoxysilane 
• 110-74-7 propyl methanoate 

Downstream Products

• 667-18-5 C₉H₁₂FO₂P 
• 56859-43-9 C₉H₁₂F₃OP 
• 1825-61-2 Trimethylmethoxysilane 
• 71352-49-3 2-n-propoxycyclohex-2-enone 
• 139332-48-2 Benzoic acid (2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-propoxy-tetrahydro-pyran-3-yl ester 
• 13040-68-1 n-propyl dichlorophosphite 
• 7244-77-1 1-nitro-4-propoxybenzene 
• 1912-31-8 propyl methanesulfonate 

Relevant articles and documents

Air- And Water-Tolerant (PNP)Ir Precatalyst for the Dehydrogenative Borylation of Terminal Alkynes

This work discloses the facile synthesis and efficacy of (PNP)IrH(OAc), a precatalyst for the dehydrogenative borylation of terminal alkynes (DHBTA). Unlike the previously reported precatalysts in the (PNP)Ir system (PNP = diarylamido/bis(phosphine) pincer), it is air-stable in the solid state. Upon exposure to air in solution, it possesses a useful half-life on the order of 1-100 h, depending on the intensity of mixing. Air-degraded solutions of (PNP)IrH(OAc) retain DHBTA catalytic activity and selectivity upon exposure to the mixture of a terminal alkyne and HBpin. It is also demonstrated that (PNP)Ir-catalyzed DHBTA is compatible with the presence of modest amounts of moisture or air and that the catalyst is sufficiently long-lived to deliver turnover numbers (TONs) of > 100 ?000.

Synthesis and characterization of a bifunctional nanomagnetic solid acid catalyst (Fe3O4@CeO2/SO42?) and investigation of its efficiency in the protection process of alcohols and phenols via hexamethyldisilazane under solvent-free conditions

In this research, Fe3O4@CeO2 (FC) was synthesized using the coprecipitation method and functionalized by an ammonium sulfate solution to achieve a heterogeneous solid acid Fe3O4@CeO2/SO42? (FCA) catalyst. The synthesized bifunctional catalyst was used in the protection process of alcohols and phenols using hexamethyldisilazane (HMDS) at ambient temperature under solvent-free conditions. Due to its excellent magnetic properties, FCA can easily be separated from the reaction mixture and reused several times without significant loss in its catalytic activity. Excellent yield and selectivity, simple separation, low cost, and high recyclability of the nanocatalyst are outstanding advantages of this procedure. The characterization was carried out using different techniques such as Fourier transform infrared spectroscopy (FT-IR), scanning electron microscopy (SEM), energy dispersive X-ray spectroscopy (EDX), X-ray diffraction (XRD), and vibrating sample magnetometry (VSM).

Nanomagnetic zirconia-based sulfonic acid (Fe3O4@ZrO2-Pr-SO3H): A new, efficient and recyclable solid acid catalyst for the protection of alcohols: Via HMDS under solvent free conditions

In the present work, sulfonic acid functionalized nanomagnetic zirconia is prepared by the reaction of (3-mercaptopropyl)trimethoxysilane and nanomagnetic zirconia. Then, nanomagnetic zirconia-based sulfonic acid (Fe3O4@ZrO2/su

Ligand survey results in identification of PNP pincer complexes of iridium as long-lived and chemoselective catalysts for dehydrogenative borylation of terminal alkynes

Following the report on the successful use of SiNN pincer complexes of iridium as catalysts for dehydrogenative borylation of terminal alkynes (DHBTA) to alkynylboronates, this work examined a wide variety of related pincer ligands in the supporting role in DHBTA. The ligand selection included both new and previously reported ligands and was developed to explore systematic changes to the SiNN framework (the 8-(2-diisopropylsilylphenyl)aminoquinoline). Surprisingly, only the diarylamido/bis(phosphine) PNP system showed any DHBTA reactivity. The specific PNP ligand (bearing two diisopropylphosphino side donors) used in the screen showed DHBTA activity inferior to SiNN. However, taking advantage of the ligand optimization opportunities presented by the PNP system via the changes in the substitution at phosphorus led to the discovery of a catalyst whose activity, longevity, and scope far exceeded that of the original SiNN archetype. Several Ir complexes were prepared in a model PNP system and evaluated as potential intermediates in the catalytic cycle. Among them, the (PNP)Ir diboryl complex and the borylvinylidene complex were shown to be less competent in catalysis and thus likely not part of the catalytic cycle.

Silylation of hydroxy groups with HMDS under microwave irradiation and solvent-free conditions

Phenols and alcohols are silylated with hexamethyldisilazane (HMDS) under microwave irradiation in solvent-free condition in good to excellent yields.

Silicon-29 NMR spectra of trimethylsilylated alcohols

29Si NMR spectra of trimethylsilyl (TMS) derivatives of 26 simple alcohols were measured under standardized conditions (i.e., in sufficiently diluted deuteriochloroform solutions). Due to association with the solvent the chemical shifts are in almost all cases larger than those reported earlier for different solutions. This observation is in agreement with the proposed mechanism of steric effects as being due to sterically controlled association with the solvent. The use of chloroform as a solvent enhances steric effects hut at the same time it can reduce small differences due to polar effects in closely related compounds. In the studied class of compounds the gross dependence of the chemical shift on polar effects is not substantially affected by the change of the solvent.

Carbohydrates as chiral auxiliaries: Synthesis of 2-hydroxy-β-D-glucopyranosides

A new 2-step, 1-pot procedure for the stereoselective glycosylation of allylic alcohols with 1,2-di-O-benzoyl-β-D-glucopyranosides to produce 2-hydroxy-β-D-glucopyranosides has been developed. The required precursor for the glycosylation was readily obtained from tri-O-benzyl-D-glucal in 2 steps (91% overall).

SYNTHESIS OF DIOSPHENOL ETHERS BY MEANS OF ALKOXYTRIMETHYLSILANES

α-Diketones may be O-alkylated with a variety of alkoxytrimethylsilanes.

A New Four-centre Reaction of Alkanol-Alkoxide Negative Ions. The Reaction of with Alkoxysilanes. An Ion Cyclotron Resonance Study

Alkanol-alkoxide negative ions 1O...H...OR2>(-) react with alkoxysilanes Me3SiOR3 to produce both 1O(-)> and 2O(-)> ions of trigonal bipyramidal geometry.When R1 2 and either R1 or R2 >= Pr, the four-center reaction 1O...H...OR2>(-) + Me3SiOR3 -> 2O...H...OR3>(-) + Me3SiOR1 is observed.Addition of 1O...H...OR2>(-) in the reverse direction is not detected.Analogous reactions do not occur between Me3SiX and 1O...H...OR2>(-) when X = F, NHR, NR2, SiMe3, alkyl, allyl, propargyl, benzyl, or aryl, but 1O...H...X>(-) ions of small abundance are formed when X = HO, OCOMe, OCN, and SR.Cyclic ethers react with alkanol-alkoxyde negative ions by reaction (i;n = 2-4).