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22722-98-1 - Sodium bis(2-methoxyethoxy)aluminum hydride, 70% w/w in toluene. - Sodium dihydrobis(2-methoxyethoxy)aluminate - A13292 - Alfa Aesar

A13292 Sodium bis(2-methoxyethoxy)aluminum hydride, 70% w/w in toluene.

CAS Number
22722-98-1
Synonyms
Sodium dihydrobis(2-methoxyethoxy)aluminate

Size Price ($) Quantity Availability
50g 27.50
250g 50.57
1000g 141.07
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Sodium bis(2-methoxyethoxy)aluminum hydride, 70% w/w in toluene.

MDL
MFCD00011631
EINECS
245-178-2

Chemical Properties

Formula
C6H16AlNaO4
Formula Weight
202.16
Flash Point
4°(39°F)
Density
1.020
Sensitivity
Moisture Sensitive
Solubility
Miscible with aromatic hydrocarbons, ether, tetrahydrofuran, dimethyl ether and dimethylformamide. Immiscible with aliphatic hydrocarbons.

Applications

Sodium bis(2-methoxyethoxy)aluminum hydride acts as a reducing agent in organic synthesis. It is used to prepare azoxyarenes, azoarenes and hydroazoarenes from nitroarenes. It plays an important role for the conversion of aldehydes, ketones, carboxylic acids, esters, acyl halides and anhydrides to primary alcohols. It is also employed in hydroaluminate alkenes and alkynes. It is utilized in the reduction of lactones and epoxides into diols. Further, it serves as a methylation reagent for aryl-activated compounds. In addition to this, it is involved in the reduction of amides, nitriles and amines to the corresponding amines.

Notes

Air and moisture sensitive. Keep the container tightly closed in a dry and well-ventilated place. Incompatible with water, oxidizing agents and combustible material.

Literature References

Convenient alternative to lithium aluminum hydride for many reductions: Coll. Czech. Chem. Commun., 34, 118 (1969). The reagent is more readily and safely handled, is more stable to air and can be used at high temperatures. For use in the stereospecific reduction of 2-yn-1-ols to (E)-allylic alcohols, and reviews, see: Org. Synth. Coll., 7, 524 (1990):

The reducing properties can be modified by addition of one mole of ethanol, which gives a reagent for the reduction of lactones to lactols, or one mole of N-methylpiperazine or morpholine, which gives a reagent for the high-yield reduction of esters to aldehydes: Synthesis, 526 (1976).

For use as a superior activator/initiator for the formation of Grignard reagents, see: Coll. Czech. Chem. Commun., 38, 1614 (1973).

Xu, J. B.; Cheng, K. J. Studies on the Alkaloids of the Calycanthaceae and Their Syntheses. Molecules 2015, 20 (4), 6715-6738.

Hatano, M.; Yamashita, K.; Mizuno, M.; Ito, O.; Ishihara, K. C-Selective and Diastereoselective Alkyl Addition to beta, gamma-Alkynyl-alpha-imino Esters with Zinc(II)ate Complexes. Angew. Chem. Int. Ed. 2015, 127 (9), 2745-2749.

GHS Hazard and Precautionary Statements

Hazard Statements: H225-H260-H304-H361-H373-H314-H332-H336

Highly flammable liquid and vapour. In contact with water releases flammable gases which may ignite spontaneously. May be fatal if swallowed and enters airways. Suspected of damaging fertility or the unborn child. May cause damage to organs through prolonged or repeated exposure. Causes severe skin burns and eye damage. Harmful if inhaled. May cause drowsiness or dizziness.

Precautionary Statements: P210-P231+P232-P260-P201-P301+P310-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Handle under inert gas. Protect from moisture. Do not breathe dust/fume/gas/mist/vapours/spray. Obtain special instructions before use. IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Rinse mouth. Do NOT induce vomiting. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Merck
14,8565
Hazard Class
4.3
Packing Group
I
Harmonized Tariff Code
2909.49
TSCA
Yes

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