Lithium aluminum hydride is a reactive chemical and an explosion hazard. Lah, lithium alanate, lithium tetrahydroaluminate cas number 16853853. Since this is an s n 2 reaction using a strong base, it works well only for unhindered 1 and methyl substrates. Files are available under licenses specified on their description page. Reductions by the alumino and borohydrides in organic synthesis.
If inhaled if breathed in, move person into fresh air. Reacts vigorously with hydroxy compounds such as water, alcohols, carboxylic acids mellor 2 supp. It was discovered by finholt, bond and schlesinger in 1947. Use the link below to share a fulltext version of this article with your friends and colleagues.
Conjugate addition reactions factors that favour the process 5 since the conjugate addition is performed under protic. Since this is an s n 2 reaction using a strong base, it works well only for. Lithium aluminium hydride lialh4, lah, lithal is a widely used reducing agent. Safety operating procedure template by signing and dating here the principal investigator or a designee certifies that the safety operating procedure sop for lithium aluminum hydride is accurate and effectively provides guidance for employees and students in this lab. Procedures for safe use of pyrophoric solids, 22009 page 3 of 4 specific recommendations for working with pyrophoric solid reagents lithium aluminum hydride reacts violently with water and has a significant heat of solvation. Two alcohols are formed in this reaction, one derived from the acyl group of the ester 2. Alkyl halides and epoxides are reduced by the hydride reagent lithium aluminum hydride lialh 4.
Reason for citation lithium aluminum hydride is on the hazardous. Lithium aluminum hydride lialh4 carbonyl reduction. Lithium aluminum hydride powder, reagent grade, 95%. Hydride compounds are used often used as portable sources of hydrogen gas. Page 1 of 7 lithium aluminium hydride cas no 16853853 material safety data sheet sdsmsds section 1. Reduction of esters with this reagent, like the reduction of carboxylic acids, gives primary alcohols. Indeed, it will reduce almost any molecule that bears a heteroatom. Lialh4 lah is a powerful and rather nonselective hydride transfer reagent that readily reduces carboxylic acids, esters, lactones, anhydrides, amides and nitriles to the corresponding alcohols or amines. Dibalh, lah, nah metal hydrides how to use and quench. Sigmaaldrich offers a number of lithium aluminum hydride products. A campus laboratory fire involving lithium aluminum hydride.
Lithium aluminum hydrideboron trifluoride etherate. Pdf lithium aluminum hydride lialh4 is an interesting high capacity hydrogen storage material with fast hydrogen release kinetics when mechanically. There is a tetrahedral arrangement of hydrogens around aluminium in aluminium hydride, alh 4ion. A reduction with lithium aluminum hydride takes place in a general twostep synthesis. The reaction was first introduced into the organic chemistry laboratories here at imperial college decades ago, vanished for a short period, and has recently been reintroduced again. Et 3al, et 2alcl, etalcl 2, me 3al, diethylethoxyaluminium grignard reagents. It is used in making drugs, polymers, and other organic chemicals. Super tricks to handle and quenching of lah lithium aluminum hydride, dibalh diisobutyl aluminium hydride, nah sodium hydride in organic synthesis. Lithium aluminium hydride, 1m solution in thf revision date 19jan2018 6.
Similar to other metastable hydrides, lialh 4 does not form by direct hydrogenation at reasonable hydrogen pressures. Lithium aluminium hydride, commonly abbreviated to lah, is an inorganic compound with the chemical formula lialh 4. Regeneration of lithium aluminum hydride brookhaven national. Pyrophoric lab chemicals ucla chemistry and biochemistry. Identification lithium aluminum hydride is a white to grey powder. Reduction to alcohols lialh4 reduction to alcohols lialh4 definition. Mechanism of the lithal lah reduction of cinnamaldehyde. Aziridine formation by lithium aluminum hydride reduction of oximes. Lithium aluminum hydride is a remarkably powerful reducing agent. Aziridine formation by lithium aluminum hydride reduction of ketoximes of bridged ring systems. Safe working procedure for lithium aluminium hydride. Lithium aluminum hydride, pellets safety data sheet 07242015 en english us sds id. Both of these factors combine to make lithium aluminium hydride a more powerful reducing agent than sodium borohydride.
When treated with lithium aluminum hydride abbreviated lah, esters are reduced to yield primary alcohols. Lithium aluminum hydride lialh 4 is a promising compound for hydrogen storage, with a high gravimetric and volumetric hydrogen density and a low decomposition temperature. Reduction of esters to primary alcohols lithium aluminum hydride reduces all carboxylic acid derivatives. Handle lah and other pyrophorics under an inert atmosphere, within a glove box, fume hood, or equivalent. Lithium aluminium hydride, lialh4, also abbreviated as lah, is a reducing agent commonly employed in modern organic synthesis. Show this safety data sheet to the doctor in attendance. American elements offers a broad range of products for hydrogen storage research, advanced fuel cells and battery applications. Lithium aluminum hydride is used as a reducing agent in various synthetic organic chemistry reactions. Lithium aluminum hydride appears as a white powder that turns gray on standing. The procedure is intricate, attention must be given to the removal of lithium chloride. It is not possible to produce tertiary alcohols with this method of reduction. Conjugate addition reactions factors that favour the process 5 since the conjugate addition is.
This compound is used as a reducing agent in organic synthesis, especially for the reduction of esters, carboxylic acids, and amides. Aldehydes, ketones, epoxides, and several other functional groups can also be reduced by lithium borohydride. Incompatibility of common laboratory chemicals when certain hazardous chemicals are stored or mixed together, violent reactions may occur because the chemicals are. Two practical sources of hydride like reactivity are the complex metal hydrides lithium aluminum hydride lialh 4 and sodium borohydride nabh 4. Lithium aluminium hydride lialh4 or alh4li cid 21226445 structure, chemical names. It is a nucleophilic reducing agent, best used to reduce polar multiple bonds like co. Lithium aluminum hydride lithium aluminum hydride, ethereal lithium borohydride lithium ferrosilicon lithium hydride lithium hydride, fused solid lithium nitride lithium silicon magnesium alkyls magnesium aluminum phosphide magnesium granules, coated, particle size not less than 149 microns. Lithium aluminum hydride lialh4 is a promising compound for hydrogen storage, with a high gravimetric and volumetric hydrogen density and a low. Further, nothing contained herein shall be taken as an inducement or recommendation to manufacture or use any of the herein materials or. As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters 150 feet for liquids and at least 25 meter 75 feet for solids. In addition to reducing aldehydes and ketones like nabh4, lialh4 will also reduce carboxylic acids and carboxyl derivatives.
Safe working procedure for lithium aluminium hydride lithium aluminium hydride lialh4, laii, lithal is a widely used reducing agent. Material safety data sheet section 1 lithium aluminium hydride 1 chemical product and company identification msds name. Lithium aluminium hydride, commonly abbreviated to lah, is an inorganic compound with the chemical formula lialh4. Therefore, there is little need for a more powerful reducing agent, which would presumably be generated if alkylated reagents e. Lithium aluminum hydride powder, reagent grade, 95% synonym. Lithium aluminum hydride lialh4 is the stronger common carbonyl reducing agent. General handling and storage of lithium aluminum hydride. The reduction of cinnamaldehyde by lithium aluminium hydride lah was reported in a classic series of experiments, dating from 19478. Rmgx ralkyl, aryl, vinyl xhalogen lithium reagents. Aluminium hydride is prepared by treating lithium aluminium hydride with aluminium trichloride. All structured data from the file and property namespaces is available under the creative commons cc0 license. Reduction of carbonyls to alcohols using metal hydrides.
Aluminium hydride an overview sciencedirect topics. The most common metal hydrides are lithium aluminium hydride lialh 4 and sodium borohydride nabh 4 there are differences mechanistically in many cases the lithium cation is vital for reaction h h 2al h o r r li o r r h 2al h li o r h h 3al. Conjugate addition reactions university of nairobi. Curran and valerie wadyko for correcting the files according to the proposals of. No component of this product present at levels greater than or equal to 0. The ether solution of alane requires immediate use, because polymeric material rapidly precipitates as a solid. Lialh 4 is a source of the strongly basic hydride ion h. Identification of the substancemixture and of the companyundertaking. Environmental precautions should not be released into the. For example, it is used in the conversion of esters, carboxylic acids, acyl chlorides, aldehydes and ketones into their corresponding alcohols. Lithium aluminum hydride, pellets safety data sheet.
Lithium aluminum hydride is a strong reducing agent and water reactive substance. Pdf synthesis of lialh4 nanoparticles leading to a single. Do not attempt to take action without suitable protective equipment. Lithium and its compounds are possible teratogens by analogy to lithium carbonate which has equivocal human teratogenic data and positive animal teratogenic data. React violently on contact with many oxidizing agents. Sodium metal, potassium metal, lithium metal, lithium aluminum hydride separate from all aqueous solutions, and oxidizers. Lithium borohydride is commonly used for the selective reduction of esters and lactones to the corresponding alcohols in the presence of carboxylic acids, tertiary amides, and nitriles. Take precautionary measures against static discharges. Can anyone suggest the best method for lithium aluminium. Keep and store away from heatflame, oxidizers, acids, and moisturewater sources. The reactivity of lithium borohydride is dependent on the reaction medium and follows the order.
Lithium hydride is generally immediately available in most volumes. What are the groups that lialh4 can and cannot reduce. Accidental release measures personal precautions ensure adequate ventilation. Hydride nucleophiles lithium aluminium hydride lialh 4 copper hydride cuh 2. Lithium aluminum hydride is a powerful reducing agent. Potassium hydride, sodium hydride, lithium aluminum hydride, diethylaluminium hydride. The first is the formation aluminum alkyloxide complex. Lithium aluminium hydride reacts vigourously with water, acids and alcohols and can easily catch fire. It is usually supplied in the form of a fine grey powder.
Instead, slowly add lialh 4 to anhydrous solvent in the reaction flask. In addition, aldehydes, ketones, epoxides, alkyl halides, and many other. Can anyone suggest the best method for lithium aluminium hydride work up. For storing lah, keep sealed under an inert atmosphere.
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