17920-15-9

Usage

Chemical Properties

Clear colorless liquid

Upstream product

• 17881-63-9 chlorodimethyl(4-methylphenyl)silane 
• 1432-39-9 dimethyl-p-tolylsilane 
• 17988-22-6 ethoxy(dimethyl)(p-tolyl)silane 
• 541-05-9 Hexamethylcyclotrisiloxane 
• 106-38-7 para-bromotoluene 
• 56633-16-0 1,1-dimethylphenylmethylsilanol 
• 51501-87-2 dimethyl(4-methylphenyl)methoxysilane 

Downstream Products

• 67-56-1 methanol 
• 66870-89-1 1,1,1-trimethyl-3,3-dimethyl-3-tolyldisiloxane 
• 17555-94-1 (E)-4'-methoxy-4-methylstilbene 
• 613-33-2 (4,4'-dimethyl-1,1'-biphenyl) 
• 123248-21-5 (E)-n-butyl 3-(p-tolyl)acrylate 
• 51501-87-2 dimethyl(4-methylphenyl)methoxysilane 
• 104144-48-1 C₂₂H₃₉ClO₄Si₅ 

Relevant academic research and scientific papers

METHOD OF PREPARING SILANOLS WITH SELECTIVE CYTOCHROME P450 VARIANTS AND RELATED COMPOUNDS AND COMPOSITIONS

This disclosure provides a method of preparing a silanol-functional organosilicon compound with a cytochrome P450 variant that facilitates the oxidization of a silyl hydride group to a silanol group in the presence of oxygen. The method includes combining the cytochrome P450 variant and an organosilicon compound having at least one silicon-bonded hydrogen atom to give a reaction mixture and exposing the reaction mixture to oxygen to oxidize the organosilicon compound, thereby preparing the silanol-functional organosilicon compound. Cytochrome P450 variants suitable for use in the method are also disclosed, along with methods for engineering and optimizing the same. Nucleic acids encoding the cytochrome P450 variants and compositions, expression vectors, and host cells including the same are also disclosed.

Photocatalyzed cross-dehydrogenative coupling of silanes with alcohols and water

An efficient method for the dehydrogenative coupling of silanes with alcohols under photocatalysis was developed. The reaction proceeded in the presence of Ru(bpy)3Cl2(0.5 mol%) under visible light irradiation in acetonitrile at room temperature. The developed methodology was also applicable for the synthesis of silanols using water as a coupling partner.

Selective Enzymatic Oxidation of Silanes to Silanols

Compared to the biological world's rich chemistry for functionalizing carbon, enzymatic transformations of the heavier homologue silicon are rare. We report that a wild-type cytochrome P450 monooxygenase (P450BM3 from Bacillus megaterium, CYP102A1) has promiscuous activity for oxidation of hydrosilanes to give silanols. Directed evolution was applied to enhance this non-native activity and create a highly efficient catalyst for selective silane oxidation under mild conditions with oxygen as the terminal oxidant. The evolved enzyme leaves C?H bonds present in the silane substrates untouched, and this biotransformation does not lead to disiloxane formation, a common problem in silanol syntheses. Computational studies reveal that catalysis proceeds through hydrogen atom abstraction followed by radical rebound, as observed in the native C?H hydroxylation mechanism of the P450 enzyme. This enzymatic silane oxidation extends nature's impressive catalytic repertoire.

Hydrogenation of silyl formates: sustainable production of silanol and methanol from hydrosilane and carbon dioxide

A new process for simultaneously obtaining two chemical building blocks, methanol and silanol, was realized starting from silyl formates which can be derived from silane and carbon dioxide. Understanding the reaction mechanism enabled us to improve the reaction efficiency by the addition of a small amount of methanol.

A discrete octahedrally shaped [Ag6]4+ cluster encapsulated within silicotungstate ligands

By the reaction of TBA4H4[γ-SiW 10O36] (TBA = tetra-n-butylammonium) with AgOAc (OAc = acetate) using dimethylphenylsilane as a reductant in acetone, a unique polyoxometalate containing a discrete octahedrally shaped [Ag6] 4+ cluster, TBA8[Ag6(γ-H 2SiW10O36)2]·5H2O, could be synthesized, and the molecular structure was determined.

Diamond-shaped [Ag4]4+ cluster encapsulated by silicotungstate ligands: Synthesis and catalysis of hydrolytic oxidation of silanes

An Ag4 diamond is encapsulated by silicotungstate ligands in TBA8[Ag4(DMSO)2(γ-H2SiW 10O36)2]·2 DMSO·2 H2O (Ag4; DMSO=dimethyl sulfoxide, TBA=tetra-n-butylammonium), which was obtained by reaction of TBA4H4[γ-SiW10O 36] with AgOAc in an organic medium. Polyoxometalate Ag4 (see picture) selectively catalyzes hydrolytic oxidation of various silanes to the corresponding silanols in high yields (72-96 %). Copyright

Highly selective oxidation of organosilanes to silanols with hydrogen peroxide catalyzed by a lacunary polyoxotungstate

Silanol synthesis: Divacant lacunary polyoxotungstate (nBu4N+)4[g- SiW10O34(H2O)2] (I) is an efficient homogeneous catalyst for highly selective oxidation of organosilanes to silanols with 30/60% aqueous H2O2. Various kinds of silanes 1 containing aryl, alkyl, alkenyl, alkynyl and alkoxy groups are chemoselectively converted into the corresponding silanols 2 in high yields with only one equivalent of aqueous H2O2 with respect to the substrate.

Supported gold nanoparticle catalyst for the selective oxidation of silanes to silanols in water

Hydroxyapatite-supported gold nanoparticles (AuHAP) can act as highly efficient and reusable catalysts for the oxidation of diverse silanes into silanols in water; this is the first catalytic methodology for the selective synthesis of aliphatic silanols using water under organic-solvent-free conditions.

Supported silver-nanoparticle-catalyzed highly efficient aqueous oxidation of phenylsilanes to silanols

Bon Apatite! Hydroxyapatite-supported silver nanoparticles act as a highly efficient heterogeneous catalyst for the oxidation of diverse phenylsilanes into silanols in water (see picture; C orange, H red, O blue, R purple, Si green), while suppressing significant condensation to the disiloxanes. The solid silver catalyst is readily reusable without any loss of activity or selectivity. (Figure Presented)

Palladium-Catalyzed Silylation of Aryl Bromides Leading to Functionalized Aryldimethylsilanols

Equation presented. A mild and general palladium-catalyzed insertion of 1,2-diethoxy-1,1,2,2-tetramethyldisilane into a variety of aryl bromides affords the aryldimethylsilyl ethers in high yields. Hydrolysis of the ethers under pH-optimized conditions results in the exclusive formation of the desired aryldimethylsilanols.