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Ishikawa Reagent
Ishikawa's reagent is a fluorinating reagent used in organic chemistry. It is used to convert alcohols into alkyl fluorides and carboxylic acids into acyl fluorides. Aldehydes and ketones do not react with it. The reagent consists of a mixture of ''N'',''N''-diethyl-(1,1,2,3,3,3-hexafluoropropyl)amine and ''N'',''N''-diethyl-(''E'')-pentafluoropropenylamine in varying proportions. The active species is the hexafluoropropylamine; any enamine is converted into this by the hydrogen fluoride byproduct as the reaction proceeds. Ishikawa's reagent is a popular alternative to the DAST reagent, since it is shelf-stable and easily prepared from inexpensive and innocuous reagents. It is an improvement on Yarovenko's reagent, the adduct of chlorotrifluoroethylene and diethylamine, which must be prepared in a sealed vessel and once prepared keeps only for a few days, even in the refrigerator. The reagent is mostly used to convert primary alcohols to alkyl fluorides under mild conditions wit ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Ishikawa Reagent
Ishikawa's reagent is a fluorinating reagent used in organic chemistry. It is used to convert alcohols into alkyl fluorides and carboxylic acids into acyl fluorides. Aldehydes and ketones do not react with it. The reagent consists of a mixture of ''N'',''N''-diethyl-(1,1,2,3,3,3-hexafluoropropyl)amine and ''N'',''N''-diethyl-(''E'')-pentafluoropropenylamine in varying proportions. The active species is the hexafluoropropylamine; any enamine is converted into this by the hydrogen fluoride byproduct as the reaction proceeds. Ishikawa's reagent is a popular alternative to the DAST reagent, since it is shelf-stable and easily prepared from inexpensive and innocuous reagents. It is an improvement on Yarovenko's reagent, the adduct of chlorotrifluoroethylene and diethylamine, which must be prepared in a sealed vessel and once prepared keeps only for a few days, even in the refrigerator. The reagent is mostly used to convert primary alcohols to alkyl fluorides under mild conditions wit ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Alcohols
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 compound ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Carboxylic Acids
In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group () attached to an R-group. The general formula of a carboxylic acid is or , with R referring to the alkyl, alkenyl, aryl, or other group. Carboxylic acids occur widely. Important examples include the amino acids and fatty acids. Deprotonation of a carboxylic acid gives a carboxylate anion. Examples and nomenclature Carboxylic acids are commonly identified by their trivial names. They at oftentimes have the suffix ''-ic acid''. IUPAC-recommended names also exist; in this system, carboxylic acids have an ''-oic acid'' suffix. For example, butyric acid (C3H7CO2H) is butanoic acid by IUPAC guidelines. For nomenclature of complex molecules containing a carboxylic acid, the carboxyl can be considered position one of the parent chain even if there are other substituents, such as 3-chloropropanoic acid. Alternately, it can be named as a "carboxy" or "carboxylic acid" substituent on another ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Acyl Fluoride
In organic chemistry, an acyl halide (also known as an acid halide) is a chemical compound derived from an oxoacid by replacing a hydroxyl group () with a halide group (, where X is a halogen). If the acid is a carboxylic acid (), the compound contains a functional group, which consists of a carbonyl group () singly bonded to a halogen atom. The general formula for such an acyl halide can be written RCOX, where R may be, for example, an alkyl group, CO is the carbonyl group, and X represents the halide, such as chloride. Acyl chlorides are the most commonly encountered acyl halides, but acetyl iodide is the one produced (transiently) on the largest scale. Billions of kilograms are generated annually in the production of acetic acid. Preparation Aliphatic acyl halides On an industrial scale, the reaction of acetic anhydride with hydrogen chloride produces a mixture of acetyl chloride and acetic acid: :(CH3CO)2O + HCl -> CH3COCl + CH3CO2H Common syntheses of acyl chlorides als ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Aldehydes
In organic chemistry, an aldehyde () is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred to as an aldehyde but can also be classified as a formyl group. Aldehydes are common and play important roles in the technology and biological spheres. Structure and bonding Aldehydes feature a carbon center that is connected by a double bond to oxygen and a single bond to hydrogen and single bond to a third substituent, which is carbon or, in the case of formaldehyde, hydrogen. The central carbon is often described as being sp2- hybridized. The aldehyde group is somewhat polar. The C=O bond length is about 120-122 picometers. Physical properties and characterization Aldehydes have properties that are diverse and that depend on the remainder of the molecule. Smaller aldehydes are more soluble in water, formaldehyde and acetaldehyde completely so. The volatile aldehydes have pungent odors. Aldehy ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Ketones
In organic chemistry, a ketone is a functional group with the structure R–C(=O)–R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group –C(=O)– (which contains a carbon-oxygen double bond C=O). The simplest ketone is acetone (where R and R' is methyl), with the formula . Many ketones are of great importance in biology and in industry. Examples include many sugars (ketoses), many steroids (e.g., testosterone), and the solvent acetone. Nomenclature and etymology The word ''ketone'' is derived from ''Aketon'', an old German word for ''acetone''. According to the rules of IUPAC nomenclature, ketone names are derived by changing the suffix ''-ane'' of the parent alkane to ''-anone''. Typically, the position of the carbonyl group is denoted by a number, but traditional nonsystematic names are still generally used for the most important ketones, for example acetone and benzophenone. These nonsystematic names are considered ret ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Enamine
An enamine is an unsaturated compound derived by the condensation of an aldehyde or ketone with a secondary amine. Enamines are versatile intermediates. : The word "enamine" is derived from the affix ''en''-, used as the suffix of alkene, and the root ''amine''. This can be compared with enol, which is a functional group containing both alkene (''en''-) and alcohol (-''ol''). Enamines are considered to be nitrogen analogs of enols. If one of the nitrogen substituents is a hydrogen atom, H, it is the tautomeric form of an imine. This usually will rearrange to the imine; however there are several exceptions (such as aniline). The enamine-imine tautomerism may be considered analogous to the keto-enol tautomerism. In both cases, a hydrogen atom switches its location between the heteroatom (oxygen or nitrogen) and the second carbon atom. Enamines are both good nucleophiles and good bases. Their behavior as carbon-based nucleophiles is explained with reference to the following reson ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Hydrogen Fluoride
Hydrogen fluoride (fluorane) is an inorganic compound with the chemical formula . This colorless gas or liquid is the principal industrial source of fluorine, often as an aqueous solution called hydrofluoric acid. It is an important feedstock in the preparation of many important compounds including pharmaceuticals and polymers, e.g. polytetrafluoroethylene (PTFE). HF is widely used in the petrochemical industry as a component of superacids. Hydrogen fluoride boils at near room temperature, much higher than other hydrogen halides. Hydrogen fluoride is an extremely dangerous gas, forming corrosive and penetrating hydrofluoric acid upon contact with moisture. The gas can also cause blindness by rapid destruction of the corneas. History In 1771 Carl Wilhelm Scheele prepared the aqueous solution, hydrofluoric acid in large quantities, although hydrofluoric acid had been known in the glass industry before then. French chemist Edmond Frémy (1814–1894) is credited with discoveri ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Diethylaminosulfur Trifluoride
Diethylaminosulfur trifluoride (DAST) is the organosulfur compound with the formula Et2NSF3. This liquid is a fluorinating reagent used for the synthesis of organofluorine compounds. The compound is colourless; older samples assume an orange colour. Use in organic synthesis DAST converts alcohols to the corresponding alkyl fluorides as well as aldehydes and unhindered ketones to geminal difluorides. Carboxylic acids react no further than the acyl fluoride (sulfur tetrafluoride effects the transformation —CO2H → —CF3). DAST is used in preference to the more classical gaseous SF4, since as a liquid it is more easily handled. A slightly thermally more stable compound is morpho-DAST. Acid-labile substrates are less likely to undergo rearrangement and elimination since DAST is less prone to contamination with acids. Reaction temperatures are milder as well – alcohols typically react at −78 °C and ketones around 0 °C. Synthesis DAST is prepared by the reaction of ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Chlorotrifluoroethylene
Chlorotrifluoroethylene (CTFE) is a chlorofluorocarbon with chemical formula CFCl=CF2. It is commonly used as a refrigerant in cryogenic applications. CTFE has a carbon-carbon double bond and so can be polymerized to form polychlorotrifluoroethylene or copolymerized to produce the plastic ECTFE. PCTFE has the trade name Neoflon PCTFE from Daikin Industries in Japan, and it used to be produced under the trade name Kel-F from 3M Corporation in Minnesota. Production and reactions Chlorotrifluoroethylene is produced commercially by the dechlorination of 1,1,2-trichloro-1,2,2-trifluoroethane with zinc: :CFCl2-CF2Cl + Zn → CClF=CF2 + ZnCl2 In 2012, an estimated 1–10 million pounds were produced commercially in the United States. The thermal dimerization of chlorotrifluoroethylene gives 1,2-dichloro-1,2,3,3,4,4-hexafluorocyclobutane. Dichlorination of the latter gives hexafluorocyclobutene Hexafluorocyclobutene is the organofluorine compound with the formula (CF2)2(CF)2. ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Diethylamine
Diethylamine is an organic compound with the formula (CH3CH2)2NH. It is a secondary amine. It is a flammable, weakly alkaline liquid that is miscible with most solvents. It is a colorless liquid, but commercial samples often appear brown due to impurities. It has a strong ammonia-like odor. Production and uses Diethylamine is made by the alumina-catalyzed reaction of ethanol and ammonia. It is obtained together with ethylamine and triethylamine. Annual production of three ethylamines was estimated in 2000 to be 80,000,000 kg. It is used in the production of corrosion inhibitor ''N'',''N''- diethylaminoethanol, by reaction with ethylene oxide. It is also a precursor to a wide variety of other commercial products. Diethylamine is also sometimes used in the illicit production of LSD. Supramolecular structure Diethylamine is the smallest and simplest molecule that features a supramolecular helix as its lowest energy aggregate. Other similarly sized hydrogen-bonding In c ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Hexafluoropropene
Hexafluoropropylene is the fluoroalkene with the formula CF3CF=CF2. It is the perfluorocarbon counterpart to the hydrocarbon propylene. It is mainly used to produce copolymers with tetrafluoroethylene. Hexafluoropropylene is used as a chemical intermediate. Preparation Hexafluoropropylene can be produced by pyrolysis of tetrafluoroethylene: :3CF2=CF2 → 2CF3CF=CF2 It can also be prepared from chlorodifluoromethane, or produced from various chlorofluorocarbons Chlorofluorocarbons (CFCs) and hydrochlorofluorocarbons (HCFCs) are fully or partly halogenated hydrocarbons that contain carbon (C), hydrogen (H), chlorine (Cl), and fluorine (F), produced as volatile derivatives of methane, ethane, and propan .... References Fluorocarbons Haloalkenes {{organohalide-stub ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
