Tetramethylethylene

Tetramethylethylene
Names
	IUPAC name 2,3-Dimethyl-2-butene
Identifiers
CAS Number	563-79-1;
3D model (JSmol)	Interactive image;
ChemSpider	10776;
ECHA InfoCard	100.008.422
EC Number	209-263-8;
PubChem CID	11250;
CompTox Dashboard (EPA)	DTXSID2060339 ;
	InChI InChI=1S/C6H12/c1-5(2)6(3)4/h1-4H3 Key: WGLLSSPDPJPLOR-UHFFFAOYSA-N;
	SMILES CC(=C(C)C)C;
Properties
Chemical formula	C6H12
Molar mass	84.162 g·mol−1
Appearance	colorless liquid
Density	0.7075 g/cm3 (at 20 °C)
Melting point	−74.6 °C (−102.3 °F; 198.6 K)
Boiling point	73.3 °C (163.9 °F; 346.4 K)
Hazards
GHS pictograms
GHS Signal word	Danger
GHS hazard statements	H225, H304
GHS precautionary statements	P210, P233, P240, P241, P242, P243, P280, P301+310, P303+361+353, P331, P370+378, 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

Tetramethylethylene is a hydrocarbon with the formula Me₂C=CMe₂ (Me = methyl). A colorless liquid, it is the simplest tetrasubstituted alkene.

Synthesis and reactions

It is prepared by base-catalyzed isomerization of 2,3-dimethyl-1-butene.[1]

Tetramethylethylene forms metal-alkene complexes with low-valent metals and reacts with diborane to give the monoalkyborane known as thexylborane.[2][3]

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References

Hattori, Hideshi (2001). "Solid base catalysts: Generation of basic sites and application to organic synthesis". Applied Catalysis A: General. 222 (1–2): 247–259. doi:10.1016/S0926-860X(01)00839-0.
Negishi, Ei-Ichi; Brown, Herbert C. (1974). "Thexylborane-A Highly Versatile Reagent for Organic Synthesis via Hydroboration". Synthesis. 1974 (2): 77–89. doi:10.1055/s-1974-23248.
Giordano, G.; Crabtree, R. H. (1990). "Di-μ-Chloro-Bis(η4 -1,5-Cyclooctadiene)-Dirhodium(I)". Inorganic Syntheses. 28. Event occurs at Di-μ-Chloro-Bis(η⁴-1,5-Cyclooctadiene)-Dirhodium(I). pp. 88–90. doi:10.1002/9780470132593.ch22. ISBN 9780470132593.

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[1] Hattori, Hideshi (2001). "Solid base catalysts: Generation of basic sites and application to organic synthesis". Applied Catalysis A: General. 222 (1–2): 247–259. doi:10.1016/S0926-860X(01)00839-0.

[2] Negishi, Ei-Ichi; Brown, Herbert C. (1974). "Thexylborane-A Highly Versatile Reagent for Organic Synthesis via Hydroboration". Synthesis. 1974 (2): 77–89. doi:10.1055/s-1974-23248.

[3] Giordano, G.; Crabtree, R. H. (1990). "Di-μ-Chloro-Bis(η4 -1,5-Cyclooctadiene)-Dirhodium(I)". Inorganic Syntheses. 28. Event occurs at Di-μ-Chloro-Bis(η⁴-1,5-Cyclooctadiene)-Dirhodium(I). pp. 88–90. doi:10.1002/9780470132593.ch22. ISBN 9780470132593.