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Triazene Cleavage
200px, melanoma.html" ;"title="Dacarbazine is a triazene used in the treatment of melanoma">Dacarbazine is a triazene used in the treatment of melanoma and Hodgkin's lymphoma. Triazenes are organic compounds that contain the functional group R1−N=N−NR2R3, where the R are each any of various types of substituent groups. Some medications and dyes are triazenes. Formally, the triazenes are related to the unstable chemical triazene, H2N−N=NH. Production Triazenes are prepared from the ''N''-coupling reaction between diazonium salts and primary or secondary amines. The coupling reactions are typically mild, using a base such as sodium acetate, sodium carbonate, or sodium bicarbonate. The diazonium reagents are themselves available starting from amines. For symmetrical triazenes derived from primary amines, partial diazotization gives a mixture of the original amine and its diazo derivative that then couple with each other. For example, 1,3-diphenyltriazene (PhN=N−NHPh) can be ...
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Dacarbazine
Dacarbazine, also known as imidazole carboxamide and sold under the brand name DTIC-Dome, is a chemotherapy medication used in the treatment of melanoma and Hodgkin's lymphoma. For Hodgkin's lymphoma, it is often used together with vinblastine, bleomycin, and doxorubicin. It is given by injection into a vein. Common side effects include loss of appetite, vomiting, low white blood cell count, and low platelets. Other serious side effects include liver problems and allergic reactions. It is unclear if use in pregnancy is safe for the baby. Dacarbazine is in the alkylating agent and purine analog families of medication. Dacarbazine was approved for medical use in the United States in 1975. It is on the World Health Organization's List of Essential Medicines. Medical uses As of mid-2006, dacarbazine is commonly used as a single agent in the treatment of metastatic melanoma, and as part of the ABVD chemotherapy regimen to treat Hodgkin's lymphoma, and in the MAID regimen fo ...
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Primary Amine
In chemistry, amines (, ) are organic compounds that contain carbon-nitrogen bonds. Amines are formed when one or more hydrogen atoms in ammonia are replaced by alkyl or aryl groups. The nitrogen atom in an amine possesses a lone pair of electrons. Amines can also exist as hetero cyclic compounds. Aniline is the simplest aromatic amine, consisting of a benzene ring bonded to an amino group. Amines are classified into three types: primary (1°), secondary (2°), and tertiary (3°) amines. Primary amines (1°) contain one alkyl or aryl substituent and have the general formula RNH2. Secondary amines (2°) have two alkyl or aryl groups attached to the nitrogen atom, with the general formula R2NH. Tertiary amines (3°) contain three substituent groups bonded to the nitrogen atom, and are represented by the formula R3N. The functional group present in primary amines is called the amino group. Classification of amines Amines can be classified according to the nature and number o ...
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Coumarin
Coumarin () or 2''H''-chromen-2-one is an aromatic organic chemical compound with formula . Its molecule can be described as a benzene molecule with two adjacent hydrogen atoms replaced by an unsaturated lactone ring , forming a second six-membered heterocycle that shares two carbons with the benzene ring. It belongs to the benzopyrone chemical class and is considered a lactone. Coumarin is a colorless crystalline solid with a sweet odor resembling the scent of vanilla and a bitter taste. It is found in many plants, where it may serve as a chemical defense against predators. While coumarin is not an anticoagulant, its 3-alkyl-4-hydroxy derivatives, such as the fungal metabolite dicoumarol, inhibit synthesis of vitamin K, a key component in blood clotting. A related compound, the prescription drug anticoagulant warfarin, is used to inhibit formation of blood clots, deep vein thrombosis, and pulmonary embolism. Etymology Coumarin is derived from , the French word for the ...
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Lactam
A lactam is a Cyclic compound, cyclic amide, formally derived from an amino alkanoic acid through cyclization reactions. The term is a portmanteau of the words ''lactone'' + ''amide''. Nomenclature Greek_alphabet#Letters, Greek prefixes in alphabetical order indicate ring size. This ring-size nomenclature stems from the fact that hydrolysis of an α-lactam gives an α-amino acid and that of a β-Lactam gives a β-amino acid, and so on. Synthesis General synthetic methods are used for the organic synthesis of lactams. Beckmann rearrangement Lactams form by the Acid catalysis, acid-catalyzed Rearrangement reaction, rearrangement of oximes in the Beckmann rearrangement. Schmidt reaction Lactams form from cyclic ketones and hydrazoic acid in the Schmidt reaction. Cyclohexanone with hydrazoic acid, forms Caprolactam, ε - Caprolactum, which upon treatment with excess acid forms Pentylenetetrazol, Cardiazole, a heart stimulant. Cyclization of amino acids Lactams can be formed fr ...
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Cinnoline
Cinnoline is an aromatic heterocyclic compound with the formula C8H6N2. It is isomeric with other naphthyridines including quinoxaline, phthalazine and quinazoline. Properties The free base can be obtained as an oil by treatment of the hydrochloride with base. It co-crystallizes with one molecule of ether as white silky needles, (m.p. 24–25 °C) upon cooling ethereal solutions. The free base melts at 39 °C. It has a taste resembling that of chloral hydrate and leaves a sharp irritation for some time. Discovery and synthesis The compound was first obtained in impure form by cyclization of the alkyne ''o''-C6H4(N2Cl)C≡CCO2H in water to give 4-hydroxycinnoline-3-carboxylic acid. This material could be decarboxylated and the hydroxyl group reductively removed to give the parent heterocycle. This reaction is called the Richter cinnoline synthesis. Improved methods exist for its synthesis. It can be prepared by dehydrogenation of dihydrocinnoline with ...
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Secondary Amine
In chemistry, amines (, ) are organic compounds that contain carbon-nitrogen bonds. Amines are formed when one or more hydrogen atoms in ammonia are replaced by alkyl or aryl groups. The nitrogen atom in an amine possesses a lone pair of electrons. Amines can also exist as hetero cyclic compounds. Aniline is the simplest aromatic amine, consisting of a benzene ring bonded to an amino group. Amines are classified into three types: primary (1°), secondary (2°), and tertiary (3°) amines. Primary amines (1°) contain one alkyl or aryl substituent and have the general formula RNH2. Secondary amines (2°) have two alkyl or aryl groups attached to the nitrogen atom, with the general formula R2NH. Tertiary amines (3°) contain three substituent groups bonded to the nitrogen atom, and are represented by the formula R3N. The functional group present in primary amines is called the amino group. Classification of amines Amines can be classified according to the nature and number o ...
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Protecting Group
A protecting group or protective group is introduced into a molecule by chemical modification of a functional group to obtain chemoselectivity in a subsequent chemical reaction. It plays an important role in multistep organic synthesis. In many preparations of delicate organic compounds, specific parts of the molecules cannot survive the required reagents or chemical environments. These parts (functional groups) must be protected. For example, lithium aluminium hydride is a highly reactive reagent that usefully reduces esters to alcohols. It always reacts with carbonyl groups, and cannot be discouraged by any means. When an ester must be reduced in the presence of a carbonyl, hydride attack on the carbonyl must be prevented. One way to do so converts the carbonyl into an acetal, which does not react with hydrides. The acetal is then called a protecting group for the carbonyl. After the hydride step is complete, aqueous acid removes the acetal, restoring the carbonyl. This step ...
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Thiophenol
Thiophenol is an organosulfur compound with the formula C6H5SH, sometimes abbreviated as PhSH. This foul-smelling colorless liquid is the simplest aromatic thiol. The chemical structures of thiophenol and its derivatives are analogous to phenols, where the oxygen atom in the hydroxyl group (−OH) bonded to the aromatic ring in phenol is replaced by a sulfur atom. The prefix thio- implies a sulfur-containing compound and when used before a root word name for a compound which would normally contain an oxygen atom, in the case of 'thiol' that the alcohol oxygen atom is replaced by a sulfur atom. Thiophenols also describes a class of compounds formally derived from thiophenol itself. All have a sulfhydryl group (-SH) covalently bonded to an aromatic ring. The organosulfur ligand in the medicine thiomersal is a thiophenol. Synthesis There are several methods of synthesis for thiophenol and related compounds, although thiophenol itself is usually purchased for laboratory oper ...
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Sodium Sulfide
Sodium sulfide is a chemical compound with the formula Na2 S, or more commonly its hydrate Na2S·9 H2O. Both the anhydrous and the hydrated salts are colorless solids, although technical grades of sodium sulfide are generally yellow to brick red owing to the presence of polysulfides. It is commonly supplied as a crystalline mass, in flake form, or as a fused solid. They are water-soluble, giving strongly alkaline solutions. When exposed to moisture, Na2S immediately hydrates to give sodium hydrosulfide. Sodium sulfide has an unpleasant rotten egg smell due to the hydrolysis to hydrogen sulfide in moist air. Some commercial samples are described as Na2S·''x''H2O, where a weight percentage of Na2S is specified. Commonly available grades have around 60% Na2S by weight, which means that ''x'' is around 3. These grades of sodium sulfide are often marketed as 'sodium sulfide flakes'. These samples consist of NaSH, NaOH, and water. Structure The structures of sodium sulfides have bee ...
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Diazonium
Diazonium compounds or diazonium salts are a group of organic compounds sharing a common functional group where R can be any organic group, such as an alkyl or an aryl, and X is an inorganic or organic anion, such as a halide. The parent, compound where R is hydrogen, is diazenylium. Structure and general properties Arene derivatives According to X-ray crystallography the linkage is linear in typical diazonium salts. The bond distance in benzenediazonium tetrafluoroborate is 1.083(3)  Å, which is almost identical to that for dinitrogen molecule (N≡N). The linear free energy constants σm and σp indicate that the diazonium group is strongly electron-withdrawing. Thus, the diazonio-substituted phenols and benzoic acids have greatly reduced p''K''a values compared to their unsubstituted counterparts. The p''K''a of phenolic proton of 4-hydroxybenzenediazonium is 3.4, versus 9.9 for phenol itself. In other words, the diazonium group raises the ionization constant ''K''a ...
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Quaternary Amine
In organic chemistry, quaternary ammonium cations, also known as quats, are positively-charged polyatomic ions of the structure , where R is an alkyl group, an aryl group or organyl group. Unlike the ammonium ion () and the primary, secondary, or tertiary ammonium cations, the quaternary ammonium cations are permanently charged, independent of the pH of their solution. Quaternary ammonium salts or quaternary ammonium compounds (called quaternary amines in oilfield parlance) are salts of quaternary ammonium cations. Polyquats are a variety of engineered polymer forms which provide multiple quat molecules within a larger molecule. Quats are used in consumer applications including as antimicrobials (such as detergents and disinfectants), fabric softeners, and hair conditioners. As an antimicrobial, they are able to inactivate enveloped viruses (such as SARS-CoV-2). Quats tend to be gentler on surfaces than bleach-based disinfectants, and are generally fabric-safe. Synthesis Q ...
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Triazene 1
Triazene is an unsaturated inorganic compound having the chemical formula N3 H3. It has one double bond and is the second-simplest member of the azene class of hydronitrogen compounds, after diimide. Triazenes are a class of organic compounds containing the functional group −N(H)−N=N−. Triazene, possibly along with its isomer triimide (HNNHNH), has been synthesized in electron-irradiated ices of ammonia and ammonia/dinitrogen and detected in the gas phase after sublimation. References External links *IUPAC Gold Book The International Union of Pure and Applied Chemistry (IUPAC) publishes many books which contain its complete list of definitions. The definitions are divided initially into seven IUPAC Colour Books: Gold, Green, Blue, Purple, Orange, White, and R ...br>definition {{Hydrides by group Nitrogen hydrides ...
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