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Phenyl(bromodichloromethyl)mercury
Phenyl(trichloromethyl)mercury is an organomercury compound with the formula C6H5HgCCl3. It is a white solid that is soluble in organic solvents. The compound is used as a source of dichlorocarbene, e.g. in cyclopropanation reactions, because the products are particularly easy to extract from the reaction mixture. Strong nucleophiles may catalyze the reaction by displacing CCl from mercury, although the free ion is not believed to form in the process. Unusually, the pure organomercury compound reacts with electron-poor alkenes, converting tetrachloroethylene to hexachlorocyclopropane: :C6H5HgCCl3 → C6H5HgCl + CCl2 :CCl2 + Cl2C=CCl2 → C3Cl6 The compound is prepared by treating with sources of dichlorocarbene. These include the base/haloform reaction and thermolysis of sodium trichloroacetate: :NaO2CCCl3 + C6H5HgCl → C6H5HgCCl3 + NaCl + CO2 Related compounds Closely related compounds include phenyl(bromodichloromethyl)mercury (CAS registry number 329 ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Organomercury Compound
Organomercury chemistry refers to the study of organometallic compounds that contain mercury. Many organomercury compounds are highly toxic, but some are used in medicine, e.g., merbromin ("Mercurochrome") and the vaccine preservative thiomersal. Structure and bonding Most organomercury compounds feature diamagnetic Hg(II) and adopt a linear C-Hg-X structure. Indeed, no organic derivatives of Hg are known, as Hg requires electronegative subtituents for condensed-phase stability. Hg(II) derivatives are neither Lewis basic or Lewis acidic. They are stable to oxygen and water, indicating the low polarity of the Hg-C bond. Mercury forms a compound with two cyclopentadiene ligands, but the resulting complex may not be a metallocene. When made in the 1950s, it was too sensitive for structural determination. Toxicity The toxicity of organomercury compounds presents both dangers and benefits. Dimethylmercury in particular is notoriously toxic, but found use as an antifungal ag ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Phenyl
In organic chemistry, the phenyl group, or phenyl ring, is a cyclic group of atoms with the formula , and is often represented by the symbol Ph (archaically φ) or Ø. The phenyl group is closely related to benzene and can be viewed as a benzene ring, minus a hydrogen atom, which may be replaced by some other element or compound to serve as a functional group. A phenyl group has six carbon atoms bonded together in a hexagonal planar ring, five of which are bonded to individual hydrogen atoms, with the remaining carbon bonded to a substituent. Phenyl groups are commonplace in organic chemistry. Although often depicted with alternating double and single bonds, the phenyl group is chemically aromatic and has equal bond lengths between carbon atoms in the ring. Nomenclature Usually, a "phenyl group" is synonymous with and is represented by the symbol Ph (archaically, Φ), or Ø. Benzene is sometimes denoted as PhH. Phenyl groups are generally attached to other atoms or groups. Fo ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Organic Solvent
A solvent (from the Latin '' solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a solution. A solvent is usually a liquid but can also be a solid, a gas, or a supercritical fluid. Water is a solvent for polar molecules, and the most common solvent used by living things; all the ions and proteins in a cell are dissolved in water within the cell. Major uses of solvents are in paints, paint removers, inks, and dry cleaning. Specific uses for organic solvents are in dry cleaning (e.g. tetrachloroethylene); as paint thinners (toluene, turpentine); as nail polish removers and solvents of glue (acetone, methyl acetate, ethyl acetate); in spot removers (hexane, petrol ether); in detergents ( citrus terpenes); and in perfumes (ethanol). Solvents find various applications in chemical, pharmaceutical, oil, and gas industries, including in chemical syntheses and purification processes Some petrochemical solvents are highly toxic and emit volatile ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Dichlorocarbene
Dichlorocarbene is the reactive intermediate with chemical formula CCl2. Although this chemical species has not been isolated, it is a common intermediate in organic chemistry, being generated from chloroform. This bent diamagnetic molecule rapidly inserts into other bonds. Preparation Dichlorocarbene is most commonly generated by reaction of chloroform and a base such as potassium tert-butoxide, potassium ''tert''-butoxide or aqueous sodium hydroxide. A phase transfer catalyst, for instance quaternary ammonium cation, benzyltriethylammonium bromide, facilitates the migration of the hydroxide in the organic phase. :HCCl3 + NaOH → CCl2 + NaCl + H2O Other reagents and routes Another precursor to dichlorocarbene is ethyl trichloroacetate. Upon treatment with sodium methoxide it releases CCl2. Phenyl(trichloromethyl)mercury decomposes thermally to release CCl2. :PhHgCCl3 → CCl2 + PhHgCl Dichlorodiazirine, which is stable in the dark, chemical decomposition, decomposes into dic ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Cyclopropanation
In organic chemistry, cyclopropanation refers to any chemical process which generates cyclopropane () Ring (chemistry), rings. It is an important process in modern chemistry as many useful compounds bear this motif; for example pyrethroid insecticides and a number of quinolone antibiotics (ciprofloxacin, sparfloxacin, etc.). However, the high ring strain present in cyclopropanes makes them challenging to produce and generally requires the use of highly Reactivity (chemistry), reactive species, such as carbenes, ylids and carbanions. Many of the reactions proceed in a cheletropic reaction, cheletropic manner. Approaches From alkenes using carbenoid reagents Several methods exist for converting alkenes to cyclopropane rings using carbene type reagents. As carbenes themselves are highly reactive it is common for them to be used in a stabilised form, referred to as a carbenoid. Simmons–Smith reaction In the Simmons–Smith reaction the reactive carbenoid is iodomethylzinc iodide, ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Haloform
In chemistry, trihalomethanes (THMs) are chemical compounds in which three of the four hydrogen atoms of methane () are replaced by halogen atoms. Trihalomethanes with all the same halogen atoms are called haloforms. Many trihalomethanes find uses in industry as solvents or refrigerants. Some THMs are also environmental pollutants, and a few are considered carcinogenic. Table of common trihalomethanes Industrial uses Only chloroform has significant applications of the haloforms. In the predominant application, chloroform is required for the production of tetrafluoroethylene (TFE), precursor to teflon. Chloroform is fluorinated by reaction with hydrogen fluoride to produce chlorodifluoromethane (R-22). Pyrolysis of chlorodifluoromethane (at 550-750 °C) yields TFE, with difluorocarbene as an intermediate. :CHCl3 + 2 HF -> CHClF2 + 2 HCl :2 CHClF2 -> C2F4 + 2 HCl Refrigerants and solvents Trihalomethanes released to the environment break down faster than chlorofluorocarbons ( ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Sodium Trichloroacetate
Sodium trichloroacetate is a chemical compound with a formula of CCl3CO2Na. It is used to increase sensitivity and precision during transcript mapping. It was previously used as an herbicide starting in the 1950s but regulators removed it from the market in the late 1980s and early 1990s. Preparation Sodium trichloroacetate is made by reaction trichloroacetic acid with sodium hydroxide: : Reactions Basicity Sodium trichloroacetate is a weaker base than sodium acetate because of the electron-withdrawing nature of the trichloromethyl group. Sodium trifluoroacetate is likewise a weaker base. However, it can easily be protonated in the presence of suitably strong acids: : Trichloromethyl-anion precursor This reagent is useful for introducing the trichloromethyl group into other molecules. Decarboxylation produces the trichloromethyl anion, which is a sufficiently strong nucleophile to attack various carbonyl functional groups, such as aldehydes, carboxylic acid anhydride ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Organic Syntheses
''Organic Syntheses'' is a peer-reviewed scientific journal that was established in 1921. It publishes detailed and checked procedures for the synthesis of organic compounds. A unique feature of the review process is that all of the data and experiments reported in an article must be successfully repeated in the laboratory of a member of the editorial board as a check for reproducibility prior to publication. The journal is published by Organic Syntheses, Inc., a non-profit corporation. An annual print version is published by John Wiley & Sons on behalf of Organic Syntheses, Inc. History Prior to World War I, work on synthetic organic chemistry in the United States had been quite limited, and most of the reagents used in laboratories had to be imported from Europe. When export stoppages and trade embargoes cut off this source, Clarence Derick, a professor of chemistry at University of Illinois at Urbana-Champaign, began an effort to synthesize these needed chemicals in industri ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
X-ray Crystallography
X-ray crystallography is the experimental science of determining the atomic and molecular structure of a crystal, in which the crystalline structure causes a beam of incident X-rays to Diffraction, diffract in specific directions. By measuring the angles and intensities of the X-ray diffraction, a crystallography, crystallographer can produce a three-dimensional picture of the density of electrons within the crystal and the positions of the atoms, as well as their chemical bonds, crystallographic disorder, and other information. X-ray crystallography has been fundamental in the development of many scientific fields. In its first decades of use, this method determined the size of atoms, the lengths and types of chemical bonds, and the atomic-scale differences between various materials, especially minerals and alloys. The method has also revealed the structure and function of many biological molecules, including vitamins, drugs, proteins and nucleic acids such as DNA. X-ray crystall ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Organomercury Compounds
Organomercury chemistry refers to the study of organometallic compounds that contain mercury. Many organomercury compounds are highly toxic, but some are used in medicine, e.g., merbromin ("Mercurochrome") and the vaccine preservative thiomersal. Structure and bonding Most organomercury compounds feature diamagnetic Hg(II) and adopt a linear C-Hg-X structure. Indeed, no organic derivatives of Hg are known, as Hg requires electronegative subtituents for condensed-phase stability. Hg(II) derivatives are neither Lewis basic or Lewis acidic. They are stable to oxygen and water, indicating the low polarity of the Hg-C bond. Mercury forms a compound with two cyclopentadiene ligands, but the resulting complex may not be a metallocene. When made in the 1950s, it was too sensitive for structural determination. Toxicity The toxicity of organomercury compounds presents both dangers and benefits. Dimethylmercury in particular is notoriously toxic, but found use as an antifungal ag ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Phenyl Compounds
In organic chemistry, the phenyl group, or phenyl ring, is a cyclic group of atoms with the formula , and is often represented by the symbol Ph (archaically φ) or Ø. The phenyl group is closely related to benzene and can be viewed as a benzene ring, minus a hydrogen atom, which may be replaced by some other element or compound to serve as a functional group. A phenyl group has six carbon atoms bonded together in a hexagonal planar ring, five of which are bonded to individual hydrogen atoms, with the remaining carbon bonded to a substituent. Phenyl groups are commonplace in organic chemistry. Although often depicted with alternating double and single bonds, the phenyl group is chemically aromatic and has equal bond lengths between carbon atoms in the ring. Nomenclature Usually, a "phenyl group" is synonymous with and is represented by the symbol Ph (archaically, Φ), or Ø. Benzene is sometimes denoted as PhH. Phenyl groups are generally attached to other atoms or groups. Fo ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
