Structure of 17096-07-0
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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| CAS No. : | 17096-07-0 |
| Formula : | C16H38O5Si4 |
| M.W : | 422.81 |
| SMILES Code : | CC(C(OCCC[Si](O[Si](C)(C)C)(O[Si](C)(C)C)O[Si](C)(C)C)=O)=C |
| MDL No. : | MFCD00053871 |
| InChI Key : | BESKSSIEODQWBP-UHFFFAOYSA-N |
| Pubchem ID : | 123371 |
| GHS Pictogram: |
|
| Signal Word: | Warning |
| Hazard Statements: | H315-H319-H335 |
| Precautionary Statements: | P261-P305+P351+P338 |
| Num. heavy atoms | 25 |
| Num. arom. heavy atoms | 0 |
| Fraction Csp3 | 0.81 |
| Num. rotatable bonds | 12 |
| Num. H-bond acceptors | 5.0 |
| Num. H-bond donors | 0.0 |
| Molar Refractivity | 114.56 |
| TPSA ? Topological Polar Surface Area: Calculated from |
53.99 Ų |
| Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
5.18 |
| Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
6.14 |
| Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
4.99 |
| Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.53 |
| Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
-1.65 |
| Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
3.24 |
| Log S (ESOL):? ESOL: Topological method implemented from |
-5.54 |
| Solubility | 0.00123 mg/ml ; 0.0000029 mol/l |
| Class? Solubility class: Log S scale |
Moderately soluble |
| Log S (Ali)? Ali: Topological method implemented from |
-7.06 |
| Solubility | 0.0000371 mg/ml ; 0.0000000878 mol/l |
| Class? Solubility class: Log S scale |
Poorly soluble |
| Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.64 |
| Solubility | 0.00964 mg/ml ; 0.0000228 mol/l |
| Class? Solubility class: Log S scale |
Moderately soluble |
| 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 |
Yes |
| P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
Yes |
| CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
No |
| CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
| CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
Yes |
| CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
| CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
| Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-4.52 cm/s |
| Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
| Ghose? Ghose filter: implemented from |
None |
| Veber? Veber (GSK) filter: implemented from |
1.0 |
| Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
| Muegge? Muegge (Bayer) filter: implemented from |
1.0 |
| Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
| PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
| Brenk? Structural Alert: implemented from |
2.0 alert: heavy_metal |
| Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<3.0 |
| Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
4.24 |
* 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.

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| In methanol; hexane; water; at 20℃; for 3h;Product distribution / selectivity; | 4. COMPARATIVE EXAMPLE 5-2; [00160] The same reaction procedures as in Comparative Example 5-1 were repeated except that trimethylchlorosilane was used in place of triethylchlorosilane. GC analysis of the obtained crude product revealed that 3-tris(trimethylsiloxy)silylpropyl methacrylate was obtained at a ratio of 69.8 % in terms of GC area % as a major product. | |
| With pyridine; In methanol; hexane; water; at 2 - 20℃; for 3h; | 12. Comparative Example 5-2 The same reaction procedures as in Comparative Example 5-1 were repeated except that trimethylchlorosilane was used in place of triethylchlorosilane. GC analysis of the obtained crude product revealed that 3-tris(trimethylsiloxy)silylpropyl methacrylate was obtained at a ratio of 69.8% in terms of GC area % as a major product. |
[ 107-46-0 ]
[ 2530-85-0 ]


[ 17096-07-0 ]| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 93.1% | Example 9 A 1000-ml four necked glass flask equipped with a reflux condenser, thermometer and stirrer was purged with nitrogen. The flask was charged with 406.0 g (2.5 mol) of hexamethyldisiloxane 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, 248.4 g (1.0 mol) of 3-methacryloxypropyltrimethoxysilane was added dropwise over 30 minutes, and stirring was continued at the temperature for one hour. At an internal temperature of 5-25C, 72.0 g (4.0 mol) of water was added dropwise over one hour. After the completion of dropwise addition, stirring was continued at 15-25C for 6.5 hours. The reaction solution was subjected to separatory operation to remove the aqueous layer. The organic layer was washed with water and separated again. The resulting 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, 3-MAPSi(OSiMe3)3/[3-MAPSi(OMe)(OSiMe3)2 + 3-MAPSi(OH) (OSiMe3)2] was 22.5. The total content of monomethoxy and monohydroxy compounds was 0.044 mol, as determined from the area percents by GC. While the organic layer was kept at a temperature of 20-25C, 24.5 g (0.25 mol) of conc. sulfuric acid was added dropwise over 15 minutes, and stirring was continued at the temperature for one 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, 3-MAPSi(OSiMe3)3/[3-MAPSi(OMe)(OSiMe3)2 + 3-MAPSi(OH)(OSiMe3)2] was 358.3. 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, 393.5 g (0.93 mol) of 3-methacryloxypropyltris(trimethylsiloxy)silane with a purity of 99.6% was collected as a fraction having a boiling point of 118.5-120.5C/0.2 kPa. The yield was 93.1%. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 83% | EXAMPLE 1 3-methacryloxypropyltris(trimethylsiloxy)silane In a three-neck flask, 75.4 g (0.47 mol) of hexamethyldisiloxane, 39.9 g (0.67 mol) of acetic acid, 8.7 g of sulfuric acid (conc.) (0.09 mol) and 0.5 g of a 10% solution of trifluoromethanesulfonic acid in acetic acid (0.0003 mol) are initially introduced and stirred at -15 C. to -5 C. At this temperature, 55.0 g (0.22 mol) of 3-methacryloxypropyltrimethoxysilane (Wacker GENIOSIL GF 31) are metered in over the course of one hour. The mixture is then heated to room temperature and after-stirred for 2 h. After separating off the acidic lower phase from the organic layer, the organic phase is analyzed by means of GC: the following are found (besides the readily volatile constituents): product 49.6 area %; monoorganoxy impurity CH2=CH(CH3)-COO-(CH2)3-Si(OSiMe3)2OMe (0.2 area %); monohydroxy impurity (CH2=CH(CH3)-COO-(CH2)3-Si(OSiMe3)2OH (0.5 area %) and 0.5 area % of the difunctional disiloxane (dimers) [CH2=CH(CH3)-COO-(CH2)3-Si(OSiMe3)2]O. To reduce the content of monohydroxysilane, at room temperature, 18.7 g (0.11 mol) of hexamethyldisilazane are added (1 h) and after-stirred for 1 h. Following the reaction and neutralization with HMN and removal by filtration of the formed salt, the following constituents are identified in the crude product in the GC besides readily volatile constituents: product (45.5 area %); monoorganoxy impurity CH2=CH(CH3)-COO-(CH2)3-Si(OSiMe3)2OMe (0.2 area %); monohydroxy impurity CH2=CH(CH3)-COO-(CH2)3-Si(OSiMe3)2OH (0.0 area %) and 0.3 area % of the difunctional disiloxane (dimers) [CH2=CH(CH3)-COO-(CH2)3-Si(OSiMe3)2]O. After distilling off the low-boiling components, the crude product has the following purities: product (97.8 area %); monoorganoxy impurity CH2=CH(CH3)-COO-(CH2)3-Si(OSiMe3)2OMe (0.2 area %); monohydroxy impurity CH2=CH(CH3)-COO-(CH2)3-Si(OSiMe3)2OH (0.0 area %) and 0.6 area % of the difunctional disiloxane (dimers) [CH2=CH(CH3)-COO-(CH2)3-Si(OSiMe3)2]O. Following distillation and fine filtration (filter candle), the product 3-methacryloxypropyltris(tri-methylsiloxy)silane is obtained in 83% yield, the following GC contents being obtained: product (99.5 area %); monoorganoxy impurity CH2=CH(CH3)-COO-(CH2)3-Si(OSiMe3)2OMe (0.2 area %); monohydroxy impurity CH2=CH(CH3)-COO-(CH2)3-Si(OSiMe3)2OH (0.0 area %) and 0.0 area % of the difunctional disiloxane (dimers) [CH2=CH(CH3)-COO-(CH2)3-Si(OSiMe3)2]O. | |
| 80% | EXAMPLE 13-methacryloxypropyltris(trimethylsiloxy)silaneIn a three-neck flask, 80.8 g (0.499 mol) of hexamethyldisiloxane, 39.9 g (0.67 mol) of acetic acid and 0.5 g of a 10% solution of trifluoromethanesulfonic acid in acetic acid (0.0003 mol) are initially introduced and heated to 45 C. with stirring. Then, over the course of one hour (at 45 C.), 55.0 g (0.22 mol) of 3-methacryloxypropyl-trimethoxysilane (WACKER GENIOSIL GF 31) are added and after-stirred for 1 h at 45 C. The crude product is analyzed by means of gas chromatography (GC). Besides the readily volatile constituents of the reaction mixture, the following GC contents are found: product (44.3 area %); monoorganoxy impurity CH2CH(CH3)-COO-(CH2)3-Si(OSiMe3)2OMe (1.1 area %); monohydroxy impurity CH2CH(CH3)-COO-(CH2)3Si(OSiMe3)2OH (0.6 area %), and 0.5 area % of the difunctional disiloxane (dimers) [CH2CH(CH3)-COO-(CH2)3-Si(OSiMe3)2]O.At 45 C., 13.1 g (0.167 mol) of acetyl chloride are added to the reaction mixture (over the course of 10 min), before the mixture is after-stirred for 10 min. At room temperature, an acidic phase is separated off from the organic layer before the reaction mixture is analyzed again by gas chromatography. The following are found: product (50.0 area %); monoorganoxy impurity CH2CH(CH3)-COO-(CH2)3Si(OSiMe3)2OMe (0.1 area %); monohydroxy impurity CH2CH(CH3)-COO-(CH2)3-Si(OSiMe3)2OH (0.5 area %) and 0.8 area % of the difunctional disiloxane (dimers) [CH2CH(CH3)-COO-(CH2)3-Si(OSiMe3)2]O.In order to eliminate/reduce the remaining content of monohydroxysilane impurity, 18 g (0.12 mol) of hexamethyl-disilazane are added, the reaction mixture being neutralized at the same time. After filtering off the formed salts, the reaction mixture is again analyzed by means of GC. The following are found: product (44.6 area %); monoorganoxy impurity CH2CH(CH3)-COO-(CH2)3-Si(OSiMe3)2OMe (0.1 area %); monohydroxy impurity CH2CH(CH3)-COO-(CH2)3-Si(OSiMe3)2OH (0.0 area %) and 0.8 area % of the difunctional disiloxane (dimers) [CH2CH(CH3)-COO-(CH2)3-Si(OSiMe3)2]O.After distilling off the volatile constituents, the product is distilled in vacuo and filtered off via a filter candle. The desired product is obtained in a yield of 80% and has a purity of 99.6 area % (contains 0.1 area % monoorganoxysilane). The specified monohydroxy and disiloxane impurities can no longer be detected. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 93.7% | With trifluorormethanesulfonic acid; 2,6-di-tert-butyl-4-methyl-phenol; at 80℃; for 1h;Dean-Stark; Inert atmosphere; | To a 500 mL three-necked flask equipped with a constant pressure funnel, magnetic stirrer, Dean-Stark tube and condenser, under nitrogen 124.18 g (0.5 mol) Methacryloxypropyltrimethoxysilane was added, 0.15 g of trifluoromethanesulfonic acid, 0.15 g of BHT was heated to 80 C and 198.35 g (1.5 mol) of acetoxytrimethylene was added dropwise to the reaction flask through a constant pressure funnel. As the dropwise addition progressed, most of the low boiling by-products were continuously distilled off and collected from the Dean-Stark tube side tube. After completion of the addition, stirring was continued for 1 hour. The reaction product was transferred to a separatory funnel and washed with water (100 mL) six times to obtain a neutral colorless transparent liquid. A small amount of low boiling substance was removed by rotary evaporation under reduced pressure to obtain 198.08 g of methacryloxypropyltris(trimethylsiloxy)silane in a yield of 93.7%. |
Tags: 17096-07-0 synthesis path| 17096-07-0 SDS| 17096-07-0 COA| 17096-07-0 purity| 17096-07-0 application| 17096-07-0 NMR| 17096-07-0 COA| 17096-07-0 structure
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| P101 | If medical advice is needed,have product container or label at hand. |
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| P221 | Take any precaution to avoid mixing with combustibles |
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| P270 | Do not eat, drink or smoke when using this product. |
| P271 | Use only outdoors or in a well-ventilated area. |
| P272 | Contaminated work clothing should not be allowed out of the workplace. |
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| P285 | In case of inadequate ventilation wear respiratory protection. |
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Response | |
| Code | Phrase |
| P301 | IF SWALLOWED: |
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| P307 | IF exposed: |
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| P378 | |
| P380 | Evacuate area. |
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| P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
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| P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
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| P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
| P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
| P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
| P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
| P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
| P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
| P370 + P376 | In case of fire: Stop leak if safe to Do so. |
| P370 + P378 | In case of fire: |
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| P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
| P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
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| P401 | |
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Physical hazards | |
| Code | Phrase |
| H200 | Unstable explosive |
| H201 | Explosive; mass explosion hazard |
| H202 | Explosive; severe projection hazard |
| H203 | Explosive; fire, blast or projection hazard |
| H204 | Fire or projection hazard |
| H205 | May mass explode in fire |
| H220 | Extremely flammable gas |
| H221 | Flammable gas |
| H222 | Extremely flammable aerosol |
| H223 | Flammable aerosol |
| H224 | Extremely flammable liquid and vapour |
| H225 | Highly flammable liquid and vapour |
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| H228 | Flammable solid |
| H229 | Pressurized container: may burst if heated |
| H230 | May react explosively even in the absence of air |
| H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
| H240 | Heating may cause an explosion |
| H241 | Heating may cause a fire or explosion |
| H242 | Heating may cause a fire |
| H250 | Catches fire spontaneously if exposed to air |
| H251 | Self-heating; may catch fire |
| H252 | Self-heating in large quantities; may catch fire |
| H260 | In contact with water releases flammable gases which may ignite spontaneously |
| H261 | In contact with water releases flammable gas |
| H270 | May cause or intensify fire; oxidizer |
| H271 | May cause fire or explosion; strong oxidizer |
| H272 | May intensify fire; oxidizer |
| H280 | Contains gas under pressure; may explode if heated |
| H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
| H290 | May be corrosive to metals |
Health hazards | |
| Code | Phrase |
| H300 | Fatal if swallowed |
| H301 | Toxic if swallowed |
| H302 | Harmful if swallowed |
| H303 | May be harmful if swallowed |
| H304 | May be fatal if swallowed and enters airways |
| H305 | May be harmful if swallowed and enters airways |
| H310 | Fatal in contact with skin |
| H311 | Toxic in contact with skin |
| H312 | Harmful in contact with skin |
| H313 | May be harmful in contact with skin |
| H314 | Causes severe skin burns and eye damage |
| H315 | Causes skin irritation |
| H316 | Causes mild skin irritation |
| H317 | May cause an allergic skin reaction |
| H318 | Causes serious eye damage |
| H319 | Causes serious eye irritation |
| H320 | Causes eye irritation |
| H330 | Fatal if inhaled |
| H331 | Toxic if inhaled |
| H332 | Harmful if inhaled |
| H333 | May be harmful if inhaled |
| H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
| H335 | May cause respiratory irritation |
| H336 | May cause drowsiness or dizziness |
| H340 | May cause genetic defects |
| H341 | Suspected of causing genetic defects |
| H350 | May cause cancer |
| H351 | Suspected of causing cancer |
| H360 | May damage fertility or the unborn child |
| H361 | Suspected of damaging fertility or the unborn child |
| H361d | Suspected of damaging the unborn child |
| H362 | May cause harm to breast-fed children |
| H370 | Causes damage to organs |
| H371 | May cause damage to organs |
| H372 | Causes damage to organs through prolonged or repeated exposure |
| H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
| Code | Phrase |
| H400 | Very toxic to aquatic life |
| H401 | Toxic to aquatic life |
| H402 | Harmful to aquatic life |
| H410 | Very toxic to aquatic life with long-lasting effects |
| H411 | Toxic to aquatic life with long-lasting effects |
| H412 | Harmful to aquatic life with long-lasting effects |
| H413 | May cause long-lasting harmful effects to aquatic life |
| H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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