312-40-3

Usage

Uses

Used in Chemical Synthesis:
DIPHENYLDIFLUOROSILANE is used as a reagent in the Hiyama coupling reaction for introducing phenyl groups. Its higher reactivity towards nucleophiles makes it a preferred choice over diphenyldichlorosilane.
Used in Organosilane Preparation:
In the field of organosilane synthesis, DIPHENYLDIFLUOROSILANE is used as a precursor for sterically hindered organosilanes. Its increased reactivity towards organometallic reagents, as reported by Eaborn, makes it more effective in the preparation of these compounds.
Used in Material Science:
Due to its stability against electrophilic aromatic substitution, DIPHENYLDIFLUOROSILANE can be used in the development of new materials with enhanced properties, such as improved resistance to chemical reactions or increased thermal stability.
Used in Pharmaceutical Industry:
DIPHENYLDIFLUOROSILANE may also find applications in the pharmaceutical industry, potentially as a building block for the synthesis of novel drug molecules or as a component in drug delivery systems, taking advantage of its unique reactivity and stability properties.

Preparation

commercially available. Readily prepared by oxidation of diphenylsilane with CuF2, or by treatment of diphenyldichlorosilane with HF, ZnF2, NaBF4, or (NH4)2SiF6. Rate enhancements of the chlorine–fluorine exchange have been achieved with ultrasound and addition of water. Diethoxydiphenylsilane and related structures are converted to diphenyldifluorosilane with 48% HF(aq).

InChI:InChI=1/C12H10F2Si/c13-15(14,11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10H

Upstream product

• 80-10-4 diphenylsilyl dichloride 
• 17067-65-1 (chloromethyl)triphenylsilane 
• 128499-29-6 chloromethyl(p-methylphenyl)diphenylsilane 
• 128499-28-5 chloromethyl(p-chlorophenyl)diphenylsilane 
• 128499-31-0 (chloromethyl)[4-(dimethylamino)phenyl]diphenylsilane 
• 128499-27-4 (chloromethyl)diphenyl(p-trifluoromethylphenyl)silane 
• 85465-19-6 1,1,1,2-Tetrachloro-2,2-diphenyl-disilane 
• 138914-12-2 1-(Difluoro-phenyl-silanyl)-2-(fluoro-diphenyl-silanyl)-benzene 
• 546-56-5 octaphenylcyclotetrasiloxane 
• 512-63-0 1,1,3,3,5,5-hexaphenylcyclotrisiloxane 
• 368-47-8 phenyltrifluorosilane 
• 67-68-5 dimethyl sulfoxide 
• 68-12-2 N,N-dimethyl-formamide 
• 27871-49-4 (S)-Methyl lactate 

Downstream Products

• 2553-19-7 diethoxydiphenylsilane 
• 68260-14-0 (diphenyl)fluorosilane 
• 72508-86-2 C₁₈H₂₈FNOSi₃ 
• 92-91-1 biphenyl-4-acetaldehyde 
• 644-08-6 4-Methylbiphenyl 
• 86-00-0 2-nitrobiphenyl 
• 137935-69-4 Di-tert-butylfluorsilyl(fluordiphenylsilyl)amin 
• 35937-05-4 4-[(4-hydroxyphenyl)diphenylsilyl]phenol 
• 92-52-4 biphenyl 
• 202743-26-8 3-butenyl(fluoro)diphenylsilane 
• 727726-30-9 [2-(phenylmethyl)-1,3-dithian-2-yl]fluorodiphenylsilane 
• 66583-27-5 2,2-diphenyl-6-methyl-1,3-dioxa-6-aza-2-silacyclooctane 
• 137935-79-6 Di-tert-butylfluorsilyl(difluormethylsilyl)(fluordiphenylsilyl)amin 
• 66586-09-2 1,1-diphenyl-5-methylquasisilatrane 

Relevant academic research and scientific papers

Isolable Silicon-Based Polycations with Lewis Superacidity

Molecular silicon polycations of the types R2Si2+ and RSi3+ (R=H, organic groups) are elusive Lewis superacids and currently unknown in the condensed phase. Here, we report the synthesis of a series of isolable terpyridine-stabilized R2Si2+ and RSi3+ complexes, [R2Si(terpy)]2+ (R=Ph 12+; R2=C12H8 22+, (CH2)3 32+) and [RSi(terpy)]3+ (R=Ph 43+, cyclohexyl 53+, m-xylyl 63+), in form of their triflate salts. The stabilization of the latter is achieved through higher coordination and to the expense of reduced fluoride-ion affinities, but a significant level of Lewis superacidity is nonetheless retained as verified by theory and experiment. The complexes activate C(sp3)?F bonds, as showcased by stoichiometric fluoride abstraction from 1-fluoroadamantane (AdF) and the catalytic hydrodefluorination of AdF. The formation of the crystalline adducts [2(F)]+ and [5(H)]2+ documents in particular the high reactivity towards fluoride and hydride donors.

Nucleophilic fluorination of alkoxysilane with alkali metal hexafluorophosphate 1 - part 1

Alkali metal hexafluorophosphates were used to effect nucleophilic fluorination of a few selected alkoxysilanes both in the presence and absence of polar solvents. Near-quantitative yields of fluorinated silanes were obtained using both alkoxy-equivalent of the complex salt and fluoride equivalents of alkoxysilanes. Some of the intermediate fluorosilanes and fluorophosphorus compounds were identified and the mechanism of fluorination is proposed.

METHOD FOR MANUFACTURING SILSESQUIOXANE COMPOUND

Provided is a method for manufacturing a silsesquioxane compound represented by general formula (III) shown below, the method having a step of reacting a compound represented by general formula (I) shown below and a compound represented by general formula (II) shown below. In general formulas (I) to (III): each of R1 and R2 independently represents a hydrogen atom, an alkyl group of 1 to 8 carbon atoms, an aryl group of 6 to 14 carbon atoms, an aminoalkyl group, an amino group-containing group, a nitrile group-containing group, a vinyl group-containing group, a (meth)acryloyl group-containing group, a chloro group-containing group, a bromo group-containing group, or a functional group containing a boron trifluoride-complexed amino group, each of R3 to R10 independently represents an alkyl group of 1 to 8 carbon atoms or an aryl group of 6 to 14 carbon atoms, and M represents at least one element selected from the group consisting of hydrogen, lithium, sodium and potassium.

Synthesis method of diphenyl difluorosilane

The invention discloses a synthesis method of diphenyl difluorosilane, belonging to the technical field of additives for battery electrolytes. The synthesis method comprises the following steps: withphenyldiethoxysilane as a raw material, adding phenyldiethoxysilane into a dry container; carrying out heating to 80-100 DEG C, and adding sodium trichloropyridinol and ethanol while stirring; then dropwise adding chlorobenzene into a mixture obtained in the previous step; after dropwise adding is finished, carrying out a reflux reaction for 3-8 hours, and conducting cooling to 30-35 DEG C; carrying out reduced-pressure suction filtration, adding sodium tetrafluoroborate into a filtrate, performing heating to 180-220 DEG C, and carrying out reacting for 4-6 hours; then conducting cooling to room temperature, performing diluting with dichloromethane, conducting quenching with water, and separating out an organic layer; and carrying out drying, carrying out vacuum concentration, and carryingout reduced-pressure distillation to obtain diphenyl difluorosilane. The synthesis method is simple, raw materials are cheap and easily available, reaction is stable, yield is high, and purity is high.

Synthesis of Double-Decker Silsesquioxanes from Substituted Difluorosilane

A novel synthetic method for the construction of a double-decker silsesquioxane from fluorosilanes was developed. Phenyl-substituted double-decker silsesquioxane was prepared under mild conditions by coupling difluorodiphenylsilane and a tetrasiloxanolate precursor. A similar reaction was performed using difluorovinylsilane, and a divinyl double-decker silsesquioxane was obtained. The one-step reaction of a functional difluorosilane containing an aminopropyl group afforded a novel double-decker silsesquioxane with two amino groups complexed with BF3, which can react with carboxylic acid anhydrides to afford an amide product. This synthetic method using difluorosilane is tolerant of a wide range of functional groups and is applicable to the synthesis of polycyclic silsesquioxanes bearing amino groups, which are difficult to directly obtain from dichlorosilane.

C?H and C?F Bond Activation Reactions of Fluorinated Propenes at Rhodium: Distinctive Reactivity of the Refrigerant HFO-1234yf

The reaction of [Rh(H)(PEt3)3] (1) with the refrigerant HFO-1234yf (2,3,3,3-tetrafluoropropene) affords an efficient route to obtain [Rh(F)(PEt3)3] (3) by C?F bond activation. Catalytic hydrodefluorinations were achieved in the presence of the silane HSiPh3. In the presence of a fluorosilane, 3 provides a C?H bond activation followed by a 1,2-fluorine shift to produce [Rh{(E)-C(CF3)=CHF}(PEt3)3] (4). Similar rearrangements of HFO-1234yf were observed at [Rh(E)(PEt3)3] [E=Bpin (6), C7D7 (8), Me (9)]. The ability to favor C?H bond activation using 3 and fluorosilane is also demonstrated with 3,3,3-trifluoropropene. Studies are supported by DFT calculations.

Synthesis and kinetics of disassembly for silyl-containing ethoxycarbonyls using fluoride ions

In this study, a series of silyl-containing ethoxycarbonates and ethoxycarbamates on electron poor anilines and phenols were synthesized and their kinetics of disassembly determined in real-time upon exposure to fluoride ion sources at room temperature. The results provide a greater understanding of stability and kinetics for silyl-containing protecting groups that eliminate volatile molecules upon removal, which will allow for simplification of orthogonal protection in complex organic molecules.

Synthesis and applications of tert-alkoxysiloxane linkers in solid-phase chemistry

Straightforward syntheses of two tert-alkoxysilyl chloride functionalised resins 3 and 31 that allow facile attachment of 1°, 2°, 3° alcohols and phenols to the solid-phase have been achieved. Resin 3 displayed useful loading levels (0.7 mmol/g), and it was stable to storage in activated form. Siloxanes from reaction of 3 with alcohols and phenols were compatible with a variety of reaction conditions commonly used in solid-phase synthesis.

Reaction of germanium tetrachloride with chloro(phenyl)silanes in the presence of aluminum chloride

The effect of the quantity of aluminum chloride on the direction and depth of reaction of germanium tetrachloride with chloro(phenyl)silanes of the general formula PhnSiCl4-n (n = 1 - 3) was studied to show that radical exchange between germanium and silicon is initiated only if the mixture contains no less than 2.5-5 wt % of aluminum chloride. With trichloro(phenyl)silane, the radical exchange is initiated at 5 wt % of aluminum chloride and results in exclusive formation of trichloro(phenyl)germane. The reactions of GeCl4 with dichlorodiphenylsilane and chlorotriphenylsilane in the presence of 2.5-7.5 wt % of aluminum chloride give dichlorodiphenylgermane as the major product, and at AlCl3 concentrations of above 10 wt % the major product becomes to be trichloro(phenyl)germane.

Electronic effects and the stereochemistries in rearrangement-displacement reactions of triaryl(halomethyl)silanes with fluoride and with alkoxide ions

Tetrabutylammonium fluoride (TBAF) reacts with (halomethyl)diphenyl(para-substituted-phenyl)silanes (13, X = Cl), 14 (X = Br), and 15 (X = I) in ether solvents to give fluorodiphenyl(parasubstituted-phenylmethyl)silanes (17a) and fluorophenyl(phenylmethyl)(para-substituted-phenyl)silanes (20a) by attack on silicon and migrations of the phenyl or the para-substituted-phenyl groups to C-1 with displacement of chloride ion. Sodium methoxide in dioxane effects rearrangement displacements of 14 (X = Br) to yield methoxydiphenyl(para-substituted-phenylmethyl)silanes (17b) and methoxyphenyl(phenylmethyl)(para-substituted-phenyl)silanes (20b). The migratory aptitudes of the varied phenyl groups in rearrangement-displacements of 13 with F- at 25°C are p-CF3-Ph, 2.72 > p-Cl-Ph, 1.67 > Ph, 1.00 > p-CH3-Ph, 0.91 > p-CH3O-Ph, 0.58 > p-(CH3)2N-Ph, 0.55. For reactions of 14 with sodium methoxide in dioxane, the migratory aptitudes at 23°C are p-CF3-Ph, 2.53 > p-Cl-Ph, 1.64 > Ph, 1.00 > p-CH3O-Ph, 0.84 > p-CH5-Ph, 0.79 > p-(CH3)2N-Ph, 0.68. The migratory aptitudes in the above rearrangement-displacements are increased by electron withdrawing substituents, and logarithms of the migratory aptitudes give satisfactory linear correlations with σ and/or σ-zero values of the phenyl substituents. Hammett correlations however of the migratory aptitudes from reactions of F- with 13 (X = Cl) at 0 and -20°C, 14 (X = Br) at 23, 0, and -20°C, and 15 (X = I) at 23°C are not linear. (+)-(Bromomethyl)methyl-1 naphthylphenylsilane (23, [α]D23 +8.29°, cyclohexane) reacts with CsF and with TBAF in THF to give benzylfluoromethyl-1-naphthylsilane (51, [α]D25 = 0.00°, cyclohexane) and fluoromethyl-(1 naphthylmethyl)phenylsilane (52, impure) in 10.4:1 ratio along with unchanged 23 ([α]D23 8.29°, cyclohexane). Sodium methoxide and (+)-23 in dioxane at 25°C and at 0°C yield (+)benzylmethoxymethyl-1-naphthylsilane (64) and (+)-methoxymethyl(1-naphthylmethyl)phenylsilane (65) in ～9:1 ratio. The conversions of (+)-23 to (+)-64 occur with 93% inversion about silicon. Reaction of (+)-23 with sodium methoxide at 25°C to give (+)-65 also occurs with inversion. Further, sodium ethoxide and sodium 2-propoxide react with (+)-23 at 20-25°C by rearrangement displacements on silicon with phenyl migrations to yield (+)-benzylethoxymethyl-1-naphthylsilane (69) and (+)-benzylmethyl-1-naphthyl-2-propoxysilane (70), respectively, each with 95% inversion about silicon. The mechanisms of rearrangement-displacements of 13-15 and (+)-23 by fluoride and by alkoxide ions are discussed.