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(Trimethylsilyl)methyl chloride

From Wikipedia, the free encyclopedia
(Trimethylsilyl)methyl chloride
Names
Other names
(Chloromethyl)trimethylsilane
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.017.326 Edit this at Wikidata
EC Number
  • 219-058-5
  • 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
Appearance colorless liquid
Density 0.886 g cm−3
Boiling point 97–98 °C (207–208 °F; 370–371 K)
Hazards
GHS labelling:[1]
GHS02: FlammableGHS07: Exclamation markGHS09: Environmental hazard
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).

(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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References

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  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.