Trimethylsilyl cyclopentadiene

Trimethylsilyl cyclopentadiene
Names
	IUPAC name cyclopenta-2,4-dien-1-yl(trimethyl)silane
Identifiers
CAS Number	3559-74-8 ;
3D model (JSmol)	Interactive image;
ChemSpider	82435;
PubChem CID	91288;
	InChI InChI=1S/C8H14Si/c1-9(2,3)8-6-4-5-7-8/h4-8H,1-3H3 Key: VMFHCJPMKUTMMQ-UHFFFAOYSA-N;
	SMILES C[Si](C)(C)C1C=CC=C1;
Properties
Chemical formula	C8H14Si
Molar mass	138.285 g·mol−1
Appearance	Colorless liquid
Density	0.833 g/mL
Boiling point	138 to 140 °C (280 to 284 °F; 411 to 413 K)
Hazards
GHS pictograms
GHS Signal word	Warning
GHS hazard statements	H226, H315, H319, H335
GHS precautionary statements	P210, P233, P240, P241, P242, P243, P261, P264, P271, P280, P302+352, P303+361+353, P304+340, P305+351+338, P312, P321, P332+313, P337+313, P362, P370+378, P403+233, P403+235, 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 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.

Trimethylsilyl cyclopentadiene is an example of a molecule that undergoes rapid sigmatropic rearrangement. Observations of trimethylsilyl cyclopentadiene using gas phase NMR spectroscopy show that the protons on the ring are chemically equivalent, indicated by a single peak. This phenomenon, an example of fluxionality, is explained by the migration of the silyl group from carbon-to-carbon, thereby giving the appearance of equivalent CH signals.^[2]

Properties:^[3]

refractive index n20/D 1.471(lit.)

bp 138-140 °C(lit.)

density 0.833 g/mL at 25 °C(lit.)

storage temp. −20 °C

Synthesis

Trimethylsilyl cyclopentadiene is prepared by the reaction trimethylsilyl chloride (Me₃SiCl) with sodium cyclopentadienide (NaC₅H₅):^[4]^[5]

(CH₃)₃SiCl + NaC₅H₅ → C₅H₅Si(CH₃)₃ + NaCl

References

↑ ^1.0 ^1.1 "Trimethylsilyl cyclopentadiene". Sigma-Aldrich. http://www.sigmaaldrich.com/catalog/product/aldrich/257885?lang=en.
↑ Taha, A.N.; Moreno, P.O.; Lemaster, C.B.; Lemaster, C.L.; True, N.S. (2000). "1H NMR observation of trimethylsilyl migration in gas phase 5-trimethylsilylcyclopentadiene". Journal of Molecular Structure 553 (1–3): 37–42. doi:10.1016/S0022-2860(00)00549-4. Bibcode: 2000JMoSt.553...37T.
↑ "Trimethylsilyl cyclopentadiene, mixture of isomers 257885". https://www.sigmaaldrich.com/catalog/product/aldrich/257885.
↑ Seki, R.; Komatsu, S. (2011). "Preparation of (trialkylsilyl)cyclopentadienes containing almost no bis(trialkylsilyl)cyclopentadienes". Jpn. Kokai Tokkyo Koh..
↑ Francisco Palacios; Jesús M. de los Santos (2014). "5-(Trimethylsilyl)-1,3-cyclopentadiene". e-EROS Encyclopedia of Reagents for Organic Synthesis. pp. 1–8. doi:10.1002/047084289X.rn01739. ISBN 978-0-470-84289-8.

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Original source: https://en.wikipedia.org/wiki/Trimethylsilyl cyclopentadiene. Read more

[sigmaaldrich-1] 1.0 ^1.1 "Trimethylsilyl cyclopentadiene". Sigma-Aldrich. http://www.sigmaaldrich.com/catalog/product/aldrich/257885?lang=en.

[Taha-2] Taha, A.N.; Moreno, P.O.; Lemaster, C.B.; Lemaster, C.L.; True, N.S. (2000). "1H NMR observation of trimethylsilyl migration in gas phase 5-trimethylsilylcyclopentadiene". Journal of Molecular Structure 553 (1–3): 37–42. doi:10.1016/S0022-2860(00)00549-4. Bibcode: 2000JMoSt.553...37T.

[3] "Trimethylsilyl cyclopentadiene, mixture of isomers 257885". https://www.sigmaaldrich.com/catalog/product/aldrich/257885.

[Seki-4] Seki, R.; Komatsu, S. (2011). "Preparation of (trialkylsilyl)cyclopentadienes containing almost no bis(trialkylsilyl)cyclopentadienes". Jpn. Kokai Tokkyo Koh..

[5] Francisco Palacios; Jesús M. de los Santos (2014). "5-(Trimethylsilyl)-1,3-cyclopentadiene". e-EROS Encyclopedia of Reagents for Organic Synthesis. pp. 1–8. doi:10.1002/047084289X.rn01739. ISBN 978-0-470-84289-8.

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Trimethylsilyl cyclopentadiene

Topic: Chemistry

Synthesis

References