33861-17-5

Usage

Uses

Used in Selenation Applications:
TRIMETHYL(PHENYLSELENO)SILANE is used as a selenating reagent for the introduction of selenium into various organic compounds. This is particularly useful in the synthesis of organoselenium compounds, which have found applications in various fields such as pharmaceuticals, agrochemicals, and materials science.
Used in Synthesis of Benzeneselenol:
TRIMETHYL(PHENYLSELENO)SILANE is used as a precursor in the synthesis of benzeneselenol, an important intermediate in the production of various organoselenium compounds. Benzeneselenol can be further functionalized to obtain a wide range of organoselenium derivatives with diverse applications.
Used in Introduction of Phenylseleno Function:
TRIMETHYL(PHENYLSELENO)SILANE is used as a reagent for the introduction of the phenylseleno function into a variety of oxygen-containing compounds. This allows for the synthesis of a broad range of organoselenium-containing molecules with potential applications in various industries, such as pharmaceuticals, where they may exhibit biological activities or improve the properties of existing compounds.

Preparation

Phenyl Trimethylsilyl Selenide is conveniently prepared by the reduction of diphenyl diselenide with sodium in THF, followed by silylation of thus formed PhSeNa with chlorotrimethylsilane. In a small scale reaction, silylation of PhSeLi, which can be prepared in situ from metallic selenium and phenyllithium in THF, is alternatively utilized.

InChI:InChI=1/C9H14SeSi/c1-11(2,3)10-9-7-5-4-6-8-9/h4-8H,1-3H3

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 1666-13-3 diphenyl diselenide 
• 52251-58-8 lithium phenylselenide 
• 645-96-5 Benzeneselenol 
• 993-07-7 trimethylsilan 
• 29680-62-4 Tris(phenylseleno)borane 
• 72017-00-6 Thallous Phenyl Selenide 

Downstream Products

• 74206-95-4 3-phenylseleno-1-butanal 
• 70678-09-0 3-Phenylseleno-1-buten-1yl-trimethylsilylether 
• 74206-94-3 α-Phenylselenosilylether 
• 16029-98-4 trimethylsilyl iodide 
• 29680-62-4 Tris(phenylseleno)borane 
• 61501-53-9 C₁₈H₁₅AsSe₃ 
• 58558-73-9 Triphenylselenophosphit 
• 74206-93-2 [(4-Methoxy-phenyl)-phenylselanyl-methoxy]-trimethyl-silane 
• 71766-34-2 C₁₆H₁₈S₂Se₂ 
• 70737-26-7 4-(phenylselenyl)butan-2-one 
• 78905-72-3 4-Phenylseleno-2-buten-2-yl-trimethylsilylether 
• 118793-20-7 Trimethyl-(3-phenylselanyl-propoxy)-silane 
• 118793-12-7 Trimethyl-(4-phenylselanyl-butoxy)-silane 
• 118793-17-2 Trimethyl-(2-methyl-4-phenylselanyl-butoxy)-silane 

Relevant academic research and scientific papers

Selenenate Anions (PhSeO?) as Organocatalyst: Synthesis of trans-Stilbenes and a PPV Derivative

The selenenate anion (RSeO?) is introduced as an active organocatalyst for the dehydrohalogen coupling of benzyl halides to form trans-stilbenes. It is shown that RSeO? is a more reactive catalyst than the previously reported sulfur analogues (sulfenate anion, RSO?) and selenolate anions (RSe?) in the aforementioned reaction. This catalytic system was also applied to the benzylic-chloromethyl-coupling polymerization (BCCP) of a bis-chloromethyl arene to form ppv (poly(p-phenylene vinylene))-type polymers with high yields, Mn (average molecular weight) up to 13,000 and ? (dispersity) of 1.15. (Figure presented.).

Reactions of RSe-EMe3 (E = Si, Ge, Sn, Pb) with XeF2 - RSe-F equivalents in the fluoroselenenylation of acetylenes

Selenides of the type R1Se-EMe3 (E = Si, Ge, Sn, Pb) react with xenon difluoride by cleavage of the Se-E bond to yield the R1Se-F intermediate and the fluorides Me3E-F, whereas the Se-C bond in PhSe-tBu (E = C) is stable against XeF2. The presence of R1Se-F intermediates is confirmed by addition to acetylenes (4-octyne, 3-hexyne). Thus, the fluoroselenenylation of acetylenes gives fluoro(organylseleno)olefins in preparative yields. In the cases of E = Si, Ge, Sn, and Pb, aryl and n-alkyl groups are suitable as the substituent R1. The X-ray crystal structural analysis of (E)-3-(p- carboxyphenylseleno)-4-fluorohex-3-ene - the first example of an uncharged fluoroselenoolefin synthesized from p-EtO2C-C6H4-Se-SnMe3, XeF2, and 3- hexyne followed by an ester hydrolysis - shows that the addition of the selenenylfluoride intermediate to the acetylene proceeds via a trans- addition, as is known for the R2Se2-XeF2 reagents.

Generation and Mesolysis of PhSeSiR3.-: Mechanistic Studies by Laser Flash Photolysis and Application for Bimolecular Group Transfer Radical Reactions

The investigation presented in this paper explores the mechanistic aspects and synthetic potentials of PET promoted reductive activation of selenosilane 1a to its radical anion 1a.-. PET activation of 1a is achieved through a photosystem comprising a light-absorbing electron-rich aromatic (ERA), such as DMN or DMA, as an electron donor and ascorbic acid as a co-oxidant. The evidence for the ET from excited singlet states of DMN as well as DMA to 1a is suggested by estimating negative ΔGet (-51 and -43.46 kcal mol-1, respectively) values and nearly diffusion- controlled fluorescence quenching rate constants (kqTR) 0.36 × 1010 M-1 s-1 and 0.28 × 1010 M-1 s-1, respectively, from time-resolved fluorescence quenching study. The transient absorption spectra of DMN.+, DMA.+, and 1a.- are obtained initially by pulse radiolysis in order to correlate the time- resolved absorption spectral data. Laser flash photolysis studies in the nanosecond time domain have confirmed the generation of 1a.-, DMN.+, and DMA.+, supporting the participation of the triplet state of DMN or DMA in the ET reaction. Mesolytic cleavage of 1a.- produced a silyl radical and a phenyl selenide anion. The preparative PET activation of 1a in acetonitrile in the presence of DMN or DMA leads to the formation of 5 and 6, confirming the fragmentation pattern of la.-. The overall ET rate constants (kr(DMN) = 0.99 × 1010 M-1 s-1 and kr(DMA) = 1.62 × 1010 M-1 s-1) and limiting quantum yields (φlim(DMN) = 0.034 and φlim(DMA) = 0.12) are estimated from the inverse plot (1/[1a] vs 1/φdis) obtained by measuring the dependence of photodissociation quantum yields of 1a at its maximum concentration in the presence of DMN or DMA. Silicon-centered radical species generated from the mesolysis of 1a.- are utilized for initiating a radical reaction by the abstraction of halogen atom from -C-X (X = Cl, Br) bonds, while PhSe-1 terminates the radical sequences via PhSeSePh. This concept is successfully applied for the bimolecular group transfer (BMGT) radical reactions and intermolecular radical chain addition reactions.

Direct conversion of a benzylic hydroxy group into a selenenyl group using the phenyl trimethylsilyl selenide-aluminum bromide combination

A new reagent system, phenyl trimethylsilyl selenide-aluminum bromide, was developed for the direct conversion of various benzylic hydroxy groups into a selenenyl group. Treatment of cinnamyl alcohol with this reagent system yielded 3,4-dihydro-4-phenyl-2H-1-benzoselenin via a [3,3]-sigmatropic rearrangement of the intermediate cinnamyl phenyl selenide.

ORGANOSELENIUM COMPOUNDS VII. METHODS OF CONTROLLING THE REACTION OF ORGANIC HALIDES WITH MAGNESIUM AND SELENIUM

The action of aryl bromides on a mixture of magnesium and selenium in ether in ratios of 1.5-2:1:1 leads to diaryl selenides and bis(bromomagnesium) selenide, which gives organic selenides with electrophiles.The reaction of Grignard reagents with an excess of selenium (ArBr:Mg:Se ratios of 1:1:1.5) in ether leads to diaryl diselenides, while the reaction in THF leads to a mixture of polyselenides and diaryl diselenides.

BEITRAG ZUR SYNTHESE VON ORGANYL-TRIMETHYLSILYL-SELENIDEN, R-Se-Si(CH3)3

Phenyl-trimethyl-selenide and 2,4,6-trimethylphenyl-selenide have been synthesized and characterized from the organobromide, magnesium, selenium and trimethylchlorosilane.A better method has been found for the synthesis of organyl-trimethylsilyl-selenides.It starts from sodium-trimethylsilylselanolate, the synthesis of which is described.Its reactions with methylbromide, benzylbromide and n-pentylbromide result in the formation of the compounds R-Se-Si(CH3)3 with the corresponding groups R.Secundary as well as tertiary bromides do not react in the expected manner.

SYNTHESIS OF SELENOACETALS

This paper reports our results concerning the syntheses of various bis(alkylseleno)alkanes and some of their arylseleno analogues by different methods.The scope and limitation of each of them are presented.

Substitution Reactions of Thallous Thiophenoxide and Thallous Phenylselenide with Halogen-Bearing Substrates

Thallous thiophenoxide (1) and thallous selenide (2) were prepared by the action of either thallous ethoxide or thallous pentoxide on thiophenol and benzeneselenol.The reagents 1 and 2 reacted readily with aroyl and acyl halides, imidoyl chlorides, α-halo ketones, α-halo esters, α-halo lactones, α-halo carboxylic acids, allyl halides, alkyl halides, chlorotrimethylsilane, chloroacetonitrile, and N-chlorosuccinimide to give substitution products and varying amounts of diphenyl disulfide and diphenyl diselenide.The reactions were run as heterogeneous mixtures in ether.The origin of the diphenyl disulfide and diphenyl diselenide was homolytic cleavage of the thallium-sulfur or thallium-selenium bond, on the basis of the products derived from the reactions of N-chlorosuccinimide with 1 and 2.