Tetramethylethylene
Jump to navigation
Jump to search
| Names | |
|---|---|
| Preferred IUPAC name
2,3-Dimethylbut-2-ene | |
| Identifiers | |
3D model (JSmol)
|
|
| ChemSpider | |
| ECHA InfoCard | Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value). Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value).Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value). |
| EC Number |
|
| E number | Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value). |
PubChem CID
|
|
| UNII | |
CompTox Dashboard (EPA)
|
|
| |
| |
| Properties | |
| C6H12 | |
| Molar mass | 84.162 g·mol−1 |
| Appearance | colorless liquid |
| Density | 0.7075 g/cm3 (20 °C) |
| Melting point | −74.6 °C (−102.3 °F; 198.6 K) |
| Boiling point | 73.3 °C (163.9 °F; 346.4 K) |
| Critical point (T, P) | 521.0(9) K, 3.4(1) MPa[1] |
| insoluble | |
| Solubility | soluble in ethanol, ether, acetone, chloroform[1] |
| −65.9×10−6 cm3·mol−1[1] | |
Refractive index (nD)
|
1.4122 (20 °C)[1] |
| Thermochemistry[1] | |
Heat capacity (C)
|
174.7 J·mol−1·K−1 |
Std molar
entropy (S⦵298) |
270.2 J·mol−1·K−1 |
Std enthalpy of
formation (ΔfH⦵298) |
−101.4 kJ·mol−1 (liquid) −68.1 kJ·mol−1 (gas) |
Enthalpy of fusion (ΔfH⦵fus)
|
6.45 kJ·mol−1 (at melting point) |
Enthalpy of vaporization (ΔfHvap)
|
32.51 kJ·mol−1 (25 °C) 29.64 kJ·mol−1 (at boiling point) |
| Hazards | |
| GHS labelling: | |
| GHS02: FlammableGHS08: Health hazard | |
| Danger | |
| H225, H304 | |
| P210, P233, P240, P241, P242, P243, P280, P301+P310, P303+P361+P353, P331, P370+P378, P403+P235, P405, P501 | |
| Flash point | −8 °C |
| 401 °C[1] | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
| |
Tetramethylethylene is a hydrocarbon with the formula Me2C=CMe2 (Me = methyl). A colorless liquid, it is the simplest tetrasubstituted alkene.
Synthesis
[edit | edit source]It can be prepared by base-catalyzed isomerization of 2,3-dimethyl-1-butene.[2] Another route involves direct dimerization of propylene.[3] It can also be produced by photolysis of tetramethylcyclobutane-1,3-dione.[4]
Reactions
[edit | edit source]Tetramethylethylene forms metal-alkene complexes with low-valent metals and reacts with diborane to give the monoalkyborane known as thexylborane.[5][6]
Oxidation gives pinacol.
It is a precursor to the herbicide fenpropathrin.[3]
References
[edit | edit source]- ^ a b c d e f Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
- ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
- ^ a b Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
- ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
- ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
- ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).