Mesityl Bromide
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Mesityl Bromide
Mesityl bromide is an organic compound with the formula (CH3)3C6H2Br. It is a derivative of mesitylene (1,3,5-trimethylbenzene) with one ring H replaced by Br. The compound is a colorless oil. It is a standard electron-rich aryl halide In organic chemistry, an aryl halide (also known as haloarene) is an aromatic compound in which one or more hydrogen atoms, directly bonded to an aromatic ring are replaced by a halide. The haloarene are different from haloalkanes because they exhi ... substrate for cross coupling reactions. With magnesium it reacts to give the Grignard reagent, which is used in the preparation of tetramesityldiiron. It is prepared by the direct reaction of bromine with mesitylene:{{cite journal, journal=Org. Synth., year=1931, volume=11, page=24, doi=10.15227/orgsyn.011.0024, title=Bromomesitylene, author=Lee Irvin Smith :(CH3)3C6H3 + Br2 → (CH3)3C6H2Br + HBr References Bromoarenes Phenyl compounds ...
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Organic Compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The study of the properties, reactions, and syntheses of organic compounds comprise the discipline known as organic chemistry. For historical reasons, a few classes of carbon-containing compounds (e.g., carbonate salts and cyanide salts), along with a few other exceptions (e.g., carbon dioxide, hydrogen cyanide), are not classified as organic compounds and are considered inorganic. Other than those just named, little consensus exists among chemists on precisely which carbon-containing compounds are excluded, making any rigorous definition of an organic compound elusive. Although organic compounds make up only a small percentage of Earth's crust, they are of central importance because all known life is based on organic compounds. Living t ...
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Mesitylene
Mesitylene or 1,3,5-trimethylbenzene is a derivative of benzene with three methyl substituents positioned symmetrically around the ring. The other two isomeric trimethylbenzenes are 1,2,4-trimethylbenzene (pseudocumene) and 1,2,3-trimethylbenzene (hemimellitene). All three compounds have the formula C6H3(CH3)3, which is commonly abbreviated C6H3Me3. Mesitylene is a colorless liquid with sweet aromatic odor. It is a component of coal tar, which is its traditional source. It is a precursor to diverse fine chemicals. The mesityl group (Mes) is a substituent with the formula C6H2Me3 and is found in various other compounds. Preparation Mesitylene is prepared by transalkylation of xylene over solid acid catalyst:Karl Griesbaum, Arno Behr, Dieter Biedenkapp, Heinz-Werner Voges, Dorothea Garbe, Christian Paetz, Gerd Collin, Dieter Mayer, Hartmut Höke “Hydrocarbons” in Ullmann's Encyclopedia of Industrial Chemistry 2002 Wiley-VCH, Weinheim. . :2  C6H4(CH3)2 ⇌ C6H3( ...
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Aryl Halide
In organic chemistry, an aryl halide (also known as haloarene) is an aromatic compound in which one or more hydrogen atoms, directly bonded to an aromatic ring are replaced by a halide. The haloarene are different from haloalkanes because they exhibit many differences in methods of preparation and properties. The most important members are the aryl chlorides, but the class of compounds is so broad that there are many derivatives and applications. Preparation The two main preparatory routes to aryl halides are direct halogenation and via diazonium salts. Direct halogenation In the Friedel-Crafts halogenation, Lewis acids serve as catalysts. Many metal chlorides are used, examples include iron(III) chloride or aluminium chloride. The most important aryl halide, chlorobenzene is produced by this route. Monochlorination of benzene is always accompanied by formation of the dichlorobenzene derivatives. Arenes with electron donating groups react with halogens even in the absence of Le ...
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Cross Coupling Reaction
In organic chemistry, a cross-coupling reaction is a reaction where two fragments are joined together with the aid of a metal catalyst. In one important reaction type, a main group organometallic compound of the type R-M (R = organic fragment, M = main group center) reacts with an organic halide of the type R'-X with formation of a new carbon–carbon bond in the product R-R'. Cross-coupling reaction are a subset of coupling reactions. It is often used in arylations. Richard F. Heck, Ei-ichi Negishi, and Akira Suzuki were awarded the 2010 Nobel Prize in Chemistry for developing palladium-catalyzed coupling reactions. Mechanism The mechanism generally involves reductive elimination of the organic substituents R and R' on a metal complex of the type LnMR(R') (where L is some arbitrary spectator ligand). The crucial intermediate LnMR(R') is formed in a two step process from a low valence precursor Ln. The oxidative addition of an organic halide (RX) to LnM gives LnMR(X). Subse ...
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Grignard Reagent
A Grignard reagent or Grignard compound is a chemical compound with the general formula , where X is a halogen and R is an organic group, normally an alkyl or aryl. Two typical examples are methylmagnesium chloride and phenylmagnesium bromide . They are a subclass of the organomagnesium compounds. Grignard compounds are popular reagents in organic synthesis for creating new carbon-carbon bonds. For example, when reacted with another halogenated compound in the presence of a suitable catalyst, they typically yield and the magnesium halide as a byproduct; and the latter is insoluble in the solvents normally used. In this aspect, they are similar to organolithium reagents. Pure Grignard reagents are extremely reactive solids. They are normally handled as solutions in solvents such as diethyl ether or tetrahydrofuran; which are relatively stable as long as water is excluded. In such a medium, a Grignard reagent is invariably present as a complex with the magnesium atom conn ...
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Tetramesityldiiron
Tetramesityldiiron is an organoiron compound with the formula Fe2(C6H2(CH3)3)4. It is a red, air-sensitive solid that is used as a precursor to other iron complexes. It adopts a Molecular symmetry, centrosymmetric structure. The complex is a Lewis acid, forming monomeric adducts, e.g. Fe(C6H2(CH3)3)2pyridine2. The complex is prepared by treating ferrous halides with the Grignard reagent formed from mesityl bromide:{{cite book , doi=10.1002/9781119477822.ch4, title=Dimesityliron(II) Dimer and Dimesityldipyridineiron(II) (Mes = mesityl = C6H2-2,4,6-Me3) Crowded σ- and π-Bonded Metal Aryl Complexes, series=Inorganic Syntheses, last1=Martinez, first1=Gabriel Espinosa, last2=Killion, first2=Jack A., last3=Jackson, first3=Bailey J., last4=Fout, first4=Alison R., pages=50–55, year=2018, volume=36, s2cid=104749729 :2 FeCl2 + 4 BrMgC6H2(CH3)3 → Fe2(C6H2(CH3)3)4 + 2 MgBrCl References Organoiron compounds ...
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