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Diiodomethane
Diiodomethane or methylene iodide, commonly abbreviated "MI", is an organoiodine compound. Diiodomethane is a very dense 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 very 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 . ...
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Dibromomethane
Dibromomethane or methylene bromide, or methylene dibromide is a halomethane with the formula CH2Br2. It is slightly soluble in water but very soluble in organic solvents. It is a colorless liquid. Physical properties At ambient temperature, dibromomethane solidifies around 0.61 GPa. The crystal structure strongly suggests both interhalogen and hydrogen-halogen interactions. Preparation Dibromomethane is prepared commercially from dichloromethane via bromochloromethane: :6 CH2Cl2 + 3 Br2 + 2 Al → 6 CH2BrCl + 2 AlCl3 :CH2Cl2 + HBr → CH2BrCl + HCl The latter route requires aluminium trichloride as a catalyst. The bromochloromethane product from either reaction can further react in a similar manner: :6 CH2BrCl + 3 Br2 + 2 Al → 6 CH2Br2 + 2 AlCl3 :CH2BrCl + HBr → CH2Br2 + HCl In the laboratory, it is prepared from bromoform using sodium arsenite and sodium hydroxide: :CHBr3 + Na3AsO3 + NaOH → CH2Br2 + Na3AsO4 + NaBr Another way is to prepare i ...
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Simmons–Smith Reaction
The Simmons–Smith reaction is an organic cheletropic reaction involving an organozinc carbenoid that reacts with an alkene (or alkyne) to form a cyclopropane. It is named after Howard Ensign Simmons, Jr. and Ronald D. Smith. It uses a methylene free radical intermediate that is delivered to both carbons of the alkene simultaneously, therefore the configuration of the double bond is preserved in the product and the reaction is stereospecific. Mechanism Examples Thus, cyclohexene, diiodomethane, and a zinc-copper couple (as iodomethylzinc iodide, ) yield norcarane (bicyclo .1.0eptane). : The Simmons–Smith reaction is generally preferred over other methods of cyclopropanation, however it can be expensive due to the high cost of diiodomethane. Modifications involving cheaper alternatives have been developed, such as dibromomethane or diazomethane and zinc iodide. The reactivity of the system can also be increased by using the Furukawa modification, exchanging ...
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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 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 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 diiodomet ...
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Iodoform
Iodoform (also known as triiodomethane) is the organoiodine compound with the chemical formula . It is a pale yellow, crystalline, volatile substance, with a penetrating and distinctive odor (in older chemistry texts, the smell is sometimes referred to as that of hospitals, where the compound is still commonly used) and, analogous to chloroform, sweetish taste. It is occasionally used as a disinfectant. Naming The name iodoform originates with the "formyle radical," an archaic term for the HC moiety, and is retained for historical consistency. A full, modern name is triiodomethane. Another possible name is "carbon hydride triiodide". The "hydride" in the latter is sometimes omitted, though the IUPAC recommends against doing so, as "carbon triiodide" could also mean (hexaiodoethane, a highly unstable compound). Structure The molecule adopts a tetrahedral molecular geometry, tetrahedral geometry with C3v symmetry group, symmetry. Synthesis and reactions The synthesis of iodofo ...
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Methane
Methane ( , ) is a chemical compound with the chemical formula (one carbon atom bonded to four hydrogen atoms). It is a group-14 hydride, the simplest alkane, and the main constituent of natural gas. The abundance of methane on Earth makes it an economically attractive fuel, although capturing and storing it is difficult because it is a gas at standard temperature and pressure. In the Earth's atmosphere methane is transparent to visible light but absorbs infrared radiation, acting as a greenhouse gas. Methane is an Organic chemistry, organic Organic compound, compound, and among the simplest of organic compounds. Methane is also a hydrocarbon. Naturally occurring methane is found both below ground and under the seafloor and is formed by both geological and biological processes. The largest reservoir of methane is under the seafloor in the form of methane clathrates. When methane reaches the surface and the Atmosphere of Earth, atmosphere, it is known as atmospheric methane. ...
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Iodoalkanes
Organoiodine chemistry is the study of the synthesis and properties of organoiodine compounds, or organoiodides, organic compounds that contain one or more carbon–iodine Chemical bond, 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 iodized salt, iodization of salt. Structure, bonding, general properties Almost all organoiodine compounds feature iodide connected to one carbon center. These are usually classified as derivatives of I−. Some organoiodine compounds feature iodine in higher oxidation states. The C–I bond is the weakest of the carbon–halogen bonds. These bond strengths correlate with the electronegativity of the halogen, decreasing in the order F > Cl > Br > I. This periodic table, periodic order also follows the atomic radius of halogens and the length of the carbon-halogen bond. For example, in ...
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Alkylating Agent
Alkylation is a chemical reaction that entails transfer of an alkyl group. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion, or a carbene (or their equivalents). Alkylating agents are reagents for effecting alkylation. Alkyl groups can also be removed in a process known as dealkylation. Alkylating agents are often classified according to their nucleophilic or electrophilic character. In oil refining contexts, alkylation refers to a particular alkylation of isobutane with olefins. For upgrading of petroleum, alkylation produces a premium blending stock for gasoline. In medicine, alkylation of DNA is used in chemotherapy to damage the DNA of cancer cells. Alkylation is accomplished with the class of drugs called alkylating antineoplastic agents. Nucleophilic alkylating agents Nucleophilic alkylating agents deliver the equivalent of an alkyl anion ( carbanion). The formal "alkyl anion" attacks an electrophile, forming a new covalent bond b ...
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Sodium Arsenite
Sodium arsenite usually refers to the inorganic compound with the formula NaAsO2. Also called sodium ''meta''-arsenite, it is an inorganic polymer consisting of the infinite chains [AsO2] associated with sodium cations, Na+. The polymer backbone has the connectivity -O-As(O−)-.backbone. Sodium ''ortho''-arsenite is Na3AsO3.Greenwood, N. N.; & Earnshaw, A. (1997). Chemistry of the Elements (2nd Edn.), Oxford:Butterworth-Heinemann. . Both compounds are colourless solids. A mixture of sodium ''meta''-arsenite and sodium ''ortho''-arsenite is produced by treating arsenic trioxide with sodium carbonate or sodium hydroxide. Sodium arsenite is amorphous, typically being obtained as a powder or as a glassy mass. Health effects Sodium arsenite can be inhaled or absorbed through the skin. Along with its known carcinogenic and teratogenic effects, contact with the substance can yield symptoms such as skin irritation, burns, itching, thickened skin, rash, loss of pigment, poor appetit ...
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Phosphorus
Phosphorus is a chemical element; it has Chemical symbol, symbol P and atomic number 15. All elemental forms of phosphorus are highly Reactivity (chemistry), reactive and are therefore never found in nature. They can nevertheless be prepared artificially, the two most common allotropes being white phosphorus and red phosphorus. With as its only stable isotope, phosphorus has an occurrence in Earth's crust of about 0.1%, generally as phosphate rock. A member of the pnictogen family, phosphorus readily forms a wide variety of organic compound, organic and inorganic compound, inorganic compounds, with as its main oxidation states +5, +3 and −3. The isolation of white phosphorus in 1669 by Hennig Brand marked the scientific community's first discovery since Antiquity of an element. The name phosphorus is a reference to the Phosphorus (morning star), god of the Morning star in Greek mythology, inspired by the faint glow of white phosphorus when exposed to oxygen. This property is ...
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Finkelstein Reaction
The Finkelstein reaction, named after the German chemist Hans Finkelstein, is a type of SN2 reaction (substitution nucleophilic bimolecular reaction) that involves the exchange of one halogen atom for another. It is an equilibrium reaction, but the reaction can be driven to completion by exploiting the differential solubility of various halide salts, or by using a large excess of the desired halide. Method The classic Finkelstein reaction entails the conversion of an alkyl chloride or an alkyl bromide to an alkyl iodide by treatment with a solution of sodium iodide in acetone. Sodium iodide is soluble in acetone while sodium chloride and sodium bromide are not; therefore, the reaction is driven toward products by mass action due to the precipitation of the poorly soluble NaCl or NaBr. An example involves the conversion of the ethyl ester of 5-bromovaleric acid to the iodide: :EtO2C(CH2)4Br + NaI → EtO2C(CH2)4I + NaBr Potassium fluoride is used for the conversio ...
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Acetone
Acetone (2-propanone or dimethyl ketone) is an organic compound with the chemical formula, formula . It is the simplest and smallest ketone (). It is a colorless, highly Volatile organic compound, volatile, and flammable liquid with a characteristic pungent odor. Acetone is miscibility, miscible with properties of water, water and serves as an important organic solvent in industry, home, and laboratory. About 6.7 million tonnes were produced worldwide in 2010, mainly for use as a solvent and for production of methyl methacrylate and bisphenol A, which are precursors to widely used plastics.Acetone
World Petrochemicals report, January 2010
Stylianos Sifniades, Alan B. Levy, "Acetone" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005. It is a common building block in organic chemistry. ...
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