Names | |
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Preferred IUPAC name 1,1′-(Ethane-1,2-diyl)dibenzene | |
Other names 1,2-Diphenylethane Dibenzil Dibenzyl Dihydrostilbene sym-Diphenylethane | |
Identifiers | |
3D model (JSmol) | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.002.816 |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C14H14 | |
Molar mass | 182.266 g·mol−1 |
Appearance | Crystalline solid [1] |
Density | 0.9782 g/cm3 [1] |
Melting point | 52.0 to 52.5 °C (125.6 to 126.5 °F; 325.1 to 325.6 K) [1] |
Boiling point | 284 °C (543 °F; 557 K) [1] |
Insoluble | |
-126.8·10−6 cm3/mol | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Bibenzyl is the organic compound with the formula (C6H5CH2)2. It can be viewed as a derivative of ethane in which one phenyl group is bonded to each carbon atom. It is a colorless solid.
The compound is the product from the coupling of a pair of benzyl radicals. [2]
Bibenzyl forms the central core of some natural products like dihydrostilbenoids [3] and isoquinoline alkaloids. Marchantins are a family of bis(bibenzyl)-containing macrocycles. [4]
Samarium(II) iodide is an inorganic compound with the formula SmI2. When employed as a solution for organic synthesis, it is known as Kagan's reagent. SmI2 is a green solid and solutions are green as well. It is a strong one-electron reducing agent that is used in organic synthesis.
The Sonogashira reaction is a cross-coupling reaction used in organic synthesis to form carbon–carbon bonds. It employs a palladium catalyst as well as copper co-catalyst to form a carbon–carbon bond between a terminal alkyne and an aryl or vinyl halide.
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.
The Corey–House synthesis is an organic reaction that involves the reaction of a lithium diorganylcuprate with an organic halide or pseudohalide to form a new alkane, as well as an ill-defined organocopper species and lithium (pseudo)halide as byproducts.
Copper(I) iodide is the inorganic compound with the formula CuI. It is also known as cuprous iodide. It is useful in a variety of applications ranging from organic synthesis to cloud seeding.
In organic chemistry, cyclopropanation refers to any chemical process which generates cyclopropane rings. It is an important process in modern chemistry as many useful compounds bear this motif; for example pyrethroids and a number of quinolone antibiotics. However, the high ring strain present in cyclopropanes makes them challenging to produce and generally requires the use of highly reactive species, such as carbenes, ylids and carbanions. Many of the reactions proceed in a cheletropic manner.
The Negishi coupling is a widely employed transition metal catalyzed cross-coupling reaction. The reaction couples organic halides or triflates with organozinc compounds, forming carbon-carbon bonds (C-C) in the process. A palladium (0) species is generally utilized as the metal catalyst, though nickel is sometimes used. A variety of nickel catalysts in either Ni0 or NiII oxidation state can be employed in Negishi cross couplings such as Ni(PPh3)4, Ni(acac)2, Ni(COD)2 etc.
Organozinc chemistry is the study of the physical properties, synthesis, and reactions of organozinc compounds, which are organometallic compounds that contain carbon (C) to zinc (Zn) chemical bonds.
Organocopper chemistry is the study of the physical properties, reactions, and synthesis of organocopper compounds, which are organometallic compounds containing a carbon to copper chemical bond. They are reagents in organic chemistry.
Deoxygenation is a chemical reaction involving the removal of oxygen atoms from a molecule. The term also refers to the removal of molecular oxygen (O2) from gases and solvents, a step in air-free technique and gas purifiers. As applied to organic compounds, deoxygenation is a component of fuels production as well a type of reaction employed in organic synthesis, e.g. of pharmaceuticals.
The Castro–Stephens coupling is a cross coupling reaction between a copper(I) acetylide and an aryl halide in pyridine, forming a disubstituted alkyne and a copper(I) halide.
Organoiodine compounds are organic compounds that contain one or more carbon–iodine bonds. They occur widely in organic chemistry, but are relatively rare in nature. The thyroxine hormones are organoiodine compounds that are required for health and the reason for government-mandated iodization of salt.
In organic chemistry, a cross-coupling reaction is a reaction where two different fragments are joined. Cross-couplings are a subset of the more general coupling reactions. Often cross-coupling reactions require metal catalysts. One important reaction type is this:
Reductions with samarium(II) iodide involve the conversion of various classes of organic compounds into reduced products through the action of samarium(II) iodide, a mild one-electron reducing agent.
Riccardin C is a macrocyclic bis(bibenzyl). It is a secondary metabolite isolated from the Siberian cowslip subspecies Primula veris subsp. macrocalyx, in Reboulia hemisphaerica and in the Chinese liverwort Plagiochasma intermedium.
Dihydrostilbenoids (bibenzyls) are natural phenols formed from the dihydrostilbene (bibenzyl) backbone.
1,2-Diiodoethane is an organoiodine compound.
In organic chemistry, an ynone is an organic compound containing a ketone functional group and a C≡C triple bond. Many ynones are α,β-ynones, where the carbonyl and alkyne groups are conjugated. Capillin is a naturally occurring example. Some ynones are not conjugated.
The Mizoroki−Heck coupling of aryl halides and alkenes to form C(sp2)–C(sp2) bonds has become a staple transformation in organic synthesis, owing to its broad functional group compatibility and varied scope. In stark contrast, the palladium-catalyzed reductive Heck reaction has received considerably less attention, despite the fact that early reports of this reaction date back almost half a century. From the perspective of retrosynthetic logic, this transformation is highly enabling because it can forge alkyl–aryl linkages from widely available alkenes, rather than from the less accessible and/or more expensive alkyl halide or organometallic C(sp3) synthons that are needed in a classical aryl/alkyl cross-coupling.
Miyaura borylation, also known as the Miyaura borylation reaction, is a named reaction in organic chemistry that allows for the generation of boronates from vinyl or aryl halides with the cross-coupling of bis(pinacolato)diboron in basic conditions with a catalyst such as PdCl2(dppf). The resulting borylated products can be used as coupling partners for the Suzuki reaction.