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Organic Azide
An organic azide is an organic compound that contains an azide (–) functional group. Because of the hazards associated with their use, few azides are used commercially although they exhibit interesting reactivity for researchers. Low molecular weight azides are considered especially hazardous and are avoided. In the research laboratory, azides are precursors to amines. They are also popular for their participation in the " click reaction" and in Staudinger ligation. These two reactions are generally quite reliable, lending themselves to combinatorial chemistry. History Phenyl azide ("diazoamidobenzol"), was prepared in 1864 by Peter Griess by the reaction of ammonia and phenyldiazonium. In the 1890s, Theodor Curtius, who had discovered hydrazoic acid (), described the rearrangement of acyl azides to isocyanates subsequently named the Curtius rearrangement. Rolf Huisgen described the eponymous 1,3-dipolar cycloaddition. The interest in azides among organic chemists has been ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Organic Azide Resonance
Organic may refer to: * Organic, of or relating to an organism, a living entity * Organic, of or relating to an anatomical organ (anatomy), organ Chemistry * Organic matter, matter that has come from a once-living organism, is capable of decay or is the product of decay, or is composed of organic compounds * Organic compound, a compound that contains carbon ** Organic chemistry, chemistry involving organic compounds Farming, certification and products * Organic farming, agriculture conducted according to certain standards, especially the use of stated methods of fertilization and pest control * Organic certification, accreditation process for producers of organically-farmed products * Organic horticulture, the science and art of growing fruits, vegetables, flowers, or ornamental plants by following the essential principles of organic agriculture * Organic products, "organics": ** Organic food, food produced from organic farming methods and often certified organic according to orga ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Click Chemistry
In chemical synthesis, click chemistry is a class of biocompatible small molecule reactions commonly used in bioconjugation, allowing the joining of substrates of choice with specific biomolecules. Click chemistry is not a single specific reaction, but describes a way of generating products that follow examples in nature, which also generates substances by joining small modular units. In many applications, click reactions join a biomolecule and a reporter molecule. Click chemistry is not limited to biological conditions: the concept of a "click" reaction has been used in chemoproteomic, pharmacological, and various biomimetic applications. However, they have been made notably useful in the detection, localization and qualification of biomolecules. Click reactions occur in one pot, are not disturbed by water, generate minimal and inoffensive byproducts, and are "spring-loaded"—characterized by a high thermodynamic driving force that drives it quickly and irreversibly to high yi ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Tributyltin Azide
Tributyltin azide is an organotin compound with the formula (C4H9)3SnN3. It is a colorless solid although older samples can appear as yellow oils. The compound is used as a reagent in organic synthesis. Synthesis and reactions Tributyltin azide is synthesized by the salt metathesis reaction of tributyltin chloride and sodium azide. It is a reagent used in the synthesis of tetrazoles, which in turn are used to generate angiotensin II receptor antagonists. In some applications, tributyltin azide has been replaced by the less toxic trioctyltin azide and organoaluminium azides. Safety Lower alkyl In organic chemistry, an alkyl group is an alkane missing one hydrogen. The term ''alkyl'' is intentionally unspecific to include many possible substitutions. An acyclic alkyl has the general formula of . A cycloalkyl is derived from a cycloalk ... tin compounds are often highly toxic and have penetrating odors. Tributyltin azide causes skin rashes, itching or blisters.{{cite jour ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Trimethylsilyl Azide
Trimethylsilyl azide ((CH3)3SiN3) is a chemical compound used as a reagent in organic chemistry. Preparation Trimethylsilyl azide is commercially available. It may be prepared by the reaction of trimethylsilyl chloride and sodium azide: : TMSCl + NaN3 → TMSN3 + NaCl (TMS = (CH3)3Si) Applications It is considered a safer alternative to hydrazoic acid in many reactions; however, over time it will hydrolyze to hydrazoic acid, and therefore must be stored free of moisture. It has been used in the Oseltamivir total synthesis Oseltamivir total synthesis concerns the total synthesis of the antiinfluenza drug oseltamivir marketed by Hoffmann-La Roche under the trade name ''Tamiflu''. Its commercial production starts from the biomolecule shikimic acid harvested from Chines .... Safety Trimethylsilyl azide is incompatible with moisture, strong oxidizing agents, and strong acids. In 2014, a graduate student at the University of Minnesota was injured in an explosion that occurred in ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Diphenylphosphoryl Azide
Diphenylphosphoryl azide (DPPA) is an organic compound. It is widely used as a reagent in the synthesis of other organic compounds. Uses DPPA undergoes pseudohalogen replacement of the azido group by treatment with nucleophilic reagents, such as ammonia and various amines. This compound is used as a reagent for the synthesis of peptides by virtue of its reactions with carboxylic acids leading to either the urethane or the amide. The formation of the urethane is particularly valuable since it works with carboxylic acids which fail to undergo the Schmidt reaction, and is believed to involve transfer of the azido group to the carboxylic acid. It is now suggested that this reaction proceeds through the intermediate mixed anhydride, resulting from attack by the nucleophilic carboxylate anion on the phosphorus atom, with expulsion of the azide ion. The latter then attacks the carbonyl carbon atom, to give the acyl azide and loss of the diphenylphosphate anion, known to be a goo ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Alcohol (chemistry)
In chemistry, an alcohol is a type of organic compound that carries at least one hydroxyl () functional group bound to a saturated carbon atom. The term ''alcohol'' originally referred to the primary alcohol ethanol (ethyl alcohol), which is used as a drug and is the main alcohol present in alcoholic drinks. An important class of alcohols, of which methanol and ethanol are the simplest examples, includes all compounds which conform to the general formula . Simple monoalcohols that are the subject of this article include primary (), secondary () and tertiary () alcohols. The suffix ''-ol'' appears in the IUPAC chemical name of all substances where the hydroxyl group is the functional group with the highest priority. When a higher priority group is present in the compound, the prefix ''hydroxy-'' is used in its IUPAC name. The suffix ''-ol'' in non-IUPAC names (such as paracetamol or cholesterol) also typically indicates that the substance is an alcohol. However, some compou ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Sodium Nitrite
Sodium nitrite is an inorganic compound with the chemical formula NaNO2. It is a white to slightly yellowish crystalline powder that is very soluble in water and is hygroscopic. From an industrial perspective, it is the most important nitrite salt. It is a precursor to a variety of organic compounds, such as pharmaceuticals, dyes, and pesticides, but it is probably best known as a food additive used in processed meats and (in some countries) in fish products. Uses Industrial chemistry The main use of sodium nitrite is for the industrial production of organonitrogen compounds. It is a reagent for conversion of amines into diazo compounds, which are key precursors to many dyes, such as diazo dyes. Nitroso compounds are produced from nitrites. These are used in the rubber industry. It is used in a variety of metallurgical applications, for phosphatizing and detinning. Sodium nitrite is an effective corrosion inhibitor and is used as an additive in industrial greases, as an aq ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Mitsunobu Reaction
The Mitsunobu reaction is an organic reaction that converts an alcohol into a variety of functional groups, such as an ester, using triphenylphosphine and an azodicarboxylate such as diethyl azodicarboxylate (DEAD) or diisopropyl azodicarboxylate (DIAD). Although DEAD and DIAD are most commonly used, there are a variety of other azodicarboxylates available which facilitate an easier workup and/or purification and in some cases, facilitate the use of more basic nucleophiles. It was discovered by Oyo Mitsunobu (1934–2003). Typical protocol is to add the phosphine and azodicarboxylate together at −10 °C, typically in THF or toluene, until a white precipitate forms. This white, cloudy suspension is the ylide. Then a solution of the nucleophile and alcohol are added together and the reaction can be, and in many cases is, heated to reflux. The alcohol reacts with the phosphine to create a good leaving group then undergoes an inversion of stereochemistry in classic SN2 fashion ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Lithium Azide
Lithium azide is the lithium salt of hydrazoic acid. It is an unstable and toxic compound that decomposes into lithium and nitrogen when heated. Preparation It can be prepared by metathesis reaction between sodium azide and lithium nitrate or lithium sulfate solutions: : : It can also be prepared by reacting lithium sulfate with barium azide Barium azide is an inorganic azide with the formula . It is a barium salt of hydrazoic acid. Like most azides, it is explosive. It is less sensitive to mechanical shock than lead azide. Preparation Barium azide may be prepared by reacting sodiu .... : References Lithium salts Azides {{inorganic-compound-stub ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Sulfonate
In organosulfur chemistry, a sulfonate is a salt or ester of a sulfonic acid. It contains the functional group , where R is an organic group. Sulfonates are the conjugate bases of sulfonic acids. Sulfonates are generally stable in water, non-oxidizing, and colorless. Many useful compounds and even some biochemicals feature sulfonates. Sulfonate salts Anions with the general formula are called sulfonates. They are the conjugate bases of sulfonic acids with formula . As sulfonic acids tend to be strong acids, the corresponding sulfonates are weak bases. Due to the stability of sulfonate anions, the cations of sulfonate salts such as scandium triflate have application as Lewis acids. A classic preparation of sulfonates is the Strecker sulfite alkylation, in which an alkali sulfite salt displaces a halide, typically in the presence of an iodine catalyst: :RX + M2SO3 -> RSO3M + MX An alternative is the condensation of a sulfonyl halide with an alcohol in pyridine: :ROH + R' ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Tosyl Group
In organic chemistry, a toluenesulfonyl group (tosyl group, abbreviated Ts or Tos) is a univalent functional group with the chemical formula –. It consists of a tolyl group, –, joined to a sulfonyl group, ––, with the open valence on sulfur. This group is usually derived from the compound tosyl chloride, (abbreviated TsCl), which forms esters and amides of toluenesulfonic acid, (abbreviated TsOH). The para orientation illustrated (''p''-toluenesulfonyl) is most common, and by convention ''tosyl'' without a prefix refers to the ''p''-toluenesulfonyl group. The toluenesulfonate (or tosylate) group refers to the – (TsO–) group, with an additional oxygen attached to sulfur and open valence on an oxygen. In a chemical name, the term ''tosylate'' may either refer to the salts containing the anion of ''p''-toluenesulfonic acid, (M = alkali metal, , , etc), or it may refer to esters of ''p''-toluenesulfonic acid, TsOR (R = organyl group). Applications For SN2 reacti ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
