1,3,5,7-Tetramethyl-1,3,5,7-tetrasilaadamantane

Last updated
1,3,5,7-Tetramethyl-1,3,5,7-tetrasilaadamantane
1,3,5,7-tetramethyl-1,3,5,7-tetrasilaadamantane.svg
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/C10H24Si4/c1-11-5-12(2)8-13(3,6-11)10-14(4,7-11)9-12/h5-10H2,1-4H3
    Key: XMNIPURNPMVXKW-UHFFFAOYSA-N
  • C[Si]12C[Si]3(C[Si](C1)(C[Si](C2)(C3)C)C)C
Properties
C6H24Si4
Molar mass 208.598 g·mol−1
Appearancecolorless solid
Melting point 244 °C (471 °F; 517 K) [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

1,3,5,7-Tetramethyl-1,3,5,7-tetrasilaadamantane is the organosilicon compound with the formula (CH2)6(SiCH3)4. It is a colorless solid that is soluble in organic solvents. The compound is one of the iconic carbosilanes, featuring alternating −Si−C−Si−C− linkages. [2] Otherwise it can be described as a diamondoid cluster. It arises as one of many products from the pyrolysis of tetramethylsilane. A more efficient route involves the reaction of the cyclic carbosilane (CH2Si(CH3)2)3 (1,1,3,3,5,5-hexamethyl-1,3,5-trisilacyclohexane) with aluminium tribromide. [3]

Carbosilanes are known for several diamondoid structures. Heptasila diadamantane.svg
Carbosilanes are known for several diamondoid structures.

Related Research Articles

Pyruvic acid (IUPAC name: 2-oxopropanoic acid, also called acetoic acid) (CH3COCOOH) is the simplest of the alpha-keto acids, with a carboxylic acid and a ketone functional group. Pyruvate, the conjugate base, CH3COCOO, is an intermediate in several metabolic pathways throughout the cell.

In organic chemistry, an alkyl group is an alkane missing one hydrogen. The term alkyl is intentionally unspecific to include many possible substitutions. An acyclic alkyl has the general formula of CnH2n+1. A cycloalkyl group is derived from a cycloalkane by removal of a hydrogen atom from a ring and has the general formula CnH2n−1. Typically an alkyl is a part of a larger molecule. In structural formulae, the symbol R is used to designate a generic (unspecified) alkyl group. The smallest alkyl group is methyl, with the formula CH3.

<span class="mw-page-title-main">Organotin chemistry</span> Branch of organic chemistry

Organotin chemistry is the scientific study of the synthesis and properties of organotin compounds or stannanes, which are organometallic compounds containing tin carbon bonds. The first organotin compound was diethyltin diiodide, discovered by Edward Frankland in 1849. The area grew rapidly in the 1900s, especially after the discovery of the Grignard reagents, which are useful for producing Sn–C bonds. The area remains rich with many applications in industry and continuing activity in the research laboratory.

<span class="mw-page-title-main">Siloxane</span> Si–O–Si chemical bond

A siloxane is a functional group in organosilicon chemistry with the Si−O−Si linkage. The parent siloxanes include the oligomeric and polymeric hydrides with the formulae H(OSiH2)nOH and (OSiH2)n. Siloxanes also include branched compounds, the defining feature of which is that each pair of silicon centres is separated by one oxygen (O) atom. The siloxane functional group forms the backbone of silicones, the premier example of which is polydimethylsiloxane (PDMS). The functional group R3SiO− (where the three Rs may be different) is called siloxy. Siloxanes are manmade and have many commercial and industrial applications because of the compounds’ hydrophobicity, low thermal conductivity, and high flexibility.

<span class="mw-page-title-main">Tetramethylsilane</span> Chemical compound

Tetramethylsilane (abbreviated as TMS) is the organosilicon compound with the formula Si(CH3)4. It is the simplest tetraorganosilane. Like all silanes, the TMS framework is tetrahedral. TMS is a building block in organometallic chemistry but also finds use in diverse niche applications.

<span class="mw-page-title-main">Organosilicon chemistry</span> Organometallic compound containing carbon–silicon bonds

Organosilicon chemistry is the study of organometallic compounds containing carbon–silicon bonds, to which they are called organosilicon compounds. Most organosilicon compounds are similar to the ordinary organic compounds, being colourless, flammable, hydrophobic, and stable to air. Silicon carbide is an inorganic compound.

Hydrosilylation, also called catalytic hydrosilation, describes the addition of Si-H bonds across unsaturated bonds. Ordinarily the reaction is conducted catalytically and usually the substrates are unsaturated organic compounds. Alkenes and alkynes give alkyl and vinyl silanes; aldehydes and ketones give silyl ethers. Hydrosilylation has been called the "most important application of platinum in homogeneous catalysis."

<span class="mw-page-title-main">Organoaluminium chemistry</span>

Organoaluminium chemistry is the study of compounds containing bonds between carbon and aluminium. It is one of the major themes within organometallic chemistry. Illustrative organoaluminium compounds are the dimer trimethylaluminium, the monomer triisobutylaluminium, and the titanium-aluminium compound called Tebbe's reagent. The behavior of organoaluminium compounds can be understood in terms of the polarity of the C−Al bond and the high Lewis acidity of the three-coordinated species. Industrially, these compounds are mainly used for the production of polyolefins.

<span class="mw-page-title-main">Lithium bis(trimethylsilyl)amide</span> Chemical compound

Lithium bis(trimethylsilyl)amide is a lithiated organosilicon compound with the formula LiN(Si(CH3)3)2. It is commonly abbreviated as LiHMDS or Li(HMDS) (lithium hexamethyldisilazide - a reference to its conjugate acid HMDS) and is primarily used as a strong non-nucleophilic base and as a ligand. Like many lithium reagents, it has a tendency to aggregate and will form a cyclic trimer in the absence of coordinating species.

Trimethylsilanol (TMS) is an organosilicon compound with the formula (CH3)3SiOH. The Si centre bears three methyl groups and one hydroxyl group. It is a colourless volatile liquid.

In chemical nomenclature, a preferred IUPAC name (PIN) is a unique name, assigned to a chemical substance and preferred among the possible names generated by IUPAC nomenclature. The "preferred IUPAC nomenclature" provides a set of rules for choosing between multiple possibilities in situations where it is important to decide on a unique name. It is intended for use in legal and regulatory situations.

<span class="mw-page-title-main">Disilyne</span> Chemical compound

Disilyne is a silicon hydride with the formula Si
2
H
2
. Several isomers are possible, but none are sufficiently stable to be of practical value. Substituted disilynes contain a formal silicon–silicon triple bond and as such are sometimes written R2Si2 (where R is a substituent group). They are the silicon analogues of alkynes.

<span class="mw-page-title-main">Organobismuth chemistry</span>

Organobismuth chemistry is the chemistry of organometallic compounds containing a carbon to bismuth chemical bond. Applications are few. The main bismuth oxidation states are Bi(III) and Bi(V) as in all higher group 15 elements. The energy of a bond to carbon in this group decreases in the order P > As > Sb > Bi. The first reported use of bismuth in organic chemistry was in oxidation of alcohols by Frederick Challenger in 1934 (using Ph3Bi(OH)2). Knowledge about methylated species of bismuth in environmental and biological media is limited.

Organorhenium chemistry describes the compounds with Re−C bonds. Because rhenium is a rare element, relatively few applications exist, but the area has been a rich source of concepts and a few useful catalysts.

<span class="mw-page-title-main">Glutarimide</span> Chemical compound

Glutarimide is the organic compound with the formula (CH2)3(CO)2NH. It is a white solid. The compound forms upon dehydration of the amide of glutaric acid.

<span class="mw-page-title-main">Metal bis(trimethylsilyl)amides</span>

Metal bis(trimethylsilyl)amides are coordination complexes composed of a cationic metal with anionic bis(trimethylsilyl)amide ligands and are part of a broader category of metal amides.

Silanes refers to diverse organosilicon charge-neutral compounds with the formula SiR
4
. The R substituents can any combination of organic or inorganic groups. Most silanes contain Si-C bonds, and are discussed under organosilicon compounds. Some contain Si-H bonds and are discussed under hydrosilanes.

Hydroxymethylation is a chemical reaction that installs the CH2OH group. The transformation can be implemented in many ways and applies to both industrial and biochemical processes.

<span class="mw-page-title-main">Organothorium chemistry</span> Study of the carbon-thorium bond

Organothorium chemistry describes the synthesis and properties of chemical compounds containing a carbon to thorium chemical bond.

<span class="mw-page-title-main">Carbosilanes</span> Class of chemical compounds

Carbosilanes are organosilicon compounds where the structures feature alternating silicon and carbon atoms, i.e., −Si−C−Si−C− linkages. They represent molecular analogues of silicon carbide. The compounds exploit the tendency of both carbon and silicon to form tetrahedral structures. The inventory of carbosilanes is large.

References

  1. Fritz, G.; Haase, R.; Kummer, D. (1969). "Bildung siliciumhaltiger Verbindungen, XXVII. Carbosilane mit vier Si-Atomen". Zeitschrift für Anorganische und Allgemeine Chemie. 365 (1–2): 1–13. doi:10.1002/zaac.19693650102.
  2. Fritz, Gerhard; Matern, Eberhard (1986). Carbosilanes. doi:10.1007/978-3-642-70800-8. ISBN   978-3-642-70802-2.
  3. Frye, Cecil L.; Klosowski, Jerome M.; Weyenberg, Donald R. (1970). "1,3,5,7-Tetrasilaadamantanes. Facile synthesis via catalyzed ligand redistribution". Journal of the American Chemical Society. 92 (21): 6379–6380. doi:10.1021/ja00724a069.