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Pentafluorophenol
Pentafluorophenol is the organofluorine compound (specifically a fluoroalcohol) with the formula C6F5OH. This is the perfluorinated analogue of phenol. It is a white odorless solid that melts just above room temperature. With a pKa of 5.5, it is one of the most acidic phenols. Uses Pentafluorophenol is used to prepare pentafluorophenyl esters, which are active esters useful in peptide synthesis In organic chemistry, peptide synthesis is the production of peptides, compounds where multiple amino acids are linked via amide bonds, also known as peptide bonds. Peptides are chemically synthesized by the condensation reaction of the carboxy .... Environmental hazards Pentafluorophenol is considered hazardous because of oral, dermal and inhalation toxicity and because it causes "severe skin burns and eye damage." References {{Reflist Fluoroarenes Perfluorinated compounds Phenols ...
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Perfluorinated Compounds
A perfluorinated compound (PFC) or perfluoro compound is an organofluorine compound containing only carbon-fluorines and C−C bonds, as well as potentially heteroatoms. Perfluorinated compounds have properties that result from the presence of fluorocarbons (containing only C−F and C−C bonds) and any functional group. Common functional groups in PFCs are OH, CO2H, chlorine, O, and SO3H. Electrofluorination is the predominant method of production. Some of these compounds known as perfluoroalkanes can remain in our atmosphere for a long time. They bioaccumulate due to their chemical stability. Because of their potential contribution to climate change, they were regulated under the Kyoto Protocol. Some fluorosurfactants have proven toxic in animal testing while widespread industrial applications continue. Applications Perfluorinated compounds are used ubiquitously: For example, fluorosurfactants are widely used in the production of teflon (PTFE) and related fluorinated po ...
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Organofluorine Compound
Organofluorine chemistry describes the chemistry of the organofluorines, organic compounds that contain the carbon–fluorine bond. Organofluorine compounds find diverse applications ranging from oil and water repellents to pharmaceuticals, refrigerants, and reagents in catalysis. In addition to these applications, some organofluorine compounds are pollutants because of their contributions to ozone depletion, global warming, bioaccumulation, and toxicity. The area of organofluorine chemistry often requires special techniques associated with the handling of fluorinating agents. The carbon–fluorine bond Fluorine has several distinctive differences from all other substituents encountered in organic molecules. As a result, the physical and chemical properties of organofluorines can be distinctive in comparison to other organohalogens. # The carbon–fluorine bond is one of the strongest in organic chemistry (an average bond energy around 480 kJ/molKirsch, Peer ''Modern flu ...
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Fluoroalcohol
Fluoroalcohols are organofluorine compounds consisting of an alcohol functional group with at least one C-F bond. These compounds often have distinctive solvent properties. Perfluoroalcohols Most primary and secondary perfluoroalcohols are unstable, for example trifluoromethanol eliminates hydrogen fluoride, forming carbonyl fluoride. This reaction is reversible. : ⇌ + {{chem, H, F (I) Stable perfluorinated alcohols include nonafluoro-tert-butyl alcohol ((CF3)3COH) and pentafluorophenol (C6F5OH). Partially fluorinated alcohols Numerous partially fluorinated alcohols are known. Trifluoroethanol is a popular solvent. Fluorotelomer alcohols are precursors to perfluorocarboxylic acids. Pirkle's alcohol is used a chiral shift reagent in nuclear magnetic resonance spectroscopy Nuclear magnetic resonance spectroscopy, most commonly known as NMR spectroscopy or magnetic resonance spectroscopy (MRS), is a spectroscopic technique to observe local magnetic fields around ato ...
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Phenol
Phenol (also called carbolic acid) is an aromatic organic compound with the molecular formula . It is a white crystalline solid that is volatile. The molecule consists of a phenyl group () bonded to a hydroxy group (). Mildly acidic, it requires careful handling because it can cause chemical burns. Phenol was first extracted from coal tar, but today is produced on a large scale (about 7 billion kg/year) from petroleum-derived feedstocks. It is an important industrial commodity as a precursor to many materials and useful compounds. It is primarily used to synthesize plastics and related materials. Phenol and its chemical derivatives are essential for production of polycarbonates, epoxies, Bakelite, nylon, detergents, herbicides such as phenoxy herbicides, and numerous pharmaceutical drugs. Properties Phenol is an organic compound appreciably soluble in water, with about 84.2 g dissolving in 1000 mL (0.895 M). Homogeneous mixtures of phenol and water ...
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Pentafluorophenyl Esters
Pentafluorophenyl (PFP) esters are chemical compounds with the generic formula RC(O)OC6F5. They are active esters derived from pentafluorophenol (HOC6F5). PFP esters are useful for attaching fluorophores such as fluorescein or haptens to primary amines in biomolecules. They also are valuable in laboratory peptide synthesis In organic chemistry, peptide synthesis is the production of peptides, compounds where multiple amino acids are linked via amide bonds, also known as peptide bonds. Peptides are chemically synthesized by the condensation reaction of the carboxy .... Pentafluorophenyl esters produce amide bonds as effectively as succinimidyl esters and various similar agents do, but PFP esters are particularly useful because they are less susceptible to spontaneous hydrolysis during conjugation reactions. References {{Reflist Esters Pentafluorophenyl compounds Phenol esters Reagents for organic chemistry ...
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Active Ester
In organic chemistry, an active ester is an ester functional group that is highly susceptible toward nucleophilic attack. Activation can be imparted by modifications of the acyl or the alkoxy components of a normal ester, say ethyl acetate. Typical modifications call for electronegative substituents. Active esters are employed in both synthetic and biological chemistry. Reactivity Active esters are mainly used as acylating agents. They undergo the same reactions as their unactivated analogues but do so more rapidly. They are prone to hydrolysis, for example. Of great interest is the enhanced reactivity of active esters toward amines to give amides. Examples Thioesters are prominent active esters, as illustrated by the esters of coenzyme A. In synthetic chemistry, active esters include derivatives of nitrophenols and pentafluorophenol. Active esters are often used in peptide synthesis, e.g., N-hydroxysuccinimide, hydroxybenzotriazole. Active esters of acrylic acid are precur ...
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Peptide Synthesis
In organic chemistry, peptide synthesis is the production of peptides, compounds where multiple amino acids are linked via amide bonds, also known as peptide bonds. Peptides are chemically synthesized by the condensation reaction of the carboxyl group of one amino acid to the amino group of another. Protecting group strategies are usually necessary to prevent undesirable side reactions with the various amino acid side chains. Chemical peptide synthesis most commonly starts at the carboxyl end of the peptide (C-terminus), and proceeds toward the amino-terminus (N-terminus). Protein biosynthesis (long peptides) in living organisms occurs in the opposite direction. The chemical synthesis of peptides can be carried out using classical solution-phase techniques, although these have been replaced in most research and development settings by solid-phase methods (see below). Solution-phase synthesis retains its usefulness in large-scale production of peptides for industrial purposes how ...
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