chemistry

Sodium bis(2-methoxyethoxy)aluminium hydride

Sodium bis(2-methoxyethoxy)aluminium hydride is a chemistry topic covered in the lgStudy science library. This page brings together a partial reference excerpt, illustrations, worked examples, real-world applications and a short study plan, so you can understand Sodium bis(2-methoxyethoxy)aluminium hydride rather than just read about it. In short: Sodium bis(2-methoxyethoxy)aluminium hydride (SMEAH; trade names Red-Al, Synhydrid, Vitride) is a hydride reductant with the formula NaAlH2(OCH2CH2OCH3)2. It is also commonly known as SDMA (Sodium dihydrido-bis(2-methoxyethoxy)aluminate) in scientific literature and chemical catalogs.

Key takeaways

Sodium bis(2-methoxyethoxy)aluminium hydride belongs to chemistry; place it in that map before memorising details.
Learn the definition first, then one example that makes the definition concrete.
Connect Sodium bis(2-methoxyethoxy)aluminium hydride to a quantity you can measure, compute or draw — that is where exam questions come from.
Reproduce the core statement of Sodium bis(2-methoxyethoxy)aluminium hydride from memory before moving on to harder problems.

Reference excerpt

Sodium bis(2-methoxyethoxy)aluminium hydride (SMEAH; trade names Red-Al, Synhydrid, Vitride) is a hydride reductant with the formula NaAlH2(OCH2CH2OCH3)2. It is also commonly known as SDMA (Sodium dihydrido-bis(2-methoxyethoxy)aluminate) in scientific literature and chemical catalogs. The trade name Red-Al refers to its being a reducing aluminium compound. It is used predominantly as a reducing agent in organic synthesis. The compound features a tetrahedral aluminium center attached to two hydride and two alkoxide groups, the latter derived from 2-methoxyethanol. Commercial solutions are colorless/pale yellow and viscous. At low temperatures (below -60°C), the solution solidifies to a glassy pulverizable substance with no sharp melting point. SMEAH is a versatile hydride reducing agent. It readily converts epoxides, aldehydes, ketones, carboxylic acids, esters, acyl halides, and anhydrides to the corresponding alcohols. Nitrogen derivates such as amides, nitriles, imines, and most other organonitrogen compounds are reduced to the corresponding amines. Nitroarenes can be converted to azoxyarenes, azoarenes, or hydroazoarenes, depending on the reaction conditions. Some common functional group reductions using SMEAH can be found below:

Comparison with lithium aluminium hydride As a reagent, SMEAH is comparable with lithium aluminium hydride (LAH, LiAlH4). It is a safer alternative to LAH and related hydrides. SMEAH exhibits similar reducing effects, but does not have the inconvenient pyrophoric nature, short shelf-life, or limited solubility of LAH. Upon contact with air and moisture, SMEAH reacts exothermically but does not ignite, and tolerates temperatures up to 200°C. Under dry conditions it has unlimited shelf life. It is soluble in aromatic solvents, whereas LAH is only soluble in ethers. For example, a solution greater than 70 wt.% concentration in toluene is commercially available. The reagent can be modified to effect partial reductions. SMEAH in toluene under reflux has been used to reduce aliphatic p-toluenesulfonamides (TsNR2) to the corresponding free amines and is one of the few reagents that can carry out this challenging reduction in general settings. Notably, LiAlH4 does not reduce this functional group unless forcing conditions are used.

References

External links "Red-Al, Sodium bis(2-methoxyethoxy)aluminumhydride". Organic Chemistry. Colletto, Chiara; Tessier, Arnaud; Lebreton, Jacques (2025). "SDMA (Synhydrid, Red-Al, Vitride): A Chemoselective and Safe Solution for Reduction Reactions". Organic Process Research & Development. 29 (8): 1916–1967. doi:10.1021/acs.oprd.5c00114.

Illustrations

Worked examples

Example 1 — a first encounter with Sodium bis(2-methoxyethoxy)aluminium hydride

Start with the simplest possible case. Write down what Sodium bis(2-methoxyethoxy)aluminium hydride claims or describes in one sentence, then invent the smallest concrete situation in which that sentence is true. In chemistry, the smallest case is usually a single object, a single equation or a single measurement. Check that every symbol or term in your sentence has a meaning in that case.

Example 2 — changing one variable

Take the situation from Example 1 and change exactly one quantity: double it, halve it, or set it to zero. Predict what should happen to Sodium bis(2-methoxyethoxy)aluminium hydride before you calculate. Comparing your prediction with the result is the fastest way to find out whether you understand the idea or only the words.

Example 3 — an exam-style question

Typical questions about Sodium bis(2-methoxyethoxy)aluminium hydride ask you to (a) state it precisely, (b) apply it to given data, and (c) explain a limitation. Practise writing all three answers in under five minutes; the third part is what separates a full-mark answer from an average one.

Applications of Sodium bis(2-methoxyethoxy)aluminium hydride

In research: Sodium bis(2-methoxyethoxy)aluminium hydride appears in chemistry research whenever the underlying quantities have to be modelled precisely. Papers usually cite it as a starting assumption and then explore where it breaks down.
In technology and industry: Engineering practice reuses Sodium bis(2-methoxyethoxy)aluminium hydride in design rules, simulations and safety margins. Knowing the idea lets you read a specification sheet and understand why the numbers look the way they do.
In the classroom: Sodium bis(2-methoxyethoxy)aluminium hydride is common in secondary-school and first-year university syllabi. It links to neighbouring topics Alkoxides, Aluminium complexes, Hydrido complexes, so understanding it makes those chapters shorter.
In everyday life: Look for Sodium bis(2-methoxyethoxy)aluminium hydride outside the textbook — in sport, cooking, traffic, electronics or the sky above you. An example you found yourself is remembered far longer than one you were given.

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How to study Sodium bis(2-methoxyethoxy)aluminium hydride in 20 minutes

Read the reference excerpt below once, without taking notes.
Close the page and write down what Sodium bis(2-methoxyethoxy)aluminium hydride means in your own words.
Compare your version with the excerpt and mark what you missed.
Work through the three examples above with pen and paper.
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Frequently asked questions

What is Sodium bis(2-methoxyethoxy)aluminium hydride in simple terms?

Why does Sodium bis(2-methoxyethoxy)aluminium hydride matter?

Because it connects several chemistry ideas at once: it gives you a definition you can apply, a quantity you can calculate, and a way to check whether a result is plausible.

How should I study Sodium bis(2-methoxyethoxy)aluminium hydride?

Read the excerpt, restate it from memory, then work through the examples and applications listed on this page. The five-step study plan above takes about twenty minutes.

What does this page cover?

It gives you a compact reference excerpt plus original lgStudy explanations, examples, applications and study material on Sodium bis(2-methoxyethoxy)aluminium hydride.