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Bromoiodomethane
Bromoiodomethane is a halomethane with the formula BrCH2I. It is a colorless liquid, although older samples appear yellow. The compound has been investigated as a reagent for cyclopropanation by the Simmons-Smith reaction, but diiodomethane and chloroiodomethane Chloroiodomethane is the halomethane with the formula is . It is a colorless liquid of use in organic synthesis. Together with other iodomethanes, chloroiodomethane is produced by some microorganisms. Applications Chloroiodomethane is used in c ... are preferred. It also occurs naturally as the result of microbial action. Its critical point is at 367.85 °C and 6.3 MPa and refractive index is 1.6382 (20 °C, D). Additional reading * * * * References External linksUV Spectra data Halomethanes Organobromides Organoiodides {{Organohalide-stub ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Bromomethane
Bromomethane, commonly known as methyl bromide, is an organobromine compound with formula C H3 Br. This colorless, odorless, nonflammable gas is produced both industrially and biologically. It has a tetrahedral shape and it is a recognized ozone-depleting chemical. It was used extensively as a pesticide until being phased out by most countries in the early 2000s. Occurrence and manufacture Bromomethane originates from both natural and human sources. In the ocean, marine organisms are estimated to produce 56,000 tonnes annually. It is also produced in small quantities by certain terrestrial plants, such as members of the family Brassicaceae. It is manufactured for agricultural and industrial use by treating methanol with bromine in the presence of sulfur or hydrogen sulfide: :6 CH3OH + 3 Br2 + S → 6 CH3Br + 2 H2O + H2SO4 Uses In 1999, an estimated 71,500 tonnes of synthetic methyl bromide were used annually worldwide. 97% of this estimate was used for fumigation purposes, wh ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Bromoethane
Bromoethane, also known as ethyl bromide, is a chemical compound of the haloalkanes group. It is abbreviated by chemists as EtBr (which is also used as an abbreviation for ethidium bromide). This volatile compound has an ether-like odor. Preparation The preparation of EtBr stands as a model for the synthesis of bromoalkanes in general. It is usually prepared by the addition of hydrogen bromide to ethene: :H2C=CH2 + HBr → H3C-CH2Br Bromoethane is inexpensive and would rarely be prepared in the laboratory. A laboratory synthesis includes reacting ethanol with a mixture of hydrobromic and sulfuric acids. An alternate route involves refluxing ethanol with phosphorus and bromine; phosphorus tribromide is generated ''in situ''. Uses In organic synthesis, EtBr is the synthetic equivalent of the ethyl carbocation (Et+) synthon. In reality, such a cation is not actually formed. For example, carboxylates salts are converted to ethyl esters, carbanions to ethylated derivatives, thiour ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Halomethane
Halomethane compounds are derivatives of methane () with one or more of the hydrogen atoms replaced with halogen atoms ( F, Cl, Br, or I). Halomethanes are both naturally occurring, especially in marine environments, and human-made, most notably as refrigerants, solvents, propellants, and fumigants. Many, including the chlorofluorocarbons, have attracted wide attention because they become active when exposed to ultraviolet light found at high altitudes and destroy the Earth's protective ozone layer. Structure and properties Like methane itself, halomethanes are tetrahedral molecules. The halogen atoms differ greatly in size and charge from hydrogen and from each other. Consequently, most halomethanes deviate from the perfect tetrahedral symmetry of methane.Günter Siegemund, Werner Schwertfeger, Andrew Feiring, Bruce Smart, Fred Behr, Herward Vogel, Blaine McKusick “Fluorine Compounds, Organic” Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2002. The ph ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Cyclopropanation
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 (ciprofloxacin, sparfloxacin, etc.). 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. 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, which is typically formed by a reaction between diiodomethane and a z ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Diiodomethane
Diiodomethane or methylene iodide, commonly abbreviated "MI", is an organoiodine compound. Diiodomethane is a colorless liquid; however, it decomposes upon exposure to light liberating iodine, which colours samples brownish. It is slightly soluble in water, but soluble in organic solvents. It has a relatively high refractive index of 1.741, and a surface tension of 0.0508 N·m−1.Website of Krüss'' (8.10.2009) Uses Because of its high density, diiodomethane is used in the determination of the density of mineral and other solid samples. It can also be used as an optical contact liquid, in conjunction with the gemmological refractometer, for determining the refractive index of certain gemstones. Diiodomethane is a reagent for installing the CH2 group. In the Simmons–Smith reaction, it is a source of methylene. In fact the Simmons–Smith reaction does not produce free carbene but proceeds via Zn-CH2I intermediates. Diiodomethane is also a source of the equivalent of CH22+. ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Chloroiodomethane
Chloroiodomethane is the halomethane with the formula is . It is a colorless liquid of use in organic synthesis. Together with other iodomethanes, chloroiodomethane is produced by some microorganisms. Applications Chloroiodomethane is used in cyclopropanation (''Simmon-Smith reaction''), where it often replaces diiodomethane because of higher yields and selectivity. It is also used in Mannich reaction, aminomethylation, epoxidation, ring opening and addition to terminal alkenes. It is a precursor to chloromethylenating agent Ph3P=CHCl. It reacts with organolithium compounds to give chloromethyllithium (ClCH2Li). Crystallography It crystallizes orthorhombic crystal system with space group ''Pnma'' with lattice constants A lattice constant or lattice parameter is one of the physical dimensions and angles that determine the geometry of the unit cells in a crystal lattice, and is proportional to the distance between atoms in the crystal. A simple cubic crystal has ...: ''a'' = ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Halomethanes
Halomethane compounds are derivatives of methane () with one or more of the hydrogen atoms replaced with halogen atoms ( F, Cl, Br, or I). Halomethanes are both naturally occurring, especially in marine environments, and human-made, most notably as refrigerants, solvents, propellants, and fumigants. Many, including the chlorofluorocarbons, have attracted wide attention because they become active when exposed to ultraviolet light found at high altitudes and destroy the Earth's protective ozone layer. Structure and properties Like methane itself, halomethanes are tetrahedral molecules. The halogen atoms differ greatly in size and charge from hydrogen and from each other. Consequently, most halomethanes deviate from the perfect tetrahedral symmetry of methane.Günter Siegemund, Werner Schwertfeger, Andrew Feiring, Bruce Smart, Fred Behr, Herward Vogel, Blaine McKusick “Fluorine Compounds, Organic” Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2002. The ph ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Organobromides
Organobromine compounds, also called organobromides, are organic compounds that contain carbon bonded to bromine. The most pervasive is the naturally produced bromomethane. One prominent application of synthetic organobromine compounds is the use of polybrominated diphenyl ethers as fire-retardants, and in fact fire-retardant manufacture is currently the major industrial use of the element bromine. A variety of minor organobromine compounds are found in nature, but none are biosynthesized or required by mammals. Organobromine compounds have fallen under increased scrutiny for their environmental impact. General properties Most organobromine compounds, like most organohalide compounds, are relatively nonpolar. Bromine is more electronegative than carbon (2.9 vs 2.5). Consequently, the carbon in a carbon–bromine bond is electrophilic, i.e. alkyl bromides are alkylating agents. Carbon–halogen bond strengths, or bond dissociation energies are of 115, 83.7, 72.1, and 57.6 kc ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
