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

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

Stock No. Size Price ($) Quantity Availability
A13292-18 50g 28.50
A13292-30 250g 52.60
A13292-0B 1000g 161.00
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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
Storage & Sensitivity
Moisture Sensitive. Ambient temperatures.
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-H304-H314-H318-H361-H373-X

Highly flammable liquid and vapour. May be fatal if swallowed and enters airways. Causes severe skin burns and eye damage. Causes serious eye damage. Suspected of damaging fertility or the unborn child. May cause damage to organs through prolonged or repeated exposure.

Precautionary Statements: P201-P202-P210-P233-P240-P241-P242-P243-P261-P262-P264b-P271-P280-P301+P310-P303+P361+P353-P304+P340-P305+P351+P338-P310-P312-P330-P331-P363-P372-P374-P380-P501c

Obtain special instructions before use. Do not handle until all safety precautions have been read and understood. Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Keep container tightly closed. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. Use only non-sparking tools. Take precautionary measures against static discharge. Avoid breathing dust/fume/gas/mist/vapours/spray. Do not get in eyes, on skin, or on clothing. Wash face, hands and any exposed skin thoroughly after handling Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. 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 INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Call a POISON CENTER or doctor/physician if you feel unwell. Rinse mouth. Do NOT induce vomiting. Wash contaminated clothing before reuse. Explosion risk in case of fire. Fight fire with normal precautions from a reasonable distance. Evacuate area. Dispose of contents/ container to an approved waste disposal plant

Other References

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

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