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[ CAS No. 1185-55-3 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
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Chemical Structure| 1185-55-3
Chemical Structure| 1185-55-3
Structure of 1185-55-3 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 1185-55-3 ]

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Product Details of [ 1185-55-3 ]

CAS No. :1185-55-3 MDL No. :MFCD00008342
Formula : C4H12O3Si Boiling Point : No data available
Linear Structure Formula :Si(OCH3)3(CH3) InChI Key :BFXIKLCIZHOAAZ-UHFFFAOYSA-N
M.W : 136.22 Pubchem ID :14456
Synonyms :
Chemical Name :Trimethoxy(methyl)silane

Calculated chemistry of [ 1185-55-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 32.47
TPSA : 27.69 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.66 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.26
Log Po/w (XLOGP3) : 0.67
Log Po/w (WLOGP) : 0.49
Log Po/w (MLOGP) : -1.06
Log Po/w (SILICOS-IT) : -1.34
Consensus Log Po/w : 0.2

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.91
Solubility : 16.8 mg/ml ; 0.123 mol/l
Class : Very soluble
Log S (Ali) : -0.83
Solubility : 20.2 mg/ml ; 0.149 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.72
Solubility : 25.7 mg/ml ; 0.189 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 4.1

Safety of [ 1185-55-3 ]

Signal Word:Danger Class:3
Precautionary Statements:P260-P240-P210-P233-P243-P241-P242-P271-P264-P280-P370+P378-P314-P337+P313-P305+P351+P338-P303+P361+P353-P332+P313-P304+P340+P312-P403+P233-P403+P235-P405-P501 UN#:1993
Hazard Statements:H316-H320-H373-H336-H225 Packing Group:Ⅱ
GHS Pictogram:

Application In Synthesis of [ 1185-55-3 ]

* 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 [ 1185-55-3 ]

[ 1185-55-3 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 1185-55-3 ]
  • phenylmagnesium bromide [ No CAS ]
  • [ 3027-21-2 ]
  • 2
  • [ 3277-26-7 ]
  • [ 1185-55-3 ]
  • [ 60111-52-6 ]
YieldReaction ConditionsOperation in experiment
62.8% Comparative Example 2 A 1000-ml four necked glass flask equipped with a reflux condenser, thermometer and stirrer was purged with nitrogen. The flask was charged with 136.2 g (1.0 mol) of methyltrimethoxysilane, 372.8 g (2.0 mol) of 1,1,3,3-tetramethyl-1,3-divinyldisiloxane and 96.0 g (2.0 mol) of methanol, and cooled in an ice water bath to an internal temperature below 10C. To the flask kept at an internal temperature of 5-10C, 9.8 g (0.1 mol) of conc. sulfuric acid was added dropwise over 15 minutes, and stirring was continued at the temperature for 30 minutes. Subsequently, at a temperature of 5-25C, 105.0 g (5.83 mol) of water was added dropwise over one hour. After the completion of dropwise addition, stirring was continued at 15-25C for 2.5 hours. The aqueous layer was removed from the reaction solution, after which the organic layer was washed with aqueous sodium bicarbonate and then with water. On distillation of the resulting organic layer, 217.0 g (0.63 mol) of methyltris(trimethylsiloxy)silane with a purity of 99.7% was collected as a fraction having a boiling point of 102.0-103.0C/1.3 kPa. The yield was 62.8%.
  • 3
  • [ 1185-55-3 ]
  • [ 2627-95-4 ]
  • MeSi(OH)(OSiMe2Vi)2 [ No CAS ]
  • MeSi(OMe)(OSiMe2Vi)2 [ No CAS ]
  • [ 60111-52-6 ]
YieldReaction ConditionsOperation in experiment
79.4% Example 7 A 1000-ml four necked glass flask equipped with a reflux condenser, thermometer and stirrer was purged with nitrogen. The flask was charged with 372.8 g (2.0 mol) of 1,3-divinyl-1,1,3,3-tetramethyldisiloxane and 64.0 g (2.0 mol) of methanol, and cooled in an ice water bath to an internal temperature below 10C. To the flask kept at an internal temperature of 5-10C, 9.8 g (0.1 mol) of conc. sulfuric acid was added dropwise over 30 minutes, and stirring was continued at the temperature for 30 minutes. Subsequently, to the flask kept at an internal temperature of 5-10C, 136.2 g (1.0 mol) of methyltrimethoxysilane was added dropwise over 30 minutes, and stirring was continued at the temperature for one hour. At an internal temperature of 5-25C, 105.0 g (5.8 mol) of water was added dropwise over one hour. After the completion of dropwise addition, stirring was continued at 15-25C for 2.5 hours. The organic layer of the reaction solution was analyzed by GC, finding that the area percent ratio of the main product to monomethoxy and monohydroxy compounds, MeSi (OSiMe2Vi)3/ [MeSi(OMe) (OSiMe2Vi)2 + MeSi(OH)(OSiMe2Vi)2] was 13.2. The total content of monomethoxy and monohydroxy compounds was 0.074 mol, as determined from the area percents by GC. The reaction solution was subjected to separatory operation to remove the aqueous layer. While the organic layer was kept at a temperature of 20-25C, 34.3 g (0.35 mol) of conc. sulfuric acid was added dropwise over 15 minutes, and stirring was continued at the temperature for 0.5 hour. The organic layer after reaction with sulfuric acid was analyzed by GC, finding that the area percent ratio of the main product to monomethoxy and monohydroxy compounds, MeSi (OSiMe2Vi)3/[MeSi(OMe) (OSiMe2Vi)2 + MeSi(OH)(OSiMe2Vi) 2] was 2990.7. The sulfuric acid layer was removed from the reaction solution, after which the organic layer was washed with water, neutralized with aqueous sodium bicarbonate, and washed with water again. On distillation of the resulting organic layer, 275.3 g (0.79 mol) of methyltris(dimethylvinylsiloxy)silane with a purity of 99.7% was collected as a fraction having a boiling point of 95.0-96.5C/0.9 kPa. The yield was 79.4%.
  • 4
  • [ 1185-55-3 ]
  • [ 947-42-2 ]
  • [ 476161-46-3 ]
  • [ 6843-66-9 ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran; at 23℃; for 24h; Diphenylsilanediol (60 g), tetrahydrofuran (THF, 30 g) and methyltrimethoxysilane (MTMOS, 180 g) were placed in a 500 mL 3-neck round bottom flask with a stir bar and reflux condenser. The reaction was allowed to proceed without ammonia catalyst for 24 hours at +23C. GC/MS showed that no desired reaction had taken place. Only some alkoxy/OH exchange between silanediol and MTMOS had occurred, to give methoxydiphenylsilanol and dimethoxydiphenylsilane.
  • 5
  • [ 1185-55-3 ]
  • [ 947-42-2 ]
  • [ 10175-48-1 ]
  • [ 6843-66-9 ]
YieldReaction ConditionsOperation in experiment
With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at -20℃; for 5h; Diphenylsilanediol (60 g), tetrahydrofuran (THF, 30 g) and methyltrimethoxysilane (MTMOS, 180 g) were placed in a 500 mL 3-neck round bottom flask with a stir bar and reflux condenser. The flask was cooled to -20C. l,8-Diazabicycloundec-7-ene (DBU, 0.5 g) was added into the solution. The reaction was allowed to proceed for 5 hours at -20C, after which GC/MS was run from the reaction mixture. It showed, that while low yields of the desired product was formed, over 80% of diphenylsilanediol was converted to dimethoxydiphenylsilane. DBU (pKb = 1.1) was clearly too strong base for this reaction and caused excessive side reactions
  • 6
  • [ 75-79-6 ]
  • [ 1185-55-3 ]
  • [ 108-90-7 ]
  • [ 3027-21-2 ]
YieldReaction ConditionsOperation in experiment
99.6% Into a four-necked flask, 12 g of magnesium powder (0.5mol), 18 g of tetrahydrofuran (0.25mol), methyltrimethoxysilane 9.5G (0.07mol), chlorobenzene 3.4 g (0.03mol); was stirred and heated to reflux to start the reaction. Under reflux for about 1 hourSolution containing 90.1 g (0.8mol) of chlorobenzene, 29.9 g (0.2mol) methyl trichlorosilane and 177 g (1.3mol) methyltrimethoxysilane A mixed solution of methoxysilane; refluxing continued for 6.5h; cooled to room temperature, suction filtered, washed with an appropriate amount of methyltrimethoxysilane cakeTwice the combined filtrate is the crude product. By gas chromatographic analysis, the yield of methyl phenyl dimethoxysilane was 85.5percent (magnesiumCalculation). The crude product was distilled at atmospheric pressure to recover unreacted material, a vacuum distillation to give the product methylphenyl dimethoxysilane, purity99.6percent.
  • 7
  • [ 1185-55-3 ]
  • [ 108-90-7 ]
  • [ 3027-21-2 ]
YieldReaction ConditionsOperation in experiment
87% With 15-crown-5; sodium; at 38℃; for 2h; Sodium metal particles suspension was added to a mixture of 62.5 g of chlorobenzene and 227 g of methyltrimethoxysilane, and then 0.32 g of 15-crown-5 was added. The reaction was carried out at 38 ° C for 2 h , The reaction was stopped, and the reaction mixture was filtered and vacuum-distilled to give methylphenyldimethoxysilane in a yield of 87percent.
  • 8
  • [ 108-86-1 ]
  • [ 1185-55-3 ]
  • [ 3027-21-2 ]
YieldReaction ConditionsOperation in experiment
80% With sodium; at 38℃; for 2h; A suspension of sodium metal particles was added to a mixture of 87. 22 g of bromobenzene and 227 g of methyltrimethoxysilane,Then added0.32 g of cyclodextrin,The reaction was stopped at 38 ° C for 2 h, and the reaction mixture was filtered and reduced in vacuum to give methylphenyldimethoxysilane in a yield of 80percent.
  • 9
  • [ 1185-55-3 ]
  • [ 100-59-4 ]
  • [ 3027-21-2 ]
  • [ 18407-48-2 ]
YieldReaction ConditionsOperation in experiment
31%; 17% In tetrahydrofuran; for 1h; (This example, as a comparative example, does not include the addition of 241 g of methyltrimethoxysilane and 1000 mL of tetrahydrofuran in a 5 L four-necked bottle within the scope of the present invention, starting with stirring, dropping 1030 mL of 1.72 mol / L Chlorophenyl Grignard reagent in tetrahydrofuran After 1 hour of reaction, most of the tetrahydrofuran was distilled off and 1000 mL of xylene was added and the remaining tetrahydrofuran was distilled off and allowed to cool to room temperature and filtered to give 99 g of phenylmethyldi Methoxysilane (yield 31percent) and 69 g of diphenylmethylmethoxysilane (yield 17percent).
  • 10
  • [ 1185-55-3 ]
  • [ 100-58-3 ]
  • [ 3027-21-2 ]
YieldReaction ConditionsOperation in experiment
95% In diethyl ether; for 1h;Reflux; 5L four-necked flask by adding 240g methyltrimethoxysilane and 1000mL ether, stirring drop 1080mL 1.63mol / L bromobenzene reagent ether solution; drop Bi, heated reflux 1h .; cooling, to the reaction (Yield 95percent) of phenylmethyldimethoxysilane and 4 g of diphenylmethoxysilane (yield 1percent) were added to the filtrate by adding 1000 mL of n-hexane and then filtering.
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