(Trimethylsilyl)methyl chloride

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(Trimethylsilyl)methyl chloride
TmsCH2Cl.svg
Names
Other names
(Chloromethyl)trimethylsilane
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.017.326 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 219-058-5
PubChem CID
  • InChI=1S/C4H11ClSi/c1-6(2,3)4-5/h4H2,1-3H3
    Key: OOCUOKHIVGWCTJ-UHFFFAOYSA-N
  • C[Si](C)(C)CCl
Properties
C4H11ClSi
Molar mass 122.67 g·mol−1
Appearancecolorless liquid
Density 0.886 g cm−3
Boiling point 97–98 °C (207–208 °F; 370–371 K)
Hazards
GHS labelling: [1]
GHS-pictogram-flamme.svg GHS-pictogram-exclam.svg GHS-pictogram-pollu.svg
Danger
H225, H315, H319, H335, H411
P210, P233, P240, P241, P242, P243, P261, P264, P271, P273, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P370+P378, P391, P403+P233, P403+P235, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

(Trimethylsilyl)methyl chloride is the organosilicon compound with the formula (CH3)3SiCH2Cl. A colorless, volatile liquid, it is an alkylating agent that is employed in organic synthesis, especially as a precursor to (trimethylsilyl)methyllithium. In the presence of triphenylphosphine, it olefinates benzophenones: [2]

(CH3)3SiCH2Cl + PPh3 + Ar2C=O → Ar2C=CH2 + OPPh3 + (CH3)3SiCl

See also

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Chromium(III) chloride Chemical compound

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Trimethylsilyl

A trimethylsilyl group (abbreviated TMS) is a functional group in organic chemistry. This group consists of three methyl groups bonded to a silicon atom [−Si(CH3)3], which is in turn bonded to the rest of a molecule. This structural group is characterized by chemical inertness and a large molecular volume, which makes it useful in a number of applications.

Chlorosilanes are a group of reactive, chlorine-containing chemical compounds, related to silane and used in many chemical processes. Each such chemical has at least one silicon-chlorine bond. Trichlorosilane is produced on the largest scale. The parent chlorosilane is silicon tetrachloride.

Trimethylsilyl chloride Chemical compound

Trimethylsilyl chloride, also known as chlorotrimethylsilane is an organosilicon compound (silyl halide), with the formula (CH3)3SiCl, often abbreviated Me3SiCl or TMSCl. It is a colourless volatile liquid that is stable in the absence of water. It is widely used in organic chemistry.

Organosilicon compound Organometallic compound containing carbon–silicon bonds

Organosilicon compounds are organometallic compounds containing carbon–silicon bonds. Organosilicon chemistry is the corresponding science of their preparation and properties. Most organosilicon compounds are similar to the ordinary organic compounds, being colourless, flammable, hydrophobic, and stable to air. Silicon carbide is an inorganic compound.

Trimethylsilyl cyanide Chemical compound

Trimethylsilyl cyanide is the chemical compound with the formula (CH3)3SiCN. This volatile liquid consists of a cyanide group, that is CN, attached to a trimethylsilyl group. The molecule is used in organic synthesis as the equivalent of hydrogen cyanide. It is prepared by the reaction of lithium cyanide and trimethylsilyl chloride:

Bis(trimethylsilyl)amine (also known as hexamethyldisilazane and HMDS) is an organosilicon compound with the molecular formula [(CH3)3Si]2NH. The molecule is a derivative of ammonia with trimethylsilyl groups in place of two hydrogen atoms. An electron diffraction study shows that silicon-nitrogen bond length (173.5 pm) and Si-N-Si bond angle (125.5°) to be similar to disilazane (in which methyl groups are replaced by hydrogen atoms) suggesting that steric factors are not a factor in regulating angles in this case. This colorless liquid is a reagent and a precursor to bases that are popular in organic synthesis and organometallic chemistry. Additionally, HMDS is also increasingly used as molecular precursor in chemical vapor deposition techniques to deposit silicon carbonitride thin films or coatings.

Hexamethyldisiloxane Chemical compound

Hexamethyldisiloxane (HMDSO) is an organosilicon compound with the formula O[Si(CH3)3]2. This volatile colourless liquid is used as a solvent and as a reagent in organic synthesis. It is prepared by the hydrolysis of trimethylsilyl chloride. The molecule is the protypical disiloxane and resembles a subunit of polydimethylsiloxane.

Bis(trimethylsilyl)sulfide Chemical compound

Bis(trimethylsilyl) sulfide is the chemical compound with the formula ((CH3)3Si)2S. Often abbreviated (tms)2S, this colourless, vile-smelling liquid is a useful aprotic source of "S2−" in chemical synthesis.

Trimethylsilyl azide Chemical compound

Trimethylsilyl azide ((CH3)3SiN3) is a chemical compound used as a reagent in organic chemistry.

Lithium bis(trimethylsilyl)amide Chemical compound

Lithium bis(trimethylsilyl)amide is a lithiated organosilicon compound with the formula LiN(Si 3)2. It is commonly abbreviated as LiHMDS 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.

Bis(trimethylsilyl)acetamide Chemical compound

Bis(trimethylsilyl)acetamide (BSA) is an organosilicon compound with the formula Me3SiNC(OSiMe3)Me (Me = CH3). It is a colorless liquid that is soluble in diverse organic solvents, but reacts rapidly with compounds, including solvents and moisture, containing OH and NH functional groups. It is used in analytical chemistry for the derivatisation of compounds in analysis to increase their volatility, e.g. for gas chromatography. It is also used to introduce the trimethylsilyl protecting group in organic synthesis. A related reagent is N,O-bis(trimethylsilyl)trifluoroacetamide (BSTFA).

Silylation is the introduction of one or more (usually) substituted silyl groups (R3Si) to a molecule. The process is the basis of organosilicon chemistry.

Bis(trimethylsilyl)acetylene Chemical compound

Bis(trimethylsilyl)acetylene (BTMSA) is an organosilicon compound with the formula Me3SiC≡CSiMe3 (Me = methyl). It is a colorless liquid that is soluble in organic solvents. This compound is used as a surrogate for acetylene.

Metal bis(trimethylsilyl)amides

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.

Trimethylsilyl cyclopentadiene Chemical compound

Trimethylsilyl cyclopentadiene is an organosilicon compound with the chemical formula C5H5Si(CH3)3. It exists as a colorless liquid. It is used in the synthesis of some metal cyclopentadienyl complexes and has attracted interest for its fluxional structure.

Tris(trimethylsilyl)phosphine Chemical compound

Tris(trimethylsilyl)phosphine is the organophosphorus compound with the formula P(SiMe3)3 (Me = methyl). It is a colorless liquid that ignites in air and hydrolyses readily.

<i>tert</i>-Butyldimethylsilyl chloride Chemical compound

tert-Butyldimethylsilyl chloride is an organosilicon compound with the formula (Me3C)Me2SiCl (Me = CH3). It is commonly abbreviated as TBSCl or TBDMSCl. It is a silane containing two methyl groups, a tert-butyl group, and a reactive chloride. It is a colorless or white solid that is soluble in many organic solvents but reacts with water and alcohols. The compound is used to protect alcohols in organic synthesis. Examples can be found in the Nicolaou taxol total synthesis.

(Trimethylsilyl)methyllithium Chemical compound

(Trimethylsilyl)methyllithium is classified both as an organolithium compound and an organosilicon compound. It has the empirical formula LiCH2Si(CH3)3, often abbreviated LiCH2tms. It crystallizes as the hexagonal prismatic hexamer [LiCH2tms]6, akin to some polymorphs of methyllithium. Many adducts have been characterized including the diethyl ether complexed cubane [Li43-CH2tms)4(Et2O)2] and [Li2(μ-CH2tms)2(tmeda)2].

References

  1. "Chloromethyltrimethylsilane". pubchem.ncbi.nlm.nih.gov. Retrieved 12 January 2022.
  2. Hamann, Lawrence G.; Jones, Todd K. (2001). "(Chloromethyl)trimethylsilane". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rc129. ISBN   0471936235.