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Bromoiodobenzene
1-Bromo-4-iodobenzene is a mixed aryl halide (aryl bromide and aryl iodide) with the formula BrC6H4I. Preparation In one laboratory route to 1-bromo-4-iodobenzene, 4-bromoaniline is treated with concentrated sulfuric acid and sodium nitrite to form the diazonium salt, which is then treated with potassium iodide to form 1-bromo-4-iodobenzene. Reactions Since aryl iodides are more reactive than aryl bromides in the Sonogashira coupling, the iodine end of 1-bromo-4-iodobenzene can be selectively coupled to a terminal acetylene while leaving the bromine end unreacted, by running the reaction at room temperature. For example, two equivalents of 1-bromo-4-iodobenzene can couple to trimethylsilylacetylene in a room temperature symmetrical Sonogashira coupling (with TMSA being deprotected to acetylene ''in-situ'') to form bis(4-bromophenyl)acetylene. : See also *Bromobenzene *Iodobenzene *Bromochlorobenzene Bromochlorobenzenes are mixed aryl halides (aryl chloride and aryl bromide) co ...
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Bromochlorobenzene
Bromochlorobenzenes are mixed aryl halides (aryl chloride and aryl bromide) consisting bromine and chlorine as substituents on a benzene ring. All three have been synthesized by various routes: * 1-Bromo-2-chlorobenzene: from 2-chloroaniline, via diazotization followed by a Sandmeyer reaction * 1-Bromo-3-chlorobenzene: by (3-chlorophenyl)trimethylgermanium by electrophilic substitution * 1-Bromo-4-chlorobenzene: **From a derivative of (4-bromophenyl)silane using N-Bromosuccinimide, ''N''-bromosuccinimide **From 4-Chlorophenol, 4-chlorophenol using triphenylphosphine dibromide or phenylphosphorus tetrachloride See also *Bromoiodobenzene References

{{Authority control Chlorobenzene derivatives Bromobenzene derivatives Mixed halobenzenes Multiple compounds, tabular, C ...
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ChemSpider
ChemSpider is a freely accessible online chemical database, database of chemicals owned by the Royal Society of Chemistry. It contains information on more than 100 million molecules from over 270 data sources, each of them receiving a unique identifier called ChemSpider Identifier. Sources The database sources include: Professional databases * EPA DSSTox * Food and Drug Administration (United States), U.S. Food and Drug Administration (FDA) * Human Metabolome Database * Journal of Heterocyclic Chemistry * KEGG * KUMGM * LeadScope * LIPID MAPS, LipidMAPS * Marinlit * MDPI * MICAD * MLSMR * MMDB * MOLI * MTDP * Nanogen * Nature Chemical Biology * NCGC * NIAID * National Institutes of Health (NIH) * NINDS Approved Drug Screening Program * NIST * NIST Chemistry WebBook * NMMLSC * NMRShiftDB * PANACHE * PCMD * PDSP * Peptides (journal), Peptides * Prous Science Drugs of the Future * QSAR * R&D Chemicals * San Diego Center for Chemical Genomics * SGCOxCompounds, SGCStoCompounds ...
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Chem
Chem may refer to: *Chemistry *Chemical * ''Chem'' (journal), a scientific journal published by Cell Press *Post apocalyptic slang for "drugs", medicinal or otherwise in the Fallout video game series. In Ancient Egyptian usage: * ''Khem'' (also spelt ''Chem''), the Egyptian word for "black" *Min (god), in the past erroneously named ''Khem'' CHEM may refer to : *A metabolic panel: for instance, CHEM-7, which is the basic metabolic panel * CHEM-DT, a Canadian television channel See also * Chemo (other) * Kem (other) *Kemi Kemi (; ; ; ) is a cities of Finland, town and municipalities of Finland, municipality of Finland. It is located approximately from the city of Tornio and the Finland–Sweden border, Swedish border. The distance to Oulu is to the south and t ...
, a place in Finland {{disambig ...
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Bromobenzene Derivatives
Bromobenzene is an aryl bromide and the simplest of the bromobenzenes, consisting of a benzene ring substituted with one bromine atom. Its chemical formula is . It is a colourless liquid although older samples can appear yellow. It is a reagent in organic synthesis. Synthesis and reactions Bromobenzene is prepared by the action of bromine on benzene in the presence of Lewis acid catalysts such as aluminium chloride or ferric bromide. Bromobenzene is used to introduce a phenyl group into other compounds. One method involves its conversion to the Grignard reagent, phenylmagnesium bromide. This reagent can be used, e.g. in the reaction with carbon dioxide to prepare benzoic acid. Other methods involve palladium-catalyzed coupling reactions, such as the Suzuki reaction. Bromobenzene is used as a precursor in the manufacture of phencyclidine Phencyclidine or phenylcyclohexyl piperidine (PCP), also known in its use as a street drug as angel dust among other names, is a dis ...
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Iodobenzene
Iodobenzene is an aryl iodide and the simplest of the iodobenzenes, consisting of a benzene ring substituted with one iodine atom. Its chemical formula is . It is useful as a synthetic intermediate in organic chemistry. It is a volatile colorless liquid, although aged samples appear yellowish. Preparation Iodobenzene is commercially available, or it can be prepared in the laboratory from aniline via the diazotization reaction. In the first step, the amine functional group is diazotized with hydrochloric acid and sodium nitrite. Potassium iodide is added to the resultant phenyldiazonium chloride, causing nitrogen gas to evolve. The product is separated by steam distillation. : Alternatively, it can be produced by refluxing iodine and nitric acid with benzene. Reactions Since the C–I bond is weaker than C–Br or C–Cl, iodobenzene is more reactive than bromobenzene or chlorobenzene. Iodobenzene reacts readily with magnesium to form the Grignard reagent, phenylmagnesium i ...
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Bromobenzene
Bromobenzene is an aryl bromide and the simplest of the bromobenzenes, consisting of a benzene ring substituted with one bromine atom. Its chemical formula is . It is a colourless liquid although older samples can appear yellow. It is a reagent in organic synthesis. Synthesis and reactions Bromobenzene is prepared by the action of bromine on benzene in the presence of Lewis acid catalysts such as aluminium chloride or ferric bromide. Bromobenzene is used to introduce a phenyl group into other compounds. One method involves its conversion to the Grignard reagent, phenylmagnesium bromide. This reagent can be used, e.g. in the reaction with carbon dioxide to prepare benzoic acid. Other methods involve palladium-catalyzed coupling reactions, such as the Suzuki reaction. Bromobenzene is used as a precursor in the manufacture of phencyclidine Phencyclidine or phenylcyclohexyl piperidine (PCP), also known in its use as a street drug as angel dust among other names, is a dis ...
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Symmetrical Sonogashira 1-bromo-4-iodobenzene
Symmetry () in everyday life refers to a sense of harmonious and beautiful proportion and balance. In mathematics, the term has a more precise definition and is usually used to refer to an object that is invariant under some transformations, such as translation, reflection, rotation, or scaling. Although these two meanings of the word can sometimes be told apart, they are intricately related, and hence are discussed together in this article. Mathematical symmetry may be observed with respect to the passage of time; as a spatial relationship; through geometric transformations; through other kinds of functional transformations; and as an aspect of abstract objects, including theoretic models, language, and music. This article describes symmetry from three perspectives: in mathematics, including geometry, the most familiar type of symmetry for many people; in science and nature; and in the arts, covering architecture, art, and music. The opposite of symmetry is asymmetry, w ...
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Organic Letters
''Organic Letters'' is a biweekly peer-reviewed scientific journal covering research in organic chemistry. It was established in 1999 and is published by the American Chemical Society. In 2014, the journal moved to a hybrid open access publishing model. The founding editor-in-chief was Amos Smith. The current editor-in-chief is Marisa C. Kozlowski. The journal is abstracted and indexed in: the Science Citation Index Expanded, Scopus, Academic Search Premier, BIOSIS Previews, Chemical Abstracts Service, EMBASE, and MEDLINE MEDLINE (Medical Literature Analysis and Retrieval System Online, or MEDLARS Online) is a bibliographic database of life sciences and biomedical information. It includes bibliographic information for articles from academic journals covering medic .... References External links * American Chemical Society academic journals Biweekly journals Organic chemistry journals Academic journals established in 1999 English-language journals {{chem-journal-s ...
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Trimethylsilylacetylene
Trimethylsilylacetylene is the organosilicon compound with the formula . A colorless liquid, "tms acetylene", as it is also called, is used as a source of anion in organic synthesis. Use Trimethylsilylacetylene is used in Sonogashira couplings as the equivalent of acetylene. Using this protected alkyne, as opposed to acetylene itself, prevents further coupling reactions. The trimethylsilyl group can then be cleaved off with TBAF or DBU to form phenylacetylene derivatives. Trimethylsilylacetylene is also used to synthesize diphenylacetylene derivatives in a one-pot Sonogashira coupling, in which the phenylacetylene derivative reacts with a second aryl halide after in-situ deprotection. A less expensive alternative reagent is 2-methylbut-3-yn-2-ol, which after alkynylation is deprotected with base. Trimethylsilylacetylene is commercially available. It may also be prepared in a manner similar to other silyl compounds: deprotonation of acetylene with a Grignard reagent, fo ...
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Acetylene
Acetylene (Chemical nomenclature, systematic name: ethyne) is a chemical compound with the formula and structure . It is a hydrocarbon and the simplest alkyne. This colorless gas is widely used as a fuel and a chemical building block. It is unstable in its pure form and thus is usually handled as a solution. Pure acetylene is odorless, but commercial grades usually have a marked odor due to impurities such as divinyl sulfide and phosphine.Compressed Gas Association (1995Material Safety and Data Sheet – Acetylene As an alkyne, acetylene is Saturated and unsaturated compounds, unsaturated because its two carbon atoms are Chemical bond, bonded together in a triple bond. The carbon–carbon triple bond places all four atoms in the same straight line, with CCH bond angles of 180°. The triple bond in acetylene results in a high energy content that is released when acetylene is burned. Discovery Acetylene was discovered in 1836 by Edmund Davy, who identified it as a "new carburet ...
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Sonogashira Coupling
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. :* : aryl or vinyl :* R2: arbitrary :* X: I, Br, Cl or OTf The Sonogashira cross-coupling reaction has been employed in a wide variety of areas, due to its usefulness in the formation of carbon–carbon bonds. The reaction can be carried out under mild conditions, such as at room temperature, in aqueous media, and with a mild base, which has allowed for the use of the Sonogashira cross-coupling reaction in the synthesis of complex molecules. Its applications include pharmaceuticals, natural products, organic materials, and nanomaterials. Specific examples include its use in the synthesis of tazarotene, which is a treatment for psoriasis and acne, and in the preparation of SIB-1508Y, also known as Altinicline, a nicotinic rece ...
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