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Diphenyl Disulfide
Diphenyl disulfide is the chemical compound with the formula (C6H5S)2. This colorless crystalline material is often abbreviated Ph2S2. It is one of the more commonly encountered organic disulfides in organic synthesis. Minor contamination by thiophenol is responsible for the disagreeable odour associated with this compound. Preparation and structure Diphenyl disulfide is usually prepared by the oxidation of thiophenol: : 2 PhSH + I2 → Ph2S2 + 2 HI Hydrogen peroxide can also be used as the oxidant. Ph2S2 is rarely prepared in the laboratory because it is inexpensive, and the precursor has a disagreeable odour. Like most organic disulfides, the C–S–S–C core of Ph2S2 is non-planar with a dihedral angle approaching 85°. Reactions Ph2S2 is mainly used in organic synthesis as a source of the PhS substituent. A typical reaction entails the formation of PhS-substituted carbonyl compounds via the enolate: :RC(O)CHLiR' + Ph2S2 → RC(O)CH(SPh)R' + LiSPh Reduction Ph2S2 underg ...
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Diethyl Ether
Diethyl ether, or simply ether, is an organic compound in the ether class with the formula , sometimes abbreviated as (see Pseudoelement symbols). It is a colourless, highly volatile, sweet-smelling ("ethereal odour"), extremely flammable liquid. It is commonly used as a solvent in laboratories and as a starting fluid for some engines. It was formerly used as a general anesthetic, until non-flammable drugs were developed, such as halothane. It has been used as a recreational drug to cause intoxication. Production Most diethyl ether is produced as a byproduct of the vapor-phase hydration of ethylene to make ethanol. This process uses solid-supported phosphoric acid catalysts and can be adjusted to make more ether if the need arises. Vapor-phase dehydration of ethanol over some alumina catalysts can give diethyl ether yields of up to 95%. Diethyl ether can be prepared both in laboratories and on an industrial scale by the acid ether synthesis. Ethanol is mixed with a ...
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Lithium Triethylborohydride
Lithium triethylborohydride is the organoboron compound with the formula Li Et3 BH. Commonly referred to as LiTEBH or Superhydride, it is a powerful reducing agent used in organometallic and organic chemistry. It is a colorless or white liquid but is typically marketed and used as a THF solution. The related reducing agent sodium triethylborohydride is commercially available as toluene solutions. LiBHEt3 is a stronger reducing agent than lithium borohydride and lithium aluminium hydride. Preparation LiBHEt3 is prepared by the reaction of lithium hydride (LiH) and triethylborane (Et3B) in tetrahydrofuran (THF): :LiH + Et3B → LiEt3BH Its THF solutions are stable indefinitely in the absence of moisture and air. Reactions Alkyl halides are reduced to the alkanes by LiBHEt3. LiBHEt3 reduces a wide range of functional groups, but so do many other hydride reagents. Instead, LiBHEt3 is reserved for difficult substrates, such as sterically hindered carbonyls, as illustrated by redu ...
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Methanol
Methanol (also called methyl alcohol and wood spirit, amongst other names) is an organic chemical and the simplest aliphatic alcohol, with the formula C H3 O H (a methyl group linked to a hydroxyl group, often abbreviated as MeOH). It is a light, volatile, colourless, flammable liquid with a distinctive alcoholic odour similar to that of ethanol (potable alcohol). A polar solvent, methanol acquired the name wood alcohol because it was once produced chiefly by the destructive distillation of wood. Today, methanol is mainly produced industrially by hydrogenation of carbon monoxide. Methanol consists of a methyl group linked to a polar hydroxyl group. With more than 20 million tons produced annually, it is used as a precursor to other commodity chemicals, including formaldehyde, acetic acid, methyl tert-butyl ether, methyl benzoate, anisole, peroxyacids, as well as a host of more specialised chemicals. Occurrence Small amounts of methanol are present in normal, healthy ...
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Lead(IV) Acetate
Lead(IV) acetate or lead tetraacetate is an organometallic compound with chemical formula . It is a colorless solid that is soluble in nonpolar, organic solvents, indicating that it is not a salt. It is degraded by moisture and is typically stored with additional acetic acid. The compound is used in organic synthesis. Structure In the solid state the lead(IV) centers are coordinated by four acetate ions, which are bidentate, each coordinating via two oxygen atoms. The lead atom is 8 coordinate and the O atoms form a flattened trigonal dodecahedron. Preparation It is typically prepared by treating of red lead with acetic acid and acetic anhydride (), which absorbs water. The net reaction is shown: :Pb3O4 + 4 Ac2O -> Pb(OAc)4 + 2 Pb(OAc)2 The remaining lead(II) acetate can be partially oxidized to the tetraacetate: :2 Pb(OAc)2 + Cl2 -> Pb(OAc)4 + PbCl2 Reagent in organic chemistry Lead tetraacetate is a strong oxidizing agent, a source of acetyloxy groups and a general reagen ...
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Alkene
In organic chemistry, an alkene is a hydrocarbon containing a carbon–carbon double bond. Alkene is often used as synonym of olefin, that is, any hydrocarbon containing one or more double bonds.H. Stephen Stoker (2015): General, Organic, and Biological Chemistry'. 1232 pages. Two general types of monoalkenes are distinguished: terminal and internal. Also called α-olefins, terminal alkenes are more useful. However, the International Union of Pure and Applied Chemistry (IUPAC) recommends using the name "alkene" only for acyclic hydrocarbons with just one double bond; alkadiene, alkatriene, etc., or polyene for acyclic hydrocarbons with two or more double bonds; cycloalkene, cycloalkadiene, etc. for cyclic ones; and "olefin" for the general class – cyclic or acyclic, with one or more double bonds. Acyclic alkenes, with only one double bond and no other functional groups (also known as mono-enes) form a homologous series of hydrocarbons with the general formula with ...
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Cis–trans Isomerism
''Cis''–''trans'' isomerism, also known as geometric isomerism or configurational isomerism, is a term used in chemistry that concerns the spatial arrangement of atoms within molecules. The prefixes "''cis''" and "''trans''" are from Latin: "this side of" and "the other side of", respectively. In the context of chemistry, ''cis'' indicates that the functional groups (substituents) are on the same side of some plane, while ''trans'' conveys that they are on opposing (transverse) sides. ''Cis''–''trans'' isomers are stereoisomers, that is, pairs of molecules which have the same formula but whose functional groups are in different orientations in three-dimensional space. ''Cis-trans'' notation does not always correspond to ''E''–''Z'' isomerism, which is an ''absolute'' stereochemical description. In general, ''cis''–''trans'' stereoisomers contain double bonds that do not rotate, or they may contain ring structures, where the rotation of bonds is restricted or prevented ...
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Phenylsulfur Pentafluoride
Pentafluorosulfanylbenzene, or phenylsulfur pentafluoride, is an organosulfur compound with the formula C6H5SF5. It is colorless liquid with high chemical stability. Reactivity Pentafluorosulfanylbenzene possesses high chemical stability under a wide range of conditions including oxidizing, reducing, strongly acidic and strongly basic environments. For example, it does not react with a refluxing solution of sodium hydroxide in aqueous ethanol, but it can react with concentrated sulfuric acid at elevated temperatures. The pentafluorosulfanyl group is a strong electron withdrawing group, and leads to electrophilic aromatic substitution reactions at the meta position. Synthesis Pentafluorosulfanylbenzene was originally synthesized by fluorination of diphenyl disulfide by AgF2, a method that suffers from low yield. The best known method of synthesis is the fluorination of diphenyl disulfide with xenon difluoride Xenon difluoride is a powerful fluorinating agent with the ...
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Xenon Difluoride
Xenon difluoride is a powerful fluorinating agent with the chemical formula , and one of the most stable xenon compounds. Like most covalent inorganic fluorides it is moisture-sensitive. It decomposes on contact with water vapor, but is otherwise stable in storage. Xenon difluoride is a dense, colourless crystalline solid. It has a nauseating odour and low vapor pressure. Structure Xenon difluoride is a linear molecule with an Xe–F bond length of in the vapor stage, and 200 pm in the solid phase. The packing arrangement in solid shows that the fluorine atoms of neighbouring molecules avoid the equatorial region of each molecule. This agrees with the prediction of VSEPR theory, which predicts that there are 3 pairs of non-bonding electrons around the equatorial region of the xenon atom. At high pressures, novel, non-molecular forms of xenon difluoride can be obtained. Under a pressure of ~50 GPa, transforms into a semiconductor consisting of units linked in ...
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In Situ
''In situ'' (; often not italicized in English) is a Latin phrase that translates literally to "on site" or "in position." It can mean "locally", "on site", "on the premises", or "in place" to describe where an event takes place and is used in many different contexts. For example, in fields such as physics, geology, chemistry, or biology, ''in situ'' may describe the way a measurement is taken, that is, in the same place the phenomenon is occurring without isolating it from other systems or altering the original conditions of the test. The opposite of ''in situ'' is ''ex situ''. Aerospace In the aerospace industry, equipment on-board aircraft must be tested ''in situ'', or in place, to confirm everything functions properly as a system. Individually, each piece may work but interference from nearby equipment may create unanticipated problems. Special test equipment is available for this ''in situ'' testing. It can also refer to repairs made to the aircraft structure or flight con ...
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Zincke Disulfide Cleavage
In biochemistry, a disulfide (or disulphide in British English) refers to a functional group with the structure . The linkage is also called an SS-bond or sometimes a disulfide bridge and is usually derived by the coupling of two thiol groups. In biology, disulfide bridges formed between thiol groups in two cysteine residues are an important component of the secondary and tertiary structure of proteins. ''Persulfide'' usually refers to compounds. In inorganic chemistry disulfide usually refers to the corresponding anion (−S−S−). Organic disulfides Symmetrical disulfides are compounds of the formula . Most disulfides encountered in organo sulfur chemistry are symmetrical disulfides. Unsymmetrical disulfides (also called heterodisulfides) are compounds of the formula . They are less common in organic chemistry, but most disulfides in nature are unsymmetrical. Properties The disulfide bonds are strong, with a typical bond dissociation energy of 60 kcal/mol (251& ...
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Chlorine
Chlorine is a chemical element with the symbol Cl and atomic number 17. The second-lightest of the halogens, it appears between fluorine and bromine in the periodic table and its properties are mostly intermediate between them. Chlorine is a yellow-green gas at room temperature. It is an extremely reactive element and a strong oxidising agent: among the elements, it has the highest electron affinity and the third-highest electronegativity on the revised Pauling scale, behind only oxygen and fluorine. Chlorine played an important role in the experiments conducted by medieval alchemists, which commonly involved the heating of chloride salts like ammonium chloride ( sal ammoniac) and sodium chloride (common salt), producing various chemical substances containing chlorine such as hydrogen chloride, mercury(II) chloride (corrosive sublimate), and hydrochloric acid (in the form of ). However, the nature of free chlorine gas as a separate substance was only recognised aroun ...
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