| Identification | Back Directory | [Name]
ACETOXYMETHYLTRIETHOXYSILANE | [CAS]
5630-83-1 | [Synonyms]
riethoxysilylmethylacetate
ACETOXYMETHYLTRIETHOXYSILANE
triethoxysilylmethyl acetate
Methanol, 1-(triethoxysilyl)-, 1-acetate | [Molecular Formula]
C9H20O5Si | [MDL Number]
MFCD00270955 | [MOL File]
5630-83-1.mol | [Molecular Weight]
236.34 |
| Chemical Properties | Back Directory | [Boiling point ]
106 °C | [density ]
1.04 | [refractive index ]
1.4092 | [Fp ]
>60°C | [Specific Gravity]
1.04 | [Hydrolytic Sensitivity]
7: reacts slowly with moisture/water | [InChI]
InChI=1S/C9H20O5Si/c1-5-12-15(13-6-2,14-7-3)8-11-9(4)10/h5-8H2,1-4H3 | [InChIKey]
CSDVDSUBFYNSMC-UHFFFAOYSA-N | [SMILES]
C(OC(=O)C)[Si](OCC)(OCC)OCC |
| Hazard Information | Back Directory | [Chemical Properties]
Acetoxymethyltriethoxysilane hydrolyzes to form stable silanol solutions in neutral water, it reacts slowly with moisture/water.
| [Synthesis]
A 2 L 3-neck flask equipped with mechanical stirrer, pot thermometer and reflux condenser blanketed with nitrogen was charged with 1 l of acetonitrile, 1 g of 18-crown-6, 196 g (2 mole or a 100 % excess) of potassium acetate and 212.75 g (1 mole) of chloromethyltriethoxysilane. With agitation the mixture was brought to reflux for four hours and then the temperature reduced to just below reflux (pot temperature 80–84 ℃). The reaction progress was moni tored by GC. A full week of stirring was required to achieve about 90 % conversion. The reaction mixture was allowed to cool to room temperature. The supernatant was filtered from the salts through a Buchner funnel. The salts were washed with an additional 400 ml of acetonitrile and fil tered on a Buchner funnel. The combined supernatants were stripped at atmospheric pressure, allowing the pot temper ature to reach 120 ℃. The formation of new high boiling products observed by GC suggested that atmospheric distil lation of the product should not be attempted. The mixture was distilled at 15 mm Hg through a heated glass helix packed column. The overall recovered yield was 81 %. A fraction of 104 g assayed at 99+% by GC and was employed for physical property and spectroscopic evaluation.2
| [References]
[1] Arkles, B., King, K., & Pannell, K. (2013). Hydroxymethylsilanetriol – A Simple Analog of Silicic Acid. Silicon, 5 3, 187–197. https://doi.org/10.1007/s12633-013-9146-2
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