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Chemical Structure| 2488-01-9 Chemical Structure| 2488-01-9

Structure of 1,4-Bis(dimethylsilyl)benzene
CAS No.: 2488-01-9

Chemical Structure| 2488-01-9

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Product Details of [ 2488-01-9 ]

CAS No. :2488-01-9
Formula : C10H18Si2
M.W : 194.42
SMILES Code : C[SiH](C1=CC=C([SiH](C)C)C=C1)C
MDL No. :MFCD00039790
InChI Key :UHXCHUWSQRLZJS-UHFFFAOYSA-N
Pubchem ID :6328729

Safety of [ 2488-01-9 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 2488-01-9 ] Show Less

Physicochemical Properties

Num. heavy atoms 12
Num. arom. heavy atoms 6
Fraction Csp3 0.4
Num. rotatable bonds 2
Num. H-bond acceptors 0.0
Num. H-bond donors 0.0
Molar Refractivity 63.46
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

0.0 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

3.11
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

4.23
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

1.07
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

3.56
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

0.67
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.53

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-3.95
Solubility 0.0219 mg/ml ; 0.000113 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-3.94
Solubility 0.0223 mg/ml ; 0.000115 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-4.16
Solubility 0.0135 mg/ml ; 0.0000697 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Moderately soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

Low
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

No
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

Yes
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

Yes
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-4.48 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

2.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

1.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<2.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

3.45

Application In Synthesis of [ 2488-01-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 2488-01-9 ]

[ 2488-01-9 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 2488-01-9 ]
  • [ 5666-17-1 ]
  • [ 142414-26-4 ]
  • [ 142414-33-3 ]
  • 2
  • [ 2488-01-9 ]
  • [ 2754-32-7 ]
YieldReaction ConditionsOperation in experiment
92% A double-necked round-bottom flask was set up with a reaction device on which a reflux tube was placed, and the inside was dried and removed, and replaced with a nitrogen atmosphere. Measure the pre-dried anhydrous methanol (250 ml) into a reaction device and place the reaction device in an ice water bath. Under a nitrogen or argon atmosphere, 6.3 g (274.2 mmol) of sodium metal cut into small pieces was carefully added successively. After the metal sodium had completely reacted with methanol and no hydrogen bubbles were generated, a first solution of sodium methoxide was prepared. Weighing 17.8 g (91.4 millimoles) of dioxane of structural formula (A-1) in a feeding tube, Pre-dried anhydrous methanol (50 ml) was added to the feed tube to prepare a bis-decane solution of structural formula (A-1), which was the second solution. The rate of dropwise addition was controlled and the second solution was slowly fed into the first solution in the reaction apparatus. Hydrogen bubbles continued to be generated during the addition. After the dropwise addition was completed, stirring was continued at room temperature for 10 minutes until the generation of hydrogen gas was moderated until it subsided, which was the third solution. Then, a mixed solution of 11.0 g (274.2 millimoles) and water (150 ml) of pre-formulated sodium hydroxide was slowly added dropwise to the third solution, and stirring was continued at room temperature for 20 minutes. This is the fourth solution, and the hydrolysis reaction has been completed so far. After the reaction was completed, a saturated aqueous solution of ammonium chloride was gradually added to the fourth solution for neutralization, and the mixture was cooled in an ice-water bath and stirred for 20 minutes. This was the fifth solution. The fifth solution was transferred to a separatory funnel and extracted with ether (200 ml/3 times). The organic layer was collected and washed with saturated brine (300 ml), dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to give the crude product of the white solid as the phenylephrine of formula (I-1). N-hexane was added to the crude white solid product of the phenylenedioxylanol of formula (I-1). After thorough and uniform mixing, the mixture was collected by suction filtration. The white filter cake was washed with n-hexane, and the white solid product was collected and dried to obtain 19.1 g of the bis-stanol product of formula (I-1). The yield was 92%.
92% Synthesis of compound (I-1): Setup a reaction device, such as a reflux pipe, on a two-necked round bottom flask. Dry the inside of the two-necked round bottom flask. Introduce nitrogen gas into the two-necked round bottom flask. Put 250 mL of pre-dried anhydrous methanol in the reaction device. Place the reaction device in an ice water bath. Chips of 6.3 g (274.2 mmol) of metallic sodium are put in the reaction device immersed in the ice water bath under nitrogen gas or argon gas atmosphere one by one and carefully. After the metallic sodium has reacted with methanol completely and no hydrogen bubbles have been generated, the first solution of sodium methoxide is produced. Then, 17.8 g (91.4 mmol) of disilane with structural formula (A-1) and 50 mL of pre-dried anhydrous methanol are introduced into the feeding pipe to form a disilane (expressed by structural formula (A-1)) solution known as the second solution. Drip the second solution slowly to the first solution in the reaction device while hydrogen bubbles are being continuously generated. Afterward, the mixture of first and second solutions are stirred for 10 minutes at room temperature while the generation of hydrogen gas is fading out, thereby producing the third solution. Then, an aqueous solution of a mixture of 11.0 g (274.2 mmol) of sodium hydroxide and 150 mL of water is dripped slowly to the third solution while the third solution is being stirred for 20 minutes, so as to produce the fourth solution. At this point in time, the hydrolysis process is finished, and a saturated ammonium chloride aqueous solution is added to the fourth solution to trigger neutralization therebetween while the fourth solution is being cooled and stirred in an ice water bath for 20 minutes to produce the fifth solution. Transfer the fifth solution to a separatory funnel to undergo extraction with 200 mL of ether thrice, and then collect the organic supernatant before rinsing it with 300 mL of saturated brine solution for the sake of drying. A drying process is performed with anhydrous magnesium sulfate, and then filtration is performed so that the filtrate is depressurized and concentrated to obtain a crude white solid product of phenylene disilanol with structural formula (I-1). Add n-hexane to the crude white solid product of phenylene disilanol with structural formula (I-1) and mix them. Collect the solid precipitate by suction filtration. Rinse the white solid with n-hexane. Collect the white solid product and dry it to obtain 19.1 g of disilanol with structural formula (I-1) at a yield of 92%. Referring to FIG. 4, it shows the 1H-NMR spectrum for phenylene disilanol according to an embodiment of the present invention.
  • 5
  • [ 1066-35-9 ]
  • [ 106-37-6 ]
  • [ 2488-01-9 ]
YieldReaction ConditionsOperation in experiment
98% With magnesium; In tetrahydrofuran; at 50 - 85℃; for 16h;Inert atmosphere; A three-neck round bottom flask is set up with a reaction device on which a feeding pipe and a return pipe are installed. 6.1 g (0.25 moles) of magnesium metal was weighed and placed in a three-necked flask reaction apparatus, and the inside thereof was dried to remove water and replaced with a nitrogen or argon atmosphere. The tetrahydrofuran (20 ml) was slowly added to the reaction apparatus and covered with magnesium metal sufficiently. After the reaction mixture was kept in a stable state, 27.9 ml (0.25 millimolar) of dimethylchlorosilane (Me2HSiCl) was slowly added dropwise to the reaction apparatus. This was the first solution. Separately, dibromobenzene, 24.7 g (0.11 mole) and tetrahydrofuran (60 ml), were placed in a feeding tube or a dose pump to be mixed into a dibromobenzene solution, which was the second solution. A small amount (approximately 0.5 ml) of the second solution is slowly added dropwise to the first solution in the reaction device to initiate the Grinnard reaction. The dripping rate was controlled and the feed was slowly fed into the reaction apparatus so that the reaction mixture was maintained in a non-boiling state at a reaction temperature of about 50 to 60C. After the addition was completed, dibromobenzene in the feed tube was rinsed with a small amount of tetrahydrofuran (5 to 10 ml) into the reactor as a third solution, which was heated to reflux for 16 hours. If there is a device temperature sensor, the internal reaction temperature required for the reflux of tetrahydrofuran is 65 C. If the temperature sensor is not installed, the temperature of the oil bath is about 75 C ~ 85 C, depending on the size of the reaction device. After the reaction was completed, distilled water (150 ml) was slowly added dropwise to the third solution in the reaction apparatus to quench the reaction. After continuous stirring for 5 to 10 minutes, two immiscible solutions were obtained, which was the fourth solution. The fourth solution was transferred to a separatory funnel, and the aqueous layer was extracted with ether (60 ml/time, 3 times) to collect the upper organic solvent layer. Separately wash with water (100 ml) and dry saturated brine (120 ml). After drying over anhydrous sodium sulfate followed by filtration, the filtrate was concentrated under reduced pressure to give 20.4 g of the dinonane product of formula (A-1) in 98% yield.
98% Setup a reaction device, such as a feeding pipe and a reflux pipe, on a three-necked round bottom flask. Put 6.1 g (0.25 mol) of metallic magnesium in the three-necked round bottom flask. Dry the inside of the three-necked round bottom flask. Introduce nitrogen gas or argon gas into the three-necked round bottom flask. Introduce 20 mL of tetrahydrofuran into the reaction device slowly, cover it fully with metallic magnesium, and stir the reactants. Introduce 27.9 mL (0.25 mmol) of dimethylsilyl chloride (Me2HSiCl) into the reaction device slowly, thereby producing the first solution. Producing the second solution entails introducing 24.7 g (0.11 mol) of dibromobenzene and 60 mL of tetrahydrofuran into the feeding pipe or a dosage transmission pump to blend the dibromobenzene solution. Drip 0.5 mL of the second solution slowly to the first solution in the reaction device, so as to trigger the Grignard reaction. Then, feed the mixed first and second solutions to the reaction device slowly enough to prevent the reacting mixture from boiling; meanwhile, the reaction temperature ranges from 50 C. to 60 C. Afterward, residual dibromobenzene in the feeding pipe is washed into the reaction device by 510 mL of tetrahydrofuran to produce the third solution, and then the third solution is heated and refluxed for 16 hours. In the presence of a device temperature sensor, the reflux of tetrahydrofuran requires an internal reaction temperature of 65 C. In the absence of any device temperature sensor, the reflux of tetrahydrofuran requires an oil or sand bath tank temperature of 75 C.85 C., depending on the size of the reaction device. Upon completion of the reaction, 150 mL of distilled water is slowly introduced into the third solution in the reaction device to trigger a quenching reaction, and then the third solution is stirred continuously for 510 minutes to form two layers of immiscible solution known as the fourth solution. Transfer the fourth solution to a separatory funnel to extract the aqueous layer with 60 mL of ether thrice, and then collect the organic supernatant before rinsing it with 100 mL of water and 120 mL of saturated saline solution for the sake of drying. A drying process is performed with anhydrous sodium sulfate, and then filtration is performed so that the filtrate is depressurized and concentrated to obtain 20.4 g of disilane structural formula (A-1), with a yield of 98%. Referring to FIG. 3, it shows the 1H-NMR spectrum for phenylene disilane according to an embodiment of the present invention.
84.7 - 90.5% With magnesium; In diethyl ether; toluene; [0028] A series of runs was made using a co-solvent comprising diethyl ether and toluene, using procedures similar to those utilized in Example 3, to prepare 1,4-bis(dimethylsilyl)benzene from the reaction of either 1,4-dibromobenzene or 1,4-dichlorobenzene and Me2HSiCl.
In tetrahydrofuran; water; Synthetic Example 1 A 2-liter flask equipped with a stirrer, reflux condenser, thermometer and dropping funnel was charged with 48.6 g (2.0 mol) of metallic magnesium, 600 ml of tetrahydrofuran, and a small amount of iodine. To the flask kept at 50 to 60 C. in a nitrogen gas atmosphere, 235.9 g (1.0 mol) of p-dibromobenzene in 400 ml of tetrahydrofuran was added over 3 hours from the dropping funnel. The contents were stirred for 5 hours under reflux. To the resulting Grignard reagent under water cooling, 189.2 g (2.0 mol) of dimethylchlorosilane was added dropwise over 2 hours from the dropping funnel. The contents were stirred for 3 hours under reflux. To this reaction solution was added 400 g of water. By liquid separating operation, the upper or organic layer was separated, from which a fraction of 73 to 75 C. at 6 mmHg was collected by distillation, yielding 140.0 g of 1,4-bis(dimethylsilyl)benzene.

  • 6
  • [ 2488-01-9 ]
  • polymer, poly[1,4-bis(hydroxydimethylsilyl)benzene], Mn = 2840, polydispersity = 1.03 [ No CAS ]
  • 7
  • C25H25NO*F6P(1-)*H(1+) [ No CAS ]
  • [ 2488-01-9 ]
  • [ 14174-09-5 ]
  • C60H68N2O2Si2*2C24H32O8*2F6P(1-)*2H(1+) [ No CAS ]
  • 8
  • C38H68O12Si8 [ No CAS ]
  • [ 2488-01-9 ]
  • C48H86O12Si10 [ No CAS ]
  • 9
  • [ 2488-01-9 ]
  • [ 1112-39-6 ]
  • polymer, Mw 49.1 KDa, Mw/Mn 2.24; monomer(s): 1,4-bis(dimethylsilyl)benzene; dimethyldimethoxysilane [ No CAS ]
  • 10
  • [ 2488-01-9 ]
  • [ 3027-21-2 ]
  • polymer, Mw 11.7 KDa, Mw/Mn 1.65; monomer(s): 1,4-bis(dimethylsilyl)benzene; methylphenyldimethoxysilane [ No CAS ]
  • 11
  • [ 2488-01-9 ]
  • [ 6843-66-9 ]
  • polymer, Mw 30292 Da, Mw/Mn 2.78; monomer(s): 1,4-bis(dimethylsilyl)benzene; diphenyldimethoxysilane [ No CAS ]
  • 12
  • [ 2488-01-9 ]
  • [ 169391-48-4 ]
  • polymer, Mw 22.2 kDa, PDI 1.73; monomer(s): 1,4-bis[4-(4-pentenyloxy)benzoyl]hydroquinone; 1,4-bis(dimethylsilyl)benzene [ No CAS ]
  • 13
  • [ 2488-01-9 ]
  • [ 521062-81-7 ]
  • polymer, Mw 60.9 kDa, PDI 1.59; monomer(s): 2-tert-butyl-1,4-bis[4-(4-pentenyloxy)benzoyl]hydroquinone; 1,4-bis(dimethylsilyl)benzene [ No CAS ]
  • 14
  • [ 2488-01-9 ]
  • ({4-[Dimethyl-(2-oxo-vinyl)-silanyl]-phenyl}-dimethyl-silanyl)-ethenone [ No CAS ]
  • 15
  • [ 2488-01-9 ]
  • [4-(Ethoxyethynyl-dimethyl-silanyl)-phenyl]-dimethyl-silanyl}-ethenone [ No CAS ]
  • 16
  • [ 2488-01-9 ]
  • [ 181211-84-7 ]
  • 17
  • [ 2488-01-9 ]
  • [ 144601-30-9 ]
  • 18
  • [ 2488-01-9 ]
  • 1,4-Bis-[dimethyl-(2,3,4,5-tetramethyl-cyclopenta-2,4-dienyl)-silanyl]-benzene [ No CAS ]
  • 19
  • [ 2488-01-9 ]
  • 1,4-Bis-[(2,4-di-tert-butyl-cyclopenta-2,4-dienyl)-dimethyl-silanyl]-benzene [ No CAS ]
  • 20
  • [ 1066-35-9 ]
  • [ 106-46-7 ]
  • [ 2488-01-9 ]
YieldReaction ConditionsOperation in experiment
95% With Tris(3,6-dioxaheptyl)amine; sodium; In 5,5-dimethyl-1,3-cyclohexadiene; at 100 - 110℃; for 7h; In a 1000 mL reaction flask,Put in xylene 230g,Sodium metal 47g,TDA-1 0.37g,Warm up to 100110C,Insulation 0.5h,Turn on stirringAfter stirring for 1 hour, all the sodium was made into sodium sand,Sodium sand mixture is formed.After 73.5 g of p-dichlorobenzene and 100 g of xylene were mixed and dissolved,Then add 96.5g dimethylchlorosilane,Form a mixture,The mixture was added to a constant pressure funnel.The liquid droplets in the constant pressure funnel are added to the sodium sand mixture. Dropping about 5h to complete,Then the reaction was completed by keeping at 100-110C for 2 hours.After the reaction,Cool the reaction system to 5-15C.Then add 280 mL of water from the constant pressure funnel.Stirring 1h,Stand for 1h,Then separate the lower brine phase,The upper organic phase is taken as the crude 1,4-bis (dimethylsilyl) benzene.The upper organic phase into the distillation flask,The temperature in the control bottle is below 120C.Vacuum vacuum distillation,92 g of 1,4-bis (dimethylsilyl) benzene was obtained,The yield is 95%.Purity greater than 99%.
86.6 - 89.5% With magnesium; In diethyl ether; toluene; [0028] A series of runs was made using a co-solvent comprising diethyl ether and toluene, using procedures similar to those utilized in Example 3, to prepare 1,4-bis(dimethylsilyl)benzene from the reaction of either 1,4-dibromobenzene or 1,4-dichlorobenzene and Me2HSiCl.
  • 21
  • [ 2488-01-9 ]
  • [ 7688-51-9 ]
  • [ 20152-18-5 ]
YieldReaction ConditionsOperation in experiment
92% In methanol; 5,5-dimethyl-1,3-cyclohexadiene; Example 1 A 1-liter glass flask equipped with a stirrer, reflux condenser, thermometer and dropping funnel was charged with 201.5 g (1.0 mol) of N,N-bis(trimethylsilyl)-allylamine and 0.33 g of a 3% xylene solution of platinum 1,3-divinyltetramethyldisiloxane complex. To the flask kept at 60 to 65 C., 97.2 g (0.5 mol) of 1,4-bis-(dimethylsilyl)benzene was added dropwise over 3 hours from the dropping funnel. The reaction solution was allowed to ripen for 2 hours. 192.0 g (6.0 mol) of methanol was added to the reaction solution, which was kept under reflux for reaction for 6 hours. From the reaction solution, a fraction of 163 to 165 C. at 1 mmHg was collected in a yield of 142.0 g by vacuum distillation. By mass spectroscopy (MS), nuclear magnetic resonance spectroscopy (NMR), and infrared absorption spectroscopy (IR), the compound thus obtained was identified to be 1,4-bis(3-aminopropyldimethylsilyl)benzene (yield 92%). Also, by gas chromatography, the compound was found to be free of isomers. MS: m/z (attribution) 308 (molecular ion (M+) peak) 293 (M+-CH3 ion peak) 116 (Si(CH3)2(CH2CH2CH2NH2) ion peak)
  • 22
  • [ 2488-01-9 ]
  • [ 96-05-9 ]
  • 1,4-bis-(dimethyl-[3-(methacryloyloxy)propyl]silyl)benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
platinum 1,3-divinyl-1,1,3,3-tetramethyldisiloxane; In toluene; xylene; at 20℃; for 17h; A mixture of 1,4-bis-dimethylsilylbenzene (Gelest, Tulleytown, PA) (5.0Og, 25.7 millmole (mmol)), allyl methacrylate (Sigma-Aldrich) (6.49 g, 51.4 mmol), toluene (20 milliliter (ml)), and two drops of a solution of platinum - divinyltetramethyldisiloxane complex in xylene (Gelest) was mixed at room temperature for 17 hours. The resulting mixture was loaded onto a silica gel column and eluted with a mixture of ethyl acetate (20 volume percent (vol%)) in hexane (80 vol%). The solvent was evaporated to yield the product as a colorless oil (7.80 g) having a MW of 446.74 and a viscosity of 136 cP. Characterization of the oil by IH Nuclear Magnetic Resonance Spectroscopy (NMR) and Infrared Spectroscopy (IR) spectra was consistent with the p-PDA structure.
  • 23
  • [ 2488-01-9 ]
  • [ 16839-48-8 ]
  • 1,4-bis-(dimethyl-[3-(2-methacryloyloxyethyloxy)propyl]silyl)benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
platinum 1,3-divinyl-1,1,3,3-tetramethyldisiloxane; In toluene; xylene; at 20℃; for 24h; mixture of 1,4-bis-dimethylsilyl benzene (2.86, 15 mmol), 2-allyloxyethyl methacrylate (Monomer-Polymer & Dajac Labs, Inc., Feasterville, PA) (5.00 g, 30 mmol), toluene (15 ml), and two drops of a solution of platinum - divinyltetramethyldisiloxane complex in xylene was mixed at room temperature for 24 hours. The mixture was loaded onto a silica gel column and eluted with a mixture of ethyl acetate (20 vol%) in hexane (80 vol%). The solvent was evaporated to yield the product as a colorless oil (6.45 g) having a MW of 534.85 and a viscosity of 32 cP. Characterization of the oil by IH NMR and IR spectra was consistent with the p-PDE structure.
  • 24
  • [ 2488-01-9 ]
  • [ 13007-92-6 ]
  • [ 75830-40-9 ]
  • 25
  • [ 2488-01-9 ]
  • [ 61117-58-6 ]
  • [ 75830-42-1 ]
  • 26
  • [ 2488-01-9 ]
  • [Pt3H(PEt3)3(μ-PPh2)3] [ No CAS ]
  • [Pt3(SiMe2C6H4SiMe2H)(PEt3)2(μ-PPh2)3] [ No CAS ]
  • 27
  • [ 2488-01-9 ]
  • [ 7539-12-0 ]
  • C4H4O3*C24H34O6Si2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% Into a 500 ml flask fitted with a stirrer, a thermometer, and a condenser were charged 101.6 g (0.726 mol) of allylsuccinic anhydride, 1 g of a 2% ethanol solution of chloroplatinic acid, and 150 g of toluene, followed by heating on an oil bath under stirring so that the inner temperature became 70 C. Then, 58.2 g (0.33 mol) of <strong>[2488-01-9]1,4-bis(dimethylsilyl)benzene</strong> was added dropwise over a period of 20 minutes. After the dropwise addition was completed, the whole was stirred at 90 C. for 3 hours. When the resulting reaction product was analyzed by gas chromatography, the peak derived from <strong>[2488-01-9]1,4-bis(dimethylsilyl)benzene</strong> as a starting material had disappeared. The reaction liquid was concentrated under reduced pressure under conditions of 120 C./10 hPa for 5 hours to obtain 143 g (95% yield) of a white solid. As a result of analysis of the white solid by 1H-NMR, it was found that the solid was a compound represented by the following structure.
  • 28
  • [ 2488-01-9 ]
  • [ 1109-15-5 ]
  • [ 3376-52-1 ]
  • C6H4(Si(CH3)2PH(C6H5)B(C6F5)3)2 [ No CAS ]
  • 29
  • [ 2488-01-9 ]
  • [ 1159842-18-8 ]
  • [ 1251461-43-4 ]
YieldReaction ConditionsOperation in experiment
platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex; In hexane; for 0.0333333h; Example 8Synthesis of the crosslinker 4a from 3a and <strong>[2488-01-9]1,4-bis(dimethylsilyl)benzene</strong>-1,4-Bis(dimethylsilyl)benzene (0.1 g, 0.514 mmol) and 3a (0.225 g, 1.028 mmol) were mixed in 2 mL of hexane in a vial and 90 μL (9.90 μmol of Pt) of the Karstedt catalyst solution was added and the mixture was mixed vigorously for 2 min using a mechanical stirrer to obtain a viscous product. FT-IR: ν (-C≡C-C≡C-): 2072 cm-1 and ν (-CHCH2): 1596 cm-1. 1H NMR (in ppm): 7.67 (C6H5-), 6.22-5.86 (-CHCH2) and (0.473 (of <strong>[2488-01-9]1,4-bis(dimethylsilyl)benzene</strong>), 1.84 (-Si-CH2-CH2-Si-, sp2 C), 0.278 (of 3a)) (-CH3). 13C NMR (in ppm): (138.76, 133.66) (-CHCH-, phenyl) (136.26, 134.92) (-CHCH2, alkene) (sp2 C), (89.98, 85.04) (-C≡C-C≡C-) (sp C), 1.52 (-Si-CH2-CH2-Si-, sp C), and (-1.02, -3.12) (-CH3) (sp3 C).
  • 30
  • [ 2488-01-9 ]
  • [ 1159842-19-9 ]
  • [ 1251461-45-6 ]
YieldReaction ConditionsOperation in experiment
platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex; In hexane; for 0.0333333h; Example 11Synthesis of the crosslinker 4b from 3b and <strong>[2488-01-9]1,4-bis(dimethylsilyl)benzene</strong>-1,4-Bis(dimethylsilyl)benzene (0.1 g, 0.514 mmol) and 3b (0.480 g, 1.028 mmol) were mixed in 2 mL of hexane in a vial and 90 μL (9.90 μmol of Pt) of the Karstedt catalyst solution was added and the mixture was mixed vigorously for 2 min using a mechanical stirrer to obtain a viscous product. FT-IR: ν (-C≡C-C≡C-): 2072 cm-1 and ν (-CHCH2): 1596 cm-1. 1H NMR (in ppm): 7.68-7.38 (C6H5-) (of 3b)), 7.72 (C6H5-) (of <strong>[2488-01-9]1,4-bis(dimethylsilyl)benzene</strong>), 6.58-6.05 (-CHCH2) 1.92 (-Si-CH2-CH2-Si-, sp2 C), and (0.473) (-CH3). 13C NMR (in ppm): (138.23, 135.82, 130.58, 128.25) (C6H5- of 3b) (sp2 C) (138.82, 133.74) (-CHCH-, phenyl of <strong>[2488-01-9]1,4-bis(dimethylsilyl)benzene</strong>) (136.26, 134.92) (-CHCH2, alkene) (sp2 C), (89.98, 85.04) (-C≡C-C≡C-) (sp C), 1.62 (-Si-CH2-CH2-Si-, sp2 C), and (-3.12) (-CH3) (sp3 C). DSC analysis (from RT to 400 C. at 10 C./min) in N2 of 4b: Melting endotherm at 105 C. and exotherm at 315 C.
  • 32
  • [ 2488-01-9 ]
  • [ 536-74-3 ]
  • [ 1422469-27-9 ]
  • 33
  • [ 2488-01-9 ]
  • [ 598-25-4 ]
  • 1,4-bis(dimethyl(3-methylbut-1-en-2-yl)silyl)benzene [ No CAS ]
  • 34
  • [ 2488-01-9 ]
  • [ 5664-17-5 ]
  • 1,4-bis((3-cyclohexylprop-1-en-2-yl)dimethylsilyl)benzene [ No CAS ]
 

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