Trimethylsilyl cyclopentadiene

Names
IUPAC name

cyclopenta-2,4-dien-1-yl(trimethyl)silane

Identifiers

CAS Number

* 3559-74-8 N

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[1]
Boiling point |  138 to 140 °C (280 to 284 °F; 411 to 413 K)[1]
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. ↑ 1.0 1.1 "Trimethylsilyl cyclopentadiene". Sigma-Aldrich. http://www.sigmaaldrich.com/catalog/product/aldrich/257885?lang=en.
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.
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.

0.00

(0 votes)

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

|

Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:Trimethylsilyl_cyclopentadiene&oldid=813274"
*[CID]: Compound ID
*[H226]: Flammable liquid and vapour
*[H315]: Causes skin irritation
*[H319]: Causes serious eye irritation
*[H335]: May cause respiratory irritation
*[P210]: Keep away from heat/sparks/open flames/hot surfaces – No smoking
*[P233]: Keep container tightly closed
*[P240]: Ground/bond container and receiving equipment
*[P241]: Use explosion-proof electrical/ventilating/light/…/equipment
*[P242]: Use only non-sparking tools
*[P243]: Take precautionary measures against static discharge
*[P261]: Avoid breathing dust/fume/gas/mist/vapours/spray
*[P264]: Wash … thoroughly after handling
*[P271]: Use only outdoors or in a well-ventilated area
*[P280]: Wear protective gloves/protective clothing/eye protection/face protection
*[P302+352]: IF ON SKIN: Wash with soap and water
*[P303+361+353]: IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower
*[P304+340]: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
*[P305+351+338]: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do – continue rinsing
*[P312]: Call a POISON CENTER or doctor/physician if you feel unwell
*[P321]: Specific treatment (see … on this label)
*[P332+313]: If skin irritation occurs: Get medical advice/attention
*[P337+313]: Get medical advice/attention
*[P362]: Take off contaminated clothing and wash before reuse
*[P370+378]: In case of fire: Use … for extinction
*[P403+233]: Store in a well ventilated place. Keep container tightly closed
*[P403+235]: Store in a well ventilated place. Keep cool
*[P405]: Store locked up
*[P501]: Dispose of contents/container to …