2488-01-9

Basic information

• Product Name: 1,4-Bis(dimethylsilyl)benzene
• Synonyms: 1,4-phenylenebis(dimethyl-silan;p-Bis(dimethysilyl)benzene;p-phenylenebis(dimethyl-silan;Silane, 1,4-phenylenebis[dimethyl-;Silane, p-phenylenebis(dimethyl-;1,4-BIS(DIMETHYLSILYL)BENZENE;1,4 BIS(DIMETHYLSILYL)BENZENE MIN;1,4-phenylenebis[dimethylsilane]
• CAS NO: 2488-01-9
• Molecular Formula: C₁₀H₁₈Si₂
• Molecular Weight: 194.42
• EINECS: 219-638-8
• Mol File: 2488-01-9.mol
• Article Data: 9

Chemical Properties

• Melting Point: 115 °C
• Boiling Point: 213-214 °C(lit.)
• Flash Point: 185 °F
• Appearance: /
• Density: 0.874 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.502(lit.)
• Storage Temp.: Inert atmosphere,Room Temperature
• BRN: 1072658
• CAS DataBase Reference: 1,4-Bis(dimethylsilyl)benzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-Bis(dimethylsilyl)benzene(2488-01-9)
• EPA Substance Registry System: 1,4-Bis(dimethylsilyl)benzene(2488-01-9)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 26-36/37/39-36/37-23
• RIDADR: 1993
• WGK Germany: 3
• RTECS: VV4830000
• TSCA: Yes
• Hazardous Substances Data: 2488-01-9(Hazardous Substances Data)

Usage

General Description

1,4-Bis(dimethylsilyl)benzene is a chemical compound with the molecular formula C14H22Si2. It is a member of the organosilicon compound class and consists of a benzene ring with two dimethylsilyl groups attached to the 1 and 4 positions. 1,4-Bis(dimethylsilyl)benzene is commonly used as a precursor in the synthesis of various organic and organometallic compounds. It is also used in the production of polymers and as a building block for the construction of complex organic molecules. 1,4-Bis(dimethylsilyl)benzene is known for its stability and compatibility with a wide range of reaction conditions, making it a versatile and useful building block in organic chemistry.

InChI:InChI=1/C10H16Si2/c1-11(2)9-5-7-10(8-6-9)12(3)4/h5-8H,1-4H3

Synthetic route

dimethylmonochlorosilane (1066-35-9) + 1.4-dibromobenzene (106-37-6) → 1,4-bis(dimethylsilyl)benzene (2488-01-9)

Conditions	Yield
With magnesium In tetrahydrofuran at 50 - 85℃; for 16h; Inert atmosphere;	98%
Stage #1: 1.4-dibromobenzene With magnesium In tetrahydrofuran Inert atmosphere; Stage #2: dimethylmonochlorosilane In tetrahydrofuran at 50 - 85℃;	98%
With magnesium In tetrahydrofuran for 3h; Heating;	85%

dimethylmonochlorosilane (1066-35-9) + para-dichlorobenzene (106-46-7) → 1,4-bis(dimethylsilyl)benzene (2488-01-9)

Conditions	Yield
With Tris(3,6-dioxaheptyl)amine; sodium In 5,5-dimethyl-1,3-cyclohexadiene at 100 - 110℃; for 7h; Concentration;	95%
With magnesium In diethyl ether; toluene	86.6%

1,4-bis(dimethylsilyl)benzene (2488-01-9) → 1,4-bis(hydroxydimethylsilyl)benzene (2754-32-7)

Conditions	Yield
With oxygen In tetrahydrofuran; water at 20℃; under 760.051 Torr; for 1h; Green chemistry;	99%
With C20H24MnN8O2(2+)*2ClO4(1-)*2H2O; dihydrogen peroxide In acetone at 20℃; for 0.25h; Green chemistry;	98%
With water In tetrahydrofuran at 20℃; for 3h;	96%

1,4-bis(dimethylsilyl)benzene (2488-01-9) + phenylacetylene (536-74-3) → C18H24Si2

Conditions	Yield
With C34H39N3O2Rh(1+)*BF4(1-) In dichloromethane-d2 at 60℃; for 4h; Inert atmosphere; Glovebox; stereoselective reaction;	99%
With [Pt(1,3-bis{2,6-bis(diphenylmethyl)-4-methoxyphenyl}imidazol-2-ylidene)(divinyltetramethyldisiloxane)] In toluene at 35℃; Inert atmosphere; Schlenk technique;	92%

Allyl glycidyl ether (106-92-3) + 1,4-bis(dimethylsilyl)benzene (2488-01-9) → 1,4-bis(dimethyl(3-(oxiran-2-ylmethoxy)propyl)silyl)benzene (18715-54-3)

Conditions	Yield
With platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex In 5,5-dimethyl-1,3-cyclohexadiene at 0 - 20℃; for 1.16667h; Inert atmosphere;	97%

1,4-bis(dimethylsilyl)benzene (2488-01-9) + 1-hexene (592-41-6) → C22H42Si2

Conditions	Yield
With platinum on carbon nanotubes In neat (no solvent) at 20℃; for 36h;	97%

1,4-bis(dimethylsilyl)benzene (2488-01-9) + tris(pentafluorophenyl)borate (1109-15-5) + pentaphenylcyclopentaphosphane (3376-52-1) → C6H4(Si(CH3)2PH(C6H5)B(C6F5)3)2

Conditions	Yield
In dichloromethane	96%
In dichloromethane B(C6F5)3 added to soln. of P5Ph5, C6H4(SiMe2H)2 added, mixt. stirred overnight; elem. anal.;	96%

1,4-bis(dimethylsilyl)benzene (2488-01-9) → 1,4-bis(dimethylchlorosilyl)benzene (1078-97-3)

Conditions	Yield
With tellurium tetrachloride In benzene for 2h; Heating;	95%
With iron(III) chloride; acetyl chloride In 1,2-dichloro-ethane at 20℃; Cooling with ice;	90%
at 0℃;	64%
With trichloroisocyanuric acid In tetrahydrofuran at -20℃; Inert atmosphere; Schlenk technique;	61%
With dichloromethane; eosin y at 20℃; for 24h; Reagent/catalyst; Sealed tube; Inert atmosphere; Irradiation; Green chemistry;	99 %Spectr.

1,4-bis(dimethylsilyl)benzene (2488-01-9) + diethyl ether (60-29-7) → Reaxys ID: 11382155

Conditions	Yield
tris(pentafluorophenyl)borate In toluene at 25 - 32℃; for 4h;	95%

1,4-bis(dimethylsilyl)benzene (2488-01-9) + allylsuccinic anhydride (7539-12-0) → C4H4O3*C24H34O6Si2

Conditions	Yield
Stage #1: 1,4-bis(dimethylsilyl)benzene; allylsuccinic anhydride With dihydrogen hexachloroplatinate In ethanol; toluene at 70℃; Stage #2: 1,4-bis(dimethylsilyl)benzene In ethanol; toluene at 70 - 90℃; for 3.33333h;	95%

1,4-bis(dimethylsilyl)benzene (2488-01-9) + tris(dimethylvinylsiloxy)hepta(isobutyl)silsesquioxane (544692-95-7) → C70H144O12Si16

Conditions	Yield
With platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex In toluene at 95℃; regioselective reaction;	95%

1,4-bis(dimethylsilyl)benzene (2488-01-9) + C54H62O12Si10 → C84H116O12Si16

Conditions	Yield
With platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex In toluene at 95℃; regioselective reaction;	95%

1,4-bis(dimethylsilyl)benzene (2488-01-9) + Dimethylallene (598-25-4) → 1,4-bis(dimethyl(3-methylbut-1-en-2-yl)silyl)benzene

Conditions	Yield
With (2-diphenylphosphinocyclopentene-1-(tert-butyl)imine)(allyl)palladium(II) triflate In chloroform-d1 at 20℃; for 2h; Glovebox; Inert atmosphere; regiospecific reaction;	94%

1,4-bis(dimethylsilyl)benzene (2488-01-9) + 1-Heptyne (628-71-7) → C24H42Si2

Conditions	Yield
With [Pt(1,3-bis{2,6-bis(diphenylmethyl)-4-methoxyphenyl}imidazol-2-ylidene)(divinyltetramethyldisiloxane)] In toluene at 35℃; for 24h; Inert atmosphere; Schlenk technique;	94%

1,4-bis(dimethylsilyl)benzene (2488-01-9) + 1-ethynyl-3-methyl-benzene (766-82-5) → C28H34Si2

Conditions	Yield
With [Pt(1,3-bis{2,6-bis(diphenylmethyl)-4-methoxyphenyl}imidazol-2-ylidene)(divinyltetramethyldisiloxane)] In toluene at 35℃; for 24h; Inert atmosphere; Schlenk technique;	94%

1,4-bis(dimethylsilyl)benzene (2488-01-9) + dimethyldimethoxysilan (1112-39-6) → polymer, Mw 49.1 KDa, Mw/Mn 2.24; monomer(s): 1,4-bis(dimethylsilyl)benzene; dimethyldimethoxysilane

Conditions	Yield
With tris(pentafluorophenyl)borate In toluene	92%

1,4-bis(dimethylsilyl)benzene (2488-01-9) + N,N-bis(trimethylsilyl)allylamine (7688-51-9) → 1,4-bis(3-aminopropyldimethylsilyl)benzene (20152-18-5)

Conditions	Yield
In methanol; 5,5-dimethyl-1,3-cyclohexadiene	92%

1,4-bis(dimethylsilyl)benzene (2488-01-9) + 1-ethynyldimethylsiloxy-3,5,7,9,11,13,15-hepta(ethyl)pentacyclo[9.5.1.13,9.15,15.17,13]octasiloxane → C46H102O26Si20

Conditions	Yield
With platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex In toluene at 20℃; for 20h; Inert atmosphere; regioselective reaction;	92%

1,4-bis(dimethylsilyl)benzene (2488-01-9) + phenylacetylene (536-74-3) → 1,4-bis{((E)-2-phenylethenyl)dimethylsilyl}benzene

Conditions	Yield
With [Pt(1,3-bis{2,6-bis(diphenylmethyl)-4-methoxyphenyl}imidazol-2-ylidene)(divinyltetramethyldisiloxane)] In toluene at 35℃; for 24h; Inert atmosphere; Schlenk technique;	92%

1,4-bis(dimethylsilyl)benzene (2488-01-9) + 1-ethynyldimethylsiloxy-3,5,7,9,11,13,15-hepta(cyclohexyl)pentacyclo[9.5.1.13,9.15,15.17,13]octasiloxane → C102H186O26Si20

Conditions	Yield
With platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex In toluene at 20℃; for 20h; Inert atmosphere; regioselective reaction;	91%

1,4-bis(dimethylsilyl)benzene (2488-01-9) + phenylacetylene (536-74-3) → 1,4-bis[dimethyl(phenylethynyl)silyl]benzene (1422469-27-9)

Conditions	Yield
With pyridine; zinc trifluoromethanesulfonate; propiononitrile at 100℃; for 30h; Schlenk technique; Inert atmosphere;	90%

1,4-bis(dimethylsilyl)benzene (2488-01-9) + 2-(4-vinyl-benzyloxymethyl)-oxirane (113538-80-0) → 1,4-bis(dimethyl(4-((oxiran-2-ylmethoxy)methyl)phenethyl)silyl)benzene

Conditions	Yield
With platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex In 5,5-dimethyl-1,3-cyclohexadiene at 0 - 20℃; for 3.16667h; Inert atmosphere;	90%

1,4-bis(dimethylsilyl)benzene (2488-01-9) + cyclohexylallene (5664-17-5) → 1,4-bis((3-cyclohexylprop-1-en-2-yl)dimethylsilyl)benzene

Conditions	Yield
With (2-diphenylphosphinocyclopentene-1-(tert-butyl)imine)(allyl)palladium(II) triflate In chloroform-d1 at 20℃; for 1h; Glovebox; Inert atmosphere; regiospecific reaction;	89%

1,4-bis(dimethylsilyl)benzene (2488-01-9) + 1-ethynyldimethylsiloxy-3,5,7,9,11,13,15-hepta(isobutyl)pentacyclo[9.5.1.13,9.15,15.17,13]octasiloxane → C74H158O26Si20

Conditions	Yield
With platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex In toluene at 20℃; for 20h; Inert atmosphere; regioselective reaction;	89%

1,4-bis(dimethylsilyl)benzene (2488-01-9) + [Pt3H(PEt3)3(μ-PPh2)3] → [Pt3(SiMe2C6H4SiMe2H)(PEt3)2(μ-PPh2)3]

Conditions	Yield
In toluene byproducts: H2; under Ar or N2 atm. using Schlenk techniques; to soln. of Pt cluster in toluene added 1,4-bis(dimethylsilyl)benzene at room temp.; mixt. stirredat room temp.; solvent removed (vac.); residue washed (hexane, -70°C); dried (vac.); elem. anal.;	87%

1,4-bis(dimethylsilyl)benzene (2488-01-9) + phenylphosphane (638-21-1) → C32H42P2Si4

Conditions	Yield
With tris(pentafluorophenyl)borate In benzene at 100℃; for 36h; Kinetics; Inert atmosphere; Schlenk technique; Glovebox;	85%

1,4-bis(dimethylsilyl)benzene (2488-01-9) + trimethylsilylacetylene (1066-54-2) → 1,4-bis(dimethyl(1-(trimethylsilyl)vinyl)silyl)benzene

Conditions	Yield
With cyclopentadienylruthenium(II) trisacetonitrile hexafluorophosphate In dichloromethane at 20℃; for 4h; Sealed tube;	84%

1,4-bis(dimethylsilyl)benzene (2488-01-9) + dimethoxy(diphenyl)silane (6843-66-9) → polymer, Mw 30292 Da, Mw/Mn 2.78; monomer(s): 1,4-bis(dimethylsilyl)benzene; diphenyldimethoxysilane

Conditions	Yield
With tris(pentafluorophenyl)borate In toluene for 3h;	83%

1,4-bis(dimethylsilyl)benzene (2488-01-9) + dimethoxy(methyl)phenylsilane (3027-21-2) → polymer, Mw 11.7 KDa, Mw/Mn 1.65; monomer(s): 1,4-bis(dimethylsilyl)benzene; methylphenyldimethoxysilane

Conditions	Yield
With tris(pentafluorophenyl)borate In toluene	80%

1,4-bis(dimethylsilyl)benzene (2488-01-9) + C10H11BrS → 1,4-bis((3-((4-bromophenyl)thio)-2-methylpropyl)dimethylsilyl)benzene

Conditions	Yield
With bis(1,5-cyclooctadiene)diiridium(I) dichloride In 1,4-dioxane at 20℃; Inert atmosphere;	80%

Upstream product

• 1066-35-9 dimethylmonochlorosilane 
• 106-46-7 para-dichlorobenzene 
• 106-37-6 1.4-dibromobenzene 

Downstream Products

• 84584-56-5 C₂₄H₄₄N₂O₂Si₂ 
• 1251461-43-4 C₃₄H₅₄Si₆ 
• 1251461-45-6 C₇₄H₇₀Si₆ 
• 18753-27-0 1,4-bis(dimethyl(phenyl)silyl)benzene 

Relevant articles and documents

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