6689-22-1

Basic information

• Product Name: 1,3-DIPHENYL-1,3-DIMETHYLDISILOXANE
• Synonyms: 1,3-DIPHENYL-1,3-DIMETHYLDISILOXANE;DIMETHYL-DIPHENYLSILOXANE;Diphenyldimethyldisiloxane;1,3-Dimethyl-1,3-diphenylpropanedisiloxane;1,3-Diphenyl-1,3-dimethylpropanedisiloxane;2,4-Diphenyl-3-oxa-2,4-disilapentane
• CAS NO: 6689-22-1
• Molecular Formula: C₁₄H₁₈OSi₂
• Molecular Weight: 258.46
• Mol File: 6689-22-1.mol

Chemical Properties

• Boiling Point: 120℃ (2 torr)
• Appearance: /
• Density: 1.09
• Refractive Index: 1.5282
• CAS DataBase Reference: 1,3-DIPHENYL-1,3-DIMETHYLDISILOXANE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-DIPHENYL-1,3-DIMETHYLDISILOXANE(6689-22-1)
• EPA Substance Registry System: 1,3-DIPHENYL-1,3-DIMETHYLDISILOXANE(6689-22-1)

Safety Data

• Hazardous Substances Data: 6689-22-1(Hazardous Substances Data)

Usage

Uses

Used in Silicone Synthesis:
1,3-Diphenyl-1,3-dimethyldisiloxane is used as a crosslinker in the synthesis of silicones, which are extensively utilized in a range of industrial and consumer applications. These applications include the production of adhesives, sealants, and lubricants, where the compound's ability to form stable crosslinks contributes to the end products' performance and durability.
Used in Polymer Production:
As a building block in the production of polymers, 1,3-diphenyl-1,3-dimethyldisiloxane helps create materials with specific properties tailored for various uses. These properties can include heat and chemical resistance, electrical insulation, and water repellency, making the resulting polymers suitable for specialized applications in industries such as electronics, automotive, and construction.
Used as a Coupling Agent in Organic Synthesis:
1,3-Diphenyl-1,3-dimethyldisiloxane also functions as a coupling agent in organic synthesis, facilitating the formation of desired products by connecting different molecular fragments. Its stability and reactivity make it an effective component in this role, enhancing the efficiency and selectivity of the synthesis process.
Used as a Protective Group in Organic Reactions:
In addition to its other uses, 1,3-diphenyl-1,3-dimethyldisiloxane serves as a protective group in organic reactions. This function allows chemists to temporarily mask specific functional groups during a reaction, preventing unwanted side reactions and ensuring the desired product is formed. The protective group can then be removed under mild conditions once the reaction is complete, revealing the intended product with the original functional group intact.

Upstream product

• 1631-82-9 chloro(methyl)phenylsilane 
• 109-72-8 n-butyllithium 
• 64-17-5 ethanol 
• 766-08-5 methylphenylsilane 
• 7427-12-5 methyl-naphthalen-1-yl-phenyl-silane 
• 1825-14-5 pentane-1,3-diol 
• 615-41-8 2-iodochlorobenzene 
• 70996-44-0 (2-phenylpropan-2-ylperoxy)methyl(phenyl)silane 
• 2935-44-6 hexane-2,5-diol 
• 917-64-6 methyl magnesium iodide 
• 41422-91-7 Ph(1-Np)SiHCl 

Downstream Products

• 13222-44-1 1,3-bis-[3-(2,3-epoxy-propoxy)-propyl]-1,3-dimethyl-1,3-diphenyl-disiloxane 
• 129073-86-5 1,3-dimethoxy-1,3-dimethyl-1,3-diphenylsiloxane 
• 85028-94-0 cis-[trans-1,3-diphenyl-1,3-dimethyldisiloxanediyl]bis(triphenylphosphine)platinum(II) 
• 142414-24-2 [3-(1,3-Dimethyl-1,3-diphenyl-disiloxanyl)-propyl]-dimethyl-amine 

Relevant articles and documents

Catalytic oxidation of diorganosilanes to 1,1,3,3-tetraorganodisiloxanes with gold nanoparticle assembly at the water-chloroform interface

The formation of the spherical self-assembly of gold nanoparticles (AuNPs) of 200 ± 20 nm size at the water-chloroform interface is achieved by employing the cyclotetrasiloxane [RSCH2CH2SiMeO]4 (R = CH2CH2OH) as the stabilizing ligand. The interfacially stabilized AuNPs act as a versatile catalyst for selective hydrolytic oxidation of only one of the Si-H bonds in secondary organosilanes, RR1SiH2 (R, R1 = alkyl, aryl, and sila-alkyl), to afford the high yield synthesis of 1,1,3,3-tetraorganodisiloxanes, (HRR1Si)2O. The study unravels for the first time the role of the photothermal effect arising from the excitation of the surface plasmon resonance of the AuNPs under visible light irradiation in enhancing the catalytic activity at ambient temperature.

Scalable Synthesis of Hydrido-Disiloxanes from Silanes: A One-Pot Preparation of 1,3-Diphenyldisiloxane from Phenylsilane

A simple, one-pot, and high-yielding synthesis of 1,3-diphenyldisiloxane is presented. The preparation of similar symmetrical disiloxane materials is also accomplished with this same protocol. This mechano-chemical procedure is efficient and highly scalab

An efficient and simple method for the preparation of symmetrical disiloxanes from hydrosilanes by Lewis acid-catalyzed air oxidation

Symmetrical disiloxanes were prepared in high yields by air oxidation of mono, di, and trihydrosilanes under Lewis acid catalysis.

Zinc-catalyzed nucleophilic substitution reaction of chlorosilanes with organomagnesium reagents

Zinc-catalyzed nucleophilic substitution reactions of chlo-rosilanes with organomagnesium reagents afford various tetraorganosilanes under mild reaction conditions. The reactions can be performed on large scale and allow efficient preparation of functionalized tetraorganosilanes.

Electrochemical synthesis of symmetrical difunctional disilanes as precursors for organofunctional silanes

Difunctional disilanes of the general type XR2SiSiR2X (1-5) (X = OMe, H; R = Me, Ph, H) have been synthesized by electrolysis of the appropriate chlorosilanes XR2SiCl in an undivided cell with a constant current supply and in the absence of any complexing agent. Reduction potentials of the chlorosilane starting materials derived from cyclic voltammetry measurements were used to rationalize the results of preparative electrolyses. Organofunctional silanes of the general formula MeO(Me 2)SiC6H4Y (6a-c, 7) were subsequently obtained by the reaction of sym-dimethoxytetramethyldisilane (1) with NaOMe in the presence of p-functional aryl bromides BrC6H4Y (Y = OMe, NEt2, NH2).

Redistribution of dichlorosilanes and dihydridosilanes. Synthesis of chloro hydridosilanes

The redistribution of dichlorosilanes RSi(CH3)Cl2 and dihydridosilanes RSi(CH3)H2, prepared by reduction of the homologues dichlorosilanes, in the presence of a quaternary ammonium salt is presented. The influence of the nature of R (fluoroalkyl chain RFCH2CH2 with RF = CF3, C4F9, C8F17, alkyl chain R = C6H13 or aromatic R = C6H5) and of the temperature on the rate of the reaction is studied. The equilibrium constants and free enthalpies are calculated and discussed taking into account the nature of R. The new products described were characterized from I.R, 1H, 19F and 29Si NMR spectroscopies.

Conversion of hydrosilanes to alkoxysilanes catalyzed by Cp2TiCl2/nBuLi

The combination of Cp2TiCl2 and nBuLi provides an effective catalyst for alcoholysis of the model silanes n-HexSiH3, PhMeSiH2, Ph2SiH2 and PhMe2SiH by ethanol, isopropanol, t-butyl alcohol and phenol.Increasing the steric bulk of the substituents on either the alcohol or the silane generally requires longer reaction periods and/or increasing temperature.All SiH bonds are converted to SiOEt groups by ethanol and a single SiH bond in secondary silanes and two SiH bonds in tertiary silanes are replaced by t-butyl alcohol.Diols including pinacol, 2,4-pentanediol and 2,5-hexanediol react with PhRSiH2 (R = Me, Ph) to give 1,3-dioxa-2-silacyclopentanes, -hexanes and -heptanes, respectively.Attempts to form caged structures by condensation of primary silanes and triols was unsuccessful.Hydrolysis of PhRSiH2 is promoted by Cp2TiCl2/n-BuLi and the siloxane is produced in quantitative yield when R = Ph and a mixture of linear disiloxanes and trisiloxanes in addition to cyclopolysilanes are produced when R = Me.Other protic reagents including acids, mercaptans, amines and enolizable ketones did not react.The effects of reaction parameters such as temperature, silane to catalyst ratio, solvent, transition metal and replacements for nBuLi were also determined.

THE SILICON-OXYGEN DOUBLE-BONDED INTERMEDIATES. A NEW METHOD FOR THE FORMATION OF ORGANOSILANONES

The kinetics and mechanism of thermal decomposition of R1R2(H)SiOOR3 silylperoxides have been studied.It has been shown that peroxides generated diorganosilanones, R1R2Si=O, with a high yield in the temperature range 130-180 deg C.A mechanism is suggested for the silanone formation.The interaction of silanones with cyclosiloxanes, triethylsilane, α-methylstyrene has been investigated as well as the cyclisation of silanones.

THE REARRANGEMENT OF 1-NAPHTHYLPHENYLMETHYLSILANE

1-Naphthylphenylmethylsilane has been shown to undergo rearrangement to the 2-isomer when treated with HI in benzene or ether-benzene; protodesilylation also occurs.The rearrangement also takes place when 1-naphthylphenylmethylsilane is heated at 210-220 deg C.