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Methyltrimethoxysilane

Methyltrimethoxysilane is an organosilicon compound with the formula CH3Si(OCH3)3. It is a colorless, free-flowing liquid. It is a crosslinker in the preparation of polysiloxane polymers.[1][2]

Methyltrimethoxysilane
Names
Preferred IUPAC name
Trimethoxy(methyl)silane
Other names
MTM, Trimethoxymethylsilane
Identifiers
  • 1185-55-3 Y
3D model (JSmol)
  • Interactive image
ChemSpider
  • 13803
ECHA InfoCard 100.013.350
  • 14456
UNII
  • 0HI0D71MCI Y
  • DTXSID3027370
  • InChI=1S/C4H12O3Si/c1-5-8(4,6-2)7-3/h1-4H3
    Key: BFXIKLCIZHOAAZ-UHFFFAOYSA-N
  • InChI=1/C4H12O3Si/c1-5-8(4,6-2)7-3/h1-4H3
    Key: BFXIKLCIZHOAAZ-UHFFFAOYAM
  • CO[Si](C)(OC)OC
Properties
C4H12O3Si
Molar mass 136.222 g·mol−1
Appearance Colorless liquid
Density 0.955 g/cm3
Boiling point 102–104 °C (216–219 °F; 375–377 K)
hydrolysis
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Preparation, structure and reactivity edit

Methyltrimethoxysilane is usually prepared from methyltrichlorosilane and methanol:

CH3SiCl3 + 3 CH3OH → CH3Si(OCH3)3 + 3 HCl

Alcoholysis of alkylchlorosilanes typically proceeds via an SN2 mechanism. Inversion of the configuration is favored during nucleophilic attack when displacing good leaving groups, such as chloride.[3] In contrast, displacement of poor leaving groups, such as alkoxide, retention is favored.[4]

Methyltrimethoxysilane is tetrahedral and is often described as sp3 hybridized. It has idealized C3v point symmetry.

Hydrolysis of MTM proceeds both under acidic and basic conditions. Under acid conditions, rates of successive hydrolyses for methyltrimethoxysilane decreases with each step. Under basic condition the opposite is true.[1]

See also edit

References edit

  1. ^ a b Brinker, C.J. (1988). "Hydrolysis and condensation of silicates: Effects on structure" (PDF). Journal of Non-Crystalline Solids. 100: 31. Bibcode:1988JNCS..100...31B. doi:10.1016/0022-3093(88)90005-1.
  2. ^ Kuroda, Kazuyuki; Shimojima, Atsushi; Kawahara, Kazufumi; Wakabayashi, Ryutaro; Tamura, Yasuhiro; Asakura, Yusuke; Kitahara, Masaki (2014). "Utilization of Alkoxysilyl Groups for the Creation of Structurally Controlled Siloxane-Based Nanomaterials". Chemistry of Materials. 26: 211. doi:10.1021/cm4023387.
  3. ^ Stephan, Pawlenko (1986). Organosilicon Chemistry. Berlin: Walter de Gruyter. ISBN 9780899252025.
  4. ^ Colvin, W. Ernest, Silicon in Organic Synthesis, Butterworth and Co Ltd, 1981.

methyltrimethoxysilane, organosilicon, compound, with, formula, ch3si, och3, colorless, free, flowing, liquid, crosslinker, preparation, polysiloxane, polymers, names, preferred, iupac, name, trimethoxy, methyl, silane, other, names, trimethoxymethylsilane, id. Methyltrimethoxysilane is an organosilicon compound with the formula CH3Si OCH3 3 It is a colorless free flowing liquid It is a crosslinker in the preparation of polysiloxane polymers 1 2 Methyltrimethoxysilane Names Preferred IUPAC name Trimethoxy methyl silane Other names MTM Trimethoxymethylsilane Identifiers CAS Number 1185 55 3 Y 3D model JSmol Interactive image ChemSpider 13803 ECHA InfoCard 100 013 350 PubChem CID 14456 UNII 0HI0D71MCI Y CompTox Dashboard EPA DTXSID3027370 InChI InChI 1S C4H12O3Si c1 5 8 4 6 2 7 3 h1 4H3Key BFXIKLCIZHOAAZ UHFFFAOYSA NInChI 1 C4H12O3Si c1 5 8 4 6 2 7 3 h1 4H3Key BFXIKLCIZHOAAZ UHFFFAOYAM SMILES CO Si C OC OC Properties Chemical formula C 4H 12O 3Si Molar mass 136 222 g mol 1 Appearance Colorless liquid Density 0 955 g cm3 Boiling point 102 104 C 216 219 F 375 377 K Solubility in water hydrolysis Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox referencesPreparation structure and reactivity editMethyltrimethoxysilane is usually prepared from methyltrichlorosilane and methanol CH3SiCl3 3 CH3OH CH3Si OCH3 3 3 HCl Alcoholysis of alkylchlorosilanes typically proceeds via an SN2 mechanism Inversion of the configuration is favored during nucleophilic attack when displacing good leaving groups such as chloride 3 In contrast displacement of poor leaving groups such as alkoxide retention is favored 4 Methyltrimethoxysilane is tetrahedral and is often described as sp3 hybridized It has idealized C3v point symmetry Hydrolysis of MTM proceeds both under acidic and basic conditions Under acid conditions rates of successive hydrolyses for methyltrimethoxysilane decreases with each step Under basic condition the opposite is true 1 See also editOctadecyltrimethoxysilaneReferences edit a b Brinker C J 1988 Hydrolysis and condensation of silicates Effects on structure PDF Journal of Non Crystalline Solids 100 31 Bibcode 1988JNCS 100 31B doi 10 1016 0022 3093 88 90005 1 Kuroda Kazuyuki Shimojima Atsushi Kawahara Kazufumi Wakabayashi Ryutaro Tamura Yasuhiro Asakura Yusuke Kitahara Masaki 2014 Utilization of Alkoxysilyl Groups for the Creation of Structurally Controlled Siloxane Based Nanomaterials Chemistry of Materials 26 211 doi 10 1021 cm4023387 Stephan Pawlenko 1986 Organosilicon Chemistry Berlin Walter de Gruyter ISBN 9780899252025 Colvin W Ernest Silicon in Organic Synthesis Butterworth and Co Ltd 1981 Retrieved from https en wikipedia org w index php title Methyltrimethoxysilane amp oldid 1096123505, wikipedia, wiki, book, books, library,

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