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Sigma-Aldrich

Red-Al® sodium bis(2-methoxyethoxy)aluminum hydride solution

≥60 wt. % in toluene

Synonym(s):

SBAH, Sodium bis(2-methoxyethoxy)aluminum dihydride, Sodium dihydrido-bis(2-methoxyethoxy)aluminate

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About This Item

Linear Formula:
NaAlH2(OCH2CH2OCH3)2
CAS Number:
22722-98-1
Molecular Weight:
202.16
MDL number:
MFCD00011631
UNSPSC Code:
12352000
PubChem Substance ID:
24851740
NACRES:
NA.22

vapor pressure

21 mmHg ( 20 °C)

Quality Level

200

expl. lim.

7 %

reaction suitability

reagent type: reductant

concentration

≥60 wt. % in toluene

density

1.036 g/mL at 25 °C

SMILES string

[Na+].[H][Al-]([H])(OCCOC)OCCOC

InChI

1S/2C3H7O2.Al.Na.2H/c2*1-5-3-2-4;;;;/h2*2-3H2,1H3;;;;/q2*-1;2*+1;;

InChI key

XJIQVZMZXHEYOY-UHFFFAOYSA-N

General description

Red-Al® sodium bis(2-methoxyethoxy)aluminum hydride [NaAlH2(OCH2CH2OCH3)2] is used as a versatile reducing agent in organic synthesis. It is used to reduce:

  • Aldehydes, ketones, esters, and anhydrides to primary alcohols.
  • Ketoximes and aldoximes to primary amines.
  • Cyclic compounds such as lactones and epoxides to diols.


It is also used as a catalyst in the ring-opening polymerization reactions.

SBAH is a reducing agent used to reduce functional groups like carbonyls, amides, epoxides, esters, and carboxylic acids.

Application

Employed in the efficient reduction of N-Boc amino acid secondary amides leading to chiral diamines.
Red-Al® sodium bis(2-methoxyethoxy)aluminum hydride can be used as:       
  • A tosyl deprotecting agent.       
  • A catalyst for crosslinking of polyvinylsilanes (PVS) by Si-Si dehydrocoupling reaction in the presence of group 4 metallocene complexes.       
  • A reducing reagent for the synthesis of optically active N-protected amino alcohols and peptide alcohols.

Legal Information

Red-Al is a registered trademark of Merck KGaA, Darmstadt, Germany

signalword

Danger

Hazard Classifications

Aquatic Chronic 3 - Asp. Tox. 1 - Eye Dam. 1 - Flam. Liq. 2 - Repr. 2 - Skin Corr. 1B - STOT RE 2 Inhalation - STOT SE 3 - Water-react 1

target_organs

Central nervous system

supp_hazards

EUH014

Storage Class

4.3 - Hazardous materials which set free flammable gases upon contact with water

wgk_germany

WGK 3

flash_point_f

39.2 °F - closed cup

flash_point_c

4 °C - closed cup

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Reductive cleavage of sulfonamides with sodium bis (2-methoxyethoxy) aluminum hydride
Gold EH and Babad E
The Journal of Organic Chemistry, 37(13), 2208-2210 (1972)
Living ring-opening polymerization of L-lactide catalyzed by red-Al
Li Hong, et al.
Organometallics, 23(6), 1411-1415 (2004)
Alexandra J Townsend et al.
Biochimica et biophysica acta. Bioenergetics, 1859(9), 666-675 (2018-03-20)
Non-photochemical quenching (NPQ) of chlorophyll fluorescence is the process by which excess light energy is harmlessly dissipated within the photosynthetic membrane. The fastest component of NPQ, known as energy-dependent quenching (qE), occurs within minutes, but the site and mechanism of
Tetrahedron Letters, 47, 1717-1717 (2006)
Simple and efficient synthesis of chiral amino alcohols with an amino acid-based skeleton
Juszczyk P, et al.
Lett. Pept. Sci., 10(2), 79-82 (2003)
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Articles

Red-Al® Reducing Agent

Red-Al® is a versatile and safe reducing agent, serving as a substitute for LiAlH4 in many reactions, with nonpyrophoric properties.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

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