312-40-3

Basic information

• Product Name: DIPHENYLDIFLUOROSILANE
• Synonyms: DIPHENYLDIFLUOROSILANE;Diphenyl difluorosilanegas cylinder;DIFLUORODIPHENYLSILANE;difluorodiphenyl-silan;Diphenylsilane difluoride;Difluorodiphenylsilane97%;Benzene,1,1'-(difluorosilylene)bis-
• CAS NO: 312-40-3
• Molecular Formula: C₁₂H₁₀F₂Si
• Molecular Weight: 220.29
• EINECS: 206-226-8
• Mol File: 312-40-3.mol
• Article Data: 23

Chemical Properties

• Boiling Point: 159°C 50mm
• Flash Point: 87°C
• Appearance: /
• Density: 1.145
• Vapor Pressure: 0.0315mmHg at 25°C
• Refractive Index: 1.522
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: soluble in ether.
• CAS DataBase Reference: DIPHENYLDIFLUOROSILANE(CAS DataBase Reference)
• NIST Chemistry Reference: DIPHENYLDIFLUOROSILANE(312-40-3)
• EPA Substance Registry System: DIPHENYLDIFLUOROSILANE(312-40-3)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: 1760
• TSCA: Yes
• Hazardous Substances Data: 312-40-3(Hazardous Substances Data)

Usage

Physical properties

bp 246–247 °C, bp 156°C50 mmHg, bp 66–70°C0.5 mmHg; d 1.155 g cm?1.

Uses

A moisture insensitive equivalent of diphenyldichlorosilane that is more reactive toward nucleophiles. Source of phenyl group in the Hiyama coupling reaction. More stable to electrophilic aromatic substitution than diphenyldichlorosilane. Eaborn reported that fluorosilanes are more reactive toward organometallic reagents than the corresponding chlorosilanes, and therefore more suited for preparation of sterically hindered organosilanes.

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

• 128499-30-9 chloromethyl(p-methoxyphenyl)diphenylsilane 
• 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 
• 485325-13-1 [3-(benzyloxy)-1,1-dimethylpropoxy]diphenyl-{[(E)-3-phenyl-2-propenyl]oxy}silane 
• 485325-15-3 (1R,2S,5R)-(3-benzyloxy-1,1-dimethylpropoxy)-(2-isopropyl-4-methylcyclohexyloxy)diphenylsilane 
• 7783-61-1 silicon tetrafluoride 
• 485817-98-9 [Rh(F)(PEt₃)₃] 
• 754-12-1 2,3,3,3-tetrafluoro-propene 
• 379-50-0 triphenylsilyl fluoride 
• 27607-80-3 Diphenylsilicium-bis(trifluormethansulfonat) 
• 7783-56-4 antimony(III) fluoride 

Downstream Products

• 68260-14-0 (diphenyl)fluorosilane 
• 35937-05-4 4-[(4-hydroxyphenyl)diphenylsilyl]phenol 
• 92-52-4 biphenyl 
• 66583-27-5 2,2-diphenyl-6-methyl-1,3-dioxa-6-aza-2-silacyclooctane 
• 66586-09-2 1,1-diphenyl-5-methylquasisilatrane 
• 1531588-55-2 1,1-diphenyldipyridinosilole 
• 92-91-1 biphenyl-4-acetaldehyde 
• 644-08-6 4-Methylbiphenyl 
• 62978-24-9 1-(Fluoro-diphenyl-silanyl)-2,2,4,4,6,6-hexamethyl-[1,3,5,2,4,6]triazatrisilinane 
• 57915-51-2 1-Fluoro-2,3,3,3-tetramethyl-1,1-diphenyl-disilazane 
• 67091-96-7 1,3-Bis-(fluoro-diphenyl-silanyl)-2,2,4,4,6,6-hexamethyl-[1,3,5,2,4,6]triazatrisilinane 
• 65768-29-8 N-(Fluordiphenylsilyl)-isopropylamin 
• 60556-32-3 N-(Fluordiphenylsilyl)-tert-butylamin 
• 72508-86-2 C₁₈H₂₈FNOSi₃ 

Relevant articles and documents

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.

Unusual reaction of trifluorophenylsilane with dimethyl sulfoxide

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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.

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.