Names | |
---|---|
Other names 2-ethylidene-5-norbornene | |
Identifiers | |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
Properties | |
C9H12 | |
Molar mass | 120.195 g·mol−1 |
Appearance | colorless liquid |
Density | 0.893 g/mL |
Melting point | −80 °C (−112 °F; 193 K) |
Boiling point | 146 °C (295 °F; 419 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Ethylidene norbornene (ENB) is an organic compound that consists of an ethylidene (CH3C(H)=) group attached to norbornene. It is a colorless liquid. The molecule consists of two sites of unsaturation. The compound consists of (E)- and (Z)-stereoisomers, but the mixtures are typically not separated.
It is prepared by isomerization of vinyl norbornene, which in turn is obtained by the Diels-Alder reaction of butadiene and cyclopentadiene. [1]
It is a monomer that used in the production of the commercial polymer EPDM. Only the ring alkene participates in the copolymerization. The exocyclic double bond (the ethylidene group) undergoes sulfur vulcanization.
Its LD50 (intravenous, rabbit) ranges from 0.09 (male rabbit) to 0.11 ml/kg (female). It is also a neurotoxin. [2]
Cyclopentadiene is an organic compound with the formula C5H6. It is often abbreviated CpH because the cyclopentadienyl anion is abbreviated Cp−.
In organic chemistry, an alicyclic compound contains one or more all-carbon rings which may be either saturated or unsaturated, but do not have aromatic character. Alicyclic compounds may have one or more aliphatic side chains attached.
The Heck reaction is the chemical reaction of an unsaturated halide with an alkene in the presence of a base and a palladium catalyst to form a substituted alkene. It is named after Tsutomu Mizoroki and Richard F. Heck. Heck was awarded the 2010 Nobel Prize in Chemistry, which he shared with Ei-ichi Negishi and Akira Suzuki, for the discovery and development of this reaction. This reaction was the first example of a carbon-carbon bond-forming reaction that followed a Pd(0)/Pd(II) catalytic cycle, the same catalytic cycle that is seen in other Pd(0)-catalyzed cross-coupling reactions. The Heck reaction is a way to substitute alkenes.
In organic chemistry, enols are a type of Functional group or intermediate in organic chemistry containing a group with the formula C=C(OH). The term enol is an abbreviation of alkenol, a portmanteau deriving from "-ene"/"alkene" and the "-ol". Many kinds of enols are known.
EPDM rubber is a type of synthetic rubber that is used in many applications.
In organic chemistry, olefin metathesis is an organic reaction that entails the redistribution of fragments of alkenes (olefins) by the scission and regeneration of carbon-carbon double bonds. Because of the relative simplicity of olefin metathesis, it often creates fewer undesired by-products and hazardous wastes than alternative organic reactions. For their elucidation of the reaction mechanism and their discovery of a variety of highly active catalysts, Yves Chauvin, Robert H. Grubbs, and Richard R. Schrock were collectively awarded the 2005 Nobel Prize in Chemistry.
Norbornene or norbornylene or norcamphene is a highly strained bridged cyclic hydrocarbon. It is a white solid with a pungent sour odor. The molecule consists of a cyclohexene ring with a methylene bridge between carbons 1 and 4. The molecule carries a double bond which induces significant ring strain and significant reactivity.
Palladium(II) acetate is a chemical compound of palladium described by the formula [Pd(O2CCH3)2]n, abbreviated [Pd(OAc)2]n. It is more reactive than the analogous platinum compound. Depending on the value of n, the compound is soluble in many organic solvents and is commonly used as a catalyst for organic reactions.
In organic chemistry, an anti-Bredt molecule is a bridged molecule with a double bond at the bridgehead. Bredt's rule is the empirical observation that such molecules only form in large ring systems. For example, two of the following norbornene isomers violate Bredt's rule, and are too unstable to prepare:
Methyl vinyl ketone (MVK, IUPAC name: butenone) is the organic compound with the formula CH3C(O)CH=CH2. It is a reactive compound classified as an enone, in fact the simplest example thereof. It is a colorless, flammable, highly toxic liquid with a pungent odor. It is soluble in water and polar organic solvents. It is a useful intermediate in the synthesis of other compounds.
[n]Radialenes are alicyclic organic compounds containing n cross-conjugated exocyclic double bonds. The double bonds are commonly alkene groups but those with a carbonyl (C=O) group are also called radialenes. For some members the unsubstituted parent radialenes are elusive but many substituted derivatives are known.
The molecular formula C9H12 may refer to:
Bisphenol A diglycidyl ether is an organic compound and is a liquid epoxy resin. The compound is a colorless viscous liquid. It is a key component of many epoxy resin formulations. Addition of further Bisphenol A and a catalyst and heat can produce Bisphenol A glycidyl ether epoxy resins of higher molecular weight that are solid.
Organoplatinum chemistry is the chemistry of organometallic compounds containing a carbon to platinum chemical bond, and the study of platinum as a catalyst in organic reactions. Organoplatinum compounds exist in oxidation state 0 to IV, with oxidation state II most abundant. The general order in bond strength is Pt-C (sp) > Pt-O > Pt-N > Pt-C (sp3). Organoplatinum and organopalladium chemistry are similar, but organoplatinum compounds are more stable and therefore less useful as catalysts.
Ethylidene diacetate is an organic compound with the formula (CH3CO2)2CHCH3. A colorless low-melting solid, it once served as a precursor to vinyl acetate.
In organosulfur chemistry, the thiol-ene reaction is an organic reaction between a thiol and an alkene to form a thioether. This reaction was first reported in 1905, but it gained prominence in the late 1990s and early 2000s for its feasibility and wide range of applications. This reaction is accepted as a click chemistry reaction given the reactions' high yield, stereoselectivity, high rate, and thermodynamic driving force.
Vinyllithium is an organolithium compound with the formula LiC2H3. A colorless or white solid, it is encountered mainly as a solution in tetrahydrofuran (THF). It is a reagent in synthesis of organic compounds, especially for vinylations.
Vinyl norbornene (VNB) is an organic compound that consists of a vinyl group attached to norbornene. It is a colorless liquid. The compound exists as endo and exo isomers, but these are not typically separated. It is an intermediate in the production of the commercial polymer EPDM. It is prepared by the Diels–Alder reaction of butadiene and cyclopentadiene.
α,β-Unsaturated carbonyl compounds are organic compounds with the general structure (O=CR)−Cα=Cβ−R. Such compounds include enones and enals, but also carboxylic acids and the corresponding esters and amides. In these compounds, the carbonyl group is conjugated with an alkene. Unlike the case for carbonyls without a flanking alkene group, α,β-unsaturated carbonyl compounds are susceptible to attack by nucleophiles at the β-carbon. This pattern of reactivity is called vinylogous. Examples of unsaturated carbonyls are acrolein (propenal), mesityl oxide, acrylic acid, and maleic acid. Unsaturated carbonyls can be prepared in the laboratory in an aldol reaction and in the Perkin reaction.
In organic chemistry, alkylidene is a general term for divalent functional groups of the form R2C=, where each R is an alkane or hydrogen. They can be considered the functional group corresponding to mono- or disubstituted divalent carbenes, or as the result of removing two hydrogen atoms from the same carbon atom in an alkane.