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Chemical Structure| 1185-55-3 Chemical Structure| 1185-55-3

Structure of Trimethoxymethylsilane
CAS No.: 1185-55-3

Chemical Structure| 1185-55-3

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Product Details of [ 1185-55-3 ]

CAS No. :1185-55-3
Formula : C4H12O3Si
M.W : 136.22
SMILES Code : C[Si](OC)(OC)OC
MDL No. :MFCD00008342
InChI Key :BFXIKLCIZHOAAZ-UHFFFAOYSA-N
Pubchem ID :14456

Safety of [ 1185-55-3 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H316-H320-H373-H336-H225
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
Class:3
UN#:1993
Packing Group:

Computational Chemistry of [ 1185-55-3 ] Show Less

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 ?

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

27.69 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.26
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

0.67
Log Po/w (WLOGP)?

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

0.49
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.

-1.06
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

-1.34
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.2

Water Solubility

Log S (ESOL):?

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

-0.91
Solubility 16.8 mg/ml ; 0.123 mol/l
Class?

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

Very soluble
Log S (Ali)?

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

-0.83
Solubility 20.2 mg/ml ; 0.149 mol/l
Class?

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

Very 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

-0.72
Solubility 25.7 mg/ml ; 0.189 mol/l
Class?

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

Soluble

Pharmacokinetics

GI absorption?

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

High
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

No
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

No
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.

-6.66 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<1.0
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)

4.1

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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