1,2-Dimethoxy-1,1,2,2-Tetramethyldisilane

Catalog Number	ACM10124626-2
CAS Number	10124-62-6
Structure
Synonyms	1,2-Dimethoxy-1,1,2,2-tetramethyldisilane, 10124-62-6, AMTSi042, ACMC-1BNO8, 678163_ALDRICH, CTK3J7033, AG-D-07727, I14-91376, 1,2-Dimethoxy-1,1,2,2-tetramethyldisilane;1,2-Dimethoxytetramethyldisilane; sym-Dimethoxytetramethyldisilane
IUPAC Name	methoxy-[methoxy(dimethyl)silyl]-dimethylsilane
Molecular Weight	178.38 g/mol
Molecular Formula	C6H18O2Si2
Canonical SMILES	CO[Si](C)(C)[Si](C)(C)OC
InChI Key	CWGBHCIGKSXFED-UHFFFAOYSA-N
Boiling Point	138ºC at 760mmHg
Flash Point	27ºC
Purity	0.97
Density	0.859
Storage	Moisture Sensitive. Ambient temperatures.
Chemical Formula	C6H18O2Si2
Exact Mass	178.08500

Case Study

1,2-Dimethoxy-1,1,2,2-tetramethyldisilane for transition metal-catalyzed reactions of benzaldehyde and benzylideneamine with disilane

Williams, Neil A., Yuko Uchimaru, and Masato Tanaka. Dalton Transactions 2 (2003): 236-243.

Transition metal-catalyzed reactions of benzaldehyde and benzylideneamine with disilane were studied. Palladium phosphine complexes catalyzed the disilylation of the CO bonds in benzaldehyde and the CN bonds in benzylideneamine with 1,2-difluoro-1,1,2,2-tetramethyldisilane to form α-(fluorodimethylsilyl). When less active disilanes such as 1,2-dichloro- and 1,2-dimethoxy-1,1,2,2-tetramethyldisilane were used, the palladium phosphine complexes were less active and selective, leading to extensive side reactions, including the formation of 1, 2-disiloxy-1,2-diphenylethane. The reaction of benzaldehyde with 2,2-dimethyl-4,4,5,5-tetraphenyl-1,3-dioxa-2-silacyclopentane to produce benzophenone as a byproduct, such as 1,2-disiloxy-1,2-diphenylethane, seems to indicate the intermediate role of free radicals and silylene species. The same catalyst system was found to catalyze the intramolecular C-H activation of the ortho-silylation reaction of benzylideneamines with disilanes; mono- and bis-silylated products were obtained depending on the steric and electronic properties of the disilane, substrate, and catalyst used.
A mixture of 1,2-dimethoxy-1,1,2,2-tetramethyldisilane, benzaldehyde (0.5mmol, 51μl), Pt(dba) 0.005mmol; 2 mol% Pt relative to 1f, P(OCH)CEt (0.0166 mmol), decane (30 μl) as GC internal standard, and toluene (100 μl) were sealed in a reaction tube under nitrogen atmosphere. The tube was heated at 160°C for 20 hours. GLC analysis showed product formation. Analytically pure samples of fluorinated compounds were obtained by preparative GC.

Study of the reaction of silylene and acetylene using 1,2-Dimethoxy-1,1,2,2-Tetramethyldisilane

Barton, Thomas J., and John A. Kilgour. Journal of the American Chemical Society 98.24 (1976): 7746-7752.

To explain the mechanism of the reaction of silylene and acetylene to form 1,4-disilacyclohexa-2,5-diene (disilene) involving the Diels-Alder addition of acetylene to l,4-disilane. This new diene is probably produced by the ring opening of 3,4-disilacyclobutene. Pyrolysis experiments were performed using 1,2-Dimethoxy-1,1,2,2-Tetramethyldisilane. The experiments described show that under static pyrolysis conditions, disilene is produced by the reaction of silylene rather than disilene with acetylene. Although tetramethyldisilene does react with 2-butyne to form permethyldisilene, attempted crossover experiments ruled out the disilene dissociating into two silylene molecules. It was therefore concluded that the two mechanisms, silylene and disilene, merge in the middle to form disilene. The combined experiments do not exclude α-dimerization of the initially formed silacyclopropene.
Flow pyrolysis of 1,2-dimethoxy-1,1,2,2-tetramethyldisilane
0.162 g (0.91 mmol) 1,2-dimethoxy, 1,2-dimethoxy-1,1,2,2-tetramethyldisilane, 0.108 g (2.0 mmol) 2-butyne and 0.178 g (2.0 mmol) 3-hexyne were degassed in a tube. The tube was sealed under vacuum and heated to 225 °C for 18 h. The tube was opened and the products were analyzed and separated by gas chromatography.

Dimerization studies using 1,2-dimethoxy-1,1,2,2-tetramethyldisilane

Boganov, S. E., et al. Russian Chemical Bulletin 62 (2013): 622-633.

The concerted dimerization of 1-sila-cyclopropene-2-ene with different electronically effective substituents was investigated using the PBE/TZ2P method. In all cases, the corresponding reaction channels were found, which indicates the general characteristics of the reaction. The reaction barriers varied from moderately high to very low. The previous suggestion of the possibility that this process may occur during the reaction of silicene with alkynes at high temperatures was quantitatively confirmed for the first time. Using 2-dimethoxy-1,1,2,2-tetramethyldisilane with dimethylacetylene, the effect of the substituents on the barrier height and exothermicity of the dimerization of 1-sila-cyclopropene-2-ene was investigated. The β-dimerization of 1-sila-cyclopropene-2-ene is one of the few examples of bond metathesis in the absence of transition metal complexes.
Among the silicenes considered to participate in the high-temperature reaction of silicene with alkynes, tetramethylsilicene is the only stable compound. Its first synthesis was accomplished under conditions close to those used to prepare its dimer (i.e., octamethyl-1,4-disilacyclohexane-2,5-diene), specifically, by reaction of the dimethylsilylene generated from 1. ,2-Dimethoxy-1,1,2,2-tetramethyldisilane was reacted with dimethylacetylene in the gas phase at 600°C and reduced pressure (<0.1 Torr). This fact is another evidence that compound 1 was formed under the conditions used to prepare disilacyclohexane 2. However, tetramethylsilylene decomposed within 1 h at 105°C to form a polymer product of unknown structure.

Palladium-catalyzed synthesis of alkynes and 1,2-dimethoxy-1,1,2,2-tetramethyldisilane

Ansell, Melvyn B.; Navarro, Oscar; Spencer, John . Coordination Chemistry Reviews, 336(2017), 54-77.

The efficient stereoselective synthesis of polysubstituted alkenes or their precursors has been studied for a long time. They have attracted great interest due to their presence in various industries and fields of biologically important compounds. One of the most economical atomic routes to olefins is the transition metal-catalyzed heteroelement-element'π-insertion into alkynes.
The study used activated disilane, 1,2-dimethoxy-1,1,2,2-tetramethyldisilane in the bis(silylation) reaction of 1,4-diethynylbenzene to form the product. The product then ring-closes at each olefinic unit to form the corresponding disiloxane. Subsequent hydrogenation with hydrogen using Pd. carbon produces saturated monomers, tetrahydrofuran (THF) or therein undergoes ring-opening polymerization in the presence of catalytic amounts of tert-butylammonium.

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