Borohydrides
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Borohydrides
Borohydride refers to the anion , which is also called tetrahydroborate, and its salts. Borohydride or hydroborate is also the term used for compounds containing , where ''n'' is an integer from 0 to 3, for example cyanoborohydride or cyanotrihydroborate and triethylborohydride or triethylhydroborate . Borohydrides find wide use as reducing agents in organic synthesis. The most important borohydrides are lithium borohydride and sodium borohydride, but other salts are well known (see Table). Tetrahydroborates are also of academic and industrial interest in inorganic chemistry. History Alkali metal borohydrides were first described in 1940 by Hermann Irving Schlesinger and Herbert C. Brown. They synthesized lithium borohydride from diborane : :, where M = Li, Na, K, Rb, Cs, etc. Current methods involve reduction of trimethyl borate with sodium hydride. Structure In the borohydride anion and most of its modifications, boron has a tetrahedral structure. The reactivity of the B−H ...
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Sodium Borohydride
Sodium borohydride, also known as sodium tetrahydridoborate and sodium tetrahydroborate, is an inorganic compound with the formula Na BH4. This white solid, usually encountered as an aqueous basic solution, is a reducing agent that finds application in papermaking and dye industries. It is also used as a reagent in organic synthesis. The compound was discovered in the 1940s by H. I. Schlesinger, who led a team seeking volatile uranium compounds.Hermann I Schlesinger and Herbert C Brown (1945)Preparation of alkali metal compounds. US Patent 2461661. Granted on 1949-02-15; expired on 1966-02-15. Results of this wartime research were declassified and published in 1953. Properties The compound is soluble in alcohols, certain ethers, and water, although it slowly hydrolyzes. Sodium borohydride is an odorless white to gray-white microcrystalline powder that often forms lumps. It can be purified by recrystallization from warm (50 Â°C) diglyme. Sodium borohydride is soluble ...
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Hydrogen Storage
Hydrogen storage can be accomplished by several existing methods of holding hydrogen for later use. These include mechanical approaches such as using high pressures and low temperatures, or employing chemical compounds that release H2 upon demand. While large amounts of hydrogen are produced by various industries, it is mostly consumed at the site of production, notably for the synthesis of ammonia. For many years hydrogen has been stored as compressed gas or cryogenic liquid, and transported as such in cylinders, tubes, and cryogenic tanks for use in industry or as propellant in space programs. Interest in using hydrogen for on-board storage of energy in zero-emissions vehicles is motivating the development of new methods of storage, more adapted to this new application. The overarching challenge is the very low boiling point of H2: it boils around 20.268 K (−252.882 Â°C or −423.188 Â°F). Achieving such low temperatures requires expending significant energy. Es ...
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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 reduc ...
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Cyanoborohydride
Sodium cyanoborohydride is the chemical compound with the formula Sodium, NaBoron, BHydrogen, H3cyanide, CN. It is a colourless salt, but commercial samples can appear tan. It is widely used in organic synthesis for the reduction of imines. The salt tolerates aqueous conditions. Use Owing to the presence of the electron-withdrawing cyanide substituent, [B(CN)H3]− is less reducing than is sodium borohydride, [BH4]−. As a mild reducing agent, it is used to convert imines to amines. It is especially favored for reductive aminations, wherein aldehydes or ketones are treated with an amine in the presence of this reagent: : R2CO + R'NH2 + NaBH3CN + CH3OH → R2CH-NHR' + "NaCH3OBH2CN" The reagent is typically used in excess. Selectivity is achieved at mildly basic solutions (pH 7–10). The reagent is ideal for reductive aminations ("Borch Reaction"). In conjunction with tosylhydrazine, sodium cyanoborohydride is used in the reductive deoxygenation of ketones. Structure and ...
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Lithium Borohydride
Lithium borohydride (LiBH4) is a borohydride and known in organic synthesis as a reducing agent for esters. Although less common than the related sodium borohydride, the lithium salt offers some advantages, being a stronger reducing agent and highly soluble in ethers, whilst remaining safer to handle than lithium aluminium hydride.Luca Banfi, Enrica Narisano, Renata Riva, Ellen W. Baxter, "Lithium Borohydride" e-EROS Encyclopedia of Reagents for Organic Synthesis, 2001, John Wiley & Sons. . Preparation Lithium borohydride may be prepared by the metathesis reaction, which occurs upon ball-milling the more commonly available sodium borohydride and lithium bromide: : NaBH4 + LiBr → NaBr + LiBH4 Alternatively, it may be synthesized by treating boron trifluoride with lithium hydride in diethyl ether: : BF3 + 4 LiH → LiBH4 + 3 LiF Reactions Lithium borohydride is a stronger reducing agent than sodium borohydride. In mixtures of methanol and diethyl ether, lithium borohydride is a ...
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Sodium Cyanoborohydride
Sodium cyanoborohydride is the chemical compound with the formula Sodium, NaBoron, BHydrogen, H3cyanide, CN. It is a colourless salt, but commercial samples can appear tan. It is widely used in organic synthesis for the reduction of imines. The salt tolerates aqueous conditions. Use Owing to the presence of the electron-withdrawing cyanide substituent, [B(CN)H3]− is less reducing than is sodium borohydride, [BH4]−. As a mild reducing agent, it is used to convert imines to amines. It is especially favored for reductive aminations, wherein aldehydes or ketones are treated with an amine in the presence of this reagent: : R2CO + R'NH2 + NaBH3CN + CH3OH → R2CH-NHR' + "NaCH3OBH2CN" The reagent is typically used in excess. Selectivity is achieved at mildly basic solutions (pH 7–10). The reagent is ideal for reductive aminations ("Borch Reaction"). In conjunction with tosylhydrazine, sodium cyanoborohydride is used in the reductive deoxygenation of ketones. Structure and ...
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Vitamin A
Vitamin A is a fat-soluble vitamin and an essential nutrient for humans. It is a group of organic compounds that includes retinol, retinal (also known as retinaldehyde), retinoic acid, and several provitamin A carotenoids (most notably beta-carotene ²-carotene. Vitamin A has multiple functions: it is essential for embryo development and growth, for maintenance of the immune system, and for vision, where it combines with the protein opsin to form rhodopsin the light-absorbing molecule necessary for both low-light (scotopic vision) and color vision. Vitamin A occurs as two principal forms in foods: A) retinol, found in animal-sourced foods, either as retinol or bound to a fatty acid to become a retinyl ester, and B) the carotenoids alpha-carotene, β-carotene, gamma-carotene, and the xanthophyll beta-cryptoxanthin (all of which contain β-ionone rings) that function as provitamin A in herbivore and omnivore animals which possess the enzymes that cleave and convert provi ...
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Sodium Dithionite
Sodium dithionite (also known as sodium hydrosulfite) is a white crystalline powder with a sulfurous odor. Although it is stable in dry air, it decomposes in hot water and in acid solutions. Structure The structure has been examined by Raman spectroscopy and single-crystal X-ray diffraction. The dithionite dianion has C symmetry, with almost eclipsed with a 16° O-S-S-O torsional angle. In the dihydrated form (), the dithionite anion has gauche 56° O-S-S-O torsional angle. A weak S-S bond is indicated by the S-S distance of 239 pm, which is elongated by ca. 30 pm relative to a typical S-S bond. Because this bond is fragile, the dithionite anion dissociates in solution into the O2sup>− radicals, as has been confirmed by EPR spectroscopy. It is also observed that 35S undergoes rapid exchange between S2O42− and SO2 in neutral or acidic solution, consistent with the weak S-S bond in the anion. Preparation Sodium dithionite is produced industrially by reduction of sulfur d ...
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Chloramphenicol
Chloramphenicol is an antibiotic useful for the treatment of a number of bacterial infections. This includes use as an eye ointment to treat conjunctivitis. By mouth or by injection into a vein, it is used to treat meningitis, plague, cholera, and typhoid fever. Its use by mouth or by injection is only recommended when safer antibiotics cannot be used. Monitoring both blood levels of the medication and blood cell levels every two days is recommended during treatment. Common side effects include bone marrow suppression, nausea, and diarrhea. The bone marrow suppression may result in death. To reduce the risk of side effects treatment duration should be as short as possible. People with liver or kidney problems may need lower doses. In young children a condition known as gray baby syndrome may occur which results in a swollen stomach and low blood pressure. Its use near the end of pregnancy and during breastfeeding is typically not recommended. Chloramphenicol is a broad-spectrum ...
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Thiophenicol
Thiamphenicol (also known as thiophenicol and dextrosulphenidol) is an antibiotic. It is the methyl-sulfonyl analogue of chloramphenicol and has a similar spectrum of activity, but is 2.5 to 5 times as potent. Like chloramphenicol, it is insoluble in water, but highly soluble in lipids. It is used in many countries as a veterinary antibiotic, but is available in China, Morocco and Italy for use in humans. Its main advantage over chloramphenicol is that it has never been associated with aplastic anaemia. Thiamphenicol is also widely used in Brazil, particularly for the treatment of sexually transmitted infections and pelvic inflammatory disease Pelvic inflammatory disease, also known as pelvic inflammatory disorder (PID), is an infection of the upper part of the female reproductive system, namely the uterus, fallopian tubes, and ovaries, and inside of the pelvis. Often, there may be no .... Unlike chloramphenicol, thiamphenicol is not readily metabolized in cattle, poultry, ...
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Atropine
Atropine is a tropane alkaloid and anticholinergic medication used to treat certain types of nerve agent and pesticide poisonings as well as some types of slow heart rate, and to decrease saliva production during surgery. It is typically given intravenously or by injection into a muscle. Eye drops are also available which are used to treat uveitis and early amblyopia. The intravenous solution usually begins working within a minute and lasts half an hour to an hour. Large doses may be required to treat some poisonings. Common side effects include a dry mouth, large pupils, urinary retention, constipation, and a fast heart rate. It should generally not be used in people with angle closure glaucoma. While there is no evidence that its use during pregnancy causes birth defects, that has not been well studied. It is likely safe during breastfeeding. It is an antimuscarinic (a type of anticholinergic) that works by inhibiting the parasympathetic nervous system. Atropine occurs n ...
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