Names | |
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Preferred IUPAC name 2,3-Dimethylbut-2-ene | |
Identifiers | |
3D model (JSmol) | |
ChemSpider | |
ECHA InfoCard | 100.008.422 |
EC Number |
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PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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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: | |
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.
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]
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]
In organic chemistry, a diene ; also diolefin, dy-OH-lə-fin) or alkadiene) is a covalent compound that contains two double bonds, usually among carbon atoms. They thus contain two alkene units, with the standard prefix di of systematic nomenclature. As a subunit of more complex molecules, dienes occur in naturally occurring and synthetic chemicals and are used in organic synthesis. Conjugated dienes are widely used as monomers in the polymer industry. Polyunsaturated fats are of interest to nutrition.
Cyclopentadiene is an organic compound with the formula C5H6. It is often abbreviated CpH because the cyclopentadienyl anion is abbreviated Cp−.
Terpyridine is a heterocyclic compound derived from pyridine. It is a white solid that is soluble in most organic solvents. The compound is mainly used as a ligand in coordination chemistry.
Rhodium(III) chloride refers to inorganic compounds with the formula RhCl3(H2O)n, where n varies from 0 to 3. These are diamagnetic solids featuring octahedral Rh(III) centres. Depending on the value of n, the material is either a dense brown solid or a soluble reddish salt. The soluble trihydrated (n = 3) salt is widely used to prepare compounds used in homogeneous catalysis, notably for the industrial production of acetic acid and hydroformylation.
Sodium bis(trimethylsilyl)amide is the organosilicon compound with the formula NaN(Si 3)2. This species, usually called NaHMDS, is a strong base used for deprotonation reactions or base-catalyzed reactions. Its advantages are that it is commercially available as a solid and it is soluble not only in ethers, such as THF or diethyl ether, but also in aromatic solvents, like benzene and toluene by virtue of the lipophilic TMS groups.
Cycloocta-1,5-diene is a cyclic hydrocarbon with the chemical formula C8H12, specifically [−(CH2)2−CH=CH−]2.
Titanocene dichloride is the organotitanium compound with the formula (η5-C5H5)2TiCl2, commonly abbreviated as Cp2TiCl2. This metallocene is a common reagent in organometallic and organic synthesis. It exists as a bright red solid that slowly hydrolyzes in air. It shows antitumour activity and was the first non-platinum complex to undergo clinical trials as a chemotherapy drug.
Tebbe's reagent is the organometallic compound with the formula (C5H5)2TiCH2ClAl(CH3)2. It is used in the methylidenation of carbonyl compounds, that is it converts organic compounds containing the R2C=O group into the related R2C=CH2 derivative. It is a red solid that is pyrophoric in the air, and thus is typically handled with air-free techniques. It was originally synthesized by Fred Tebbe at DuPont Central Research.
Organotitanium chemistry is the science of organotitanium compounds describing their physical properties, synthesis, and reactions. Organotitanium compounds in organometallic chemistry contain carbon-titanium chemical bonds. They are reagents in organic chemistry and are involved in major industrial processes.
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Organonickel chemistry is a branch of organometallic chemistry that deals with organic compounds featuring nickel-carbon bonds. They are used as a catalyst, as a building block in organic chemistry and in chemical vapor deposition. Organonickel compounds are also short-lived intermediates in organic reactions. The first organonickel compound was nickel tetracarbonyl Ni(CO)4, reported in 1890 and quickly applied in the Mond process for nickel purification. Organonickel complexes are prominent in numerous industrial processes including carbonylations, hydrocyanation, and the Shell higher olefin process.
Bis(cyclooctadiene)nickel(0) is the organonickel compound with the formula Ni(C8H12)2, also written Ni(cod)2. It is a diamagnetic coordination complex featuring tetrahedral nickel(0) bound to the alkene groups in two 1,5-cyclooctadiene ligands. This highly air-sensitive yellow solid is a common source of Ni(0) in chemical synthesis.
Organocobalt chemistry is the chemistry of organometallic compounds containing a carbon to cobalt chemical bond. Organocobalt compounds are involved in several organic reactions and the important biomolecule vitamin B12 has a cobalt-carbon bond. Many organocobalt compounds exhibit useful catalytic properties, the preeminent example being dicobalt octacarbonyl.
Organoiron chemistry is the chemistry of iron compounds containing a carbon-to-iron chemical bond. Organoiron compounds are relevant in organic synthesis as reagents such as iron pentacarbonyl, diiron nonacarbonyl and disodium tetracarbonylferrate. While iron adopts oxidation states from Fe(−II) through to Fe(VII), Fe(IV) is the highest established oxidation state for organoiron species. Although iron is generally less active in many catalytic applications, it is less expensive and "greener" than other metals. Organoiron compounds feature a wide range of ligands that support the Fe-C bond; as with other organometals, these supporting ligands prominently include phosphines, carbon monoxide, and cyclopentadienyl, but hard ligands such as amines are employed as well.
Organoruthenium chemistry is the chemistry of organometallic compounds containing a carbon to ruthenium chemical bond. Several organoruthenium catalysts are of commercial interest and organoruthenium compounds have been considered for cancer therapy. The chemistry has some stoichiometric similarities with organoiron chemistry, as iron is directly above ruthenium in group 8 of the periodic table. The most important reagents for the introduction of ruthenium are ruthenium(III) chloride and triruthenium dodecacarbonyl.
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Chlorobis(ethylene)rhodium dimer is an organorhodium compound with the formula Rh2Cl2(C2H4)4. It is a red-orange solid that is soluble in nonpolar organic solvents. The molecule consists of two bridging chloride ligands and four ethylene ligands. The ethylene ligands are labile and readily displaced even by other alkenes. A variety of homogeneous catalysts have been prepared from this complex.
Transition-metal allyl complexes are coordination complexes with allyl and its derivatives as ligands. Allyl is the radical with the connectivity CH2CHCH2, although as a ligand it is usually viewed as an allyl anion CH2=CH−CH2−, which is usually described as two equivalent resonance structures.
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