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196193

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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$55.10
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$142.00

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About This Item

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

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vapor pressure

21 mmHg ( 20 °C)

Quality Level

expl. lim.

7 %

reaction suitability

reagent type: reductant

concentration

≥60 wt. % in toluene

density

1.036 g/mL at 25 °C

functional group

ether

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

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This Item
214973190306192724
Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

reaction suitability

reagent type: reductant

reaction suitability

reagent type: reductant

reaction suitability

reagent type: reductant

reaction suitability

reagent type: reductant

density

1.036 g/mL at 25 °C

density

1.23 g/mL at 25 °C

density

0.701 g/mL at 25 °C

density

0.846 g/mL at 25 °C

vapor pressure

21 mmHg ( 20 °C)

vapor pressure

-

vapor pressure

-

vapor pressure

-

expl. lim.

7 %

expl. lim.

-

expl. lim.

-

expl. lim.

-

concentration

≥60 wt. % in toluene

concentration

1.0 M in methylene chloride

concentration

1.0 M in hexanes

concentration

25 wt. % in toluene

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.[1][2][3]

SBAH is a reducing agent used to reduce functional groups like carbonyls, amides, epoxides, esters, and carboxylic acids.[4]

Application

Employed in the efficient reduction of N-Boc amino acid secondary amides leading to chiral diamines.[5]
Red-Al® sodium bis(2-methoxyethoxy)aluminum hydride can be used as:       
  • A tosyl deprotecting agent.[6]       
  • A catalyst for crosslinking of polyvinylsilanes (PVS) by Si-Si dehydrocoupling reaction in the presence of group 4 metallocene complexes.[7]       
  • A reducing reagent for the synthesis of optically active N-protected amino alcohols and peptide alcohols.[8]

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

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


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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)
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)
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)
Living ring-opening polymerization of L-lactide catalyzed by red-Al
Li Hong, et al.
Organometallics, 23(6), 1411-1415 (2004)

Articles

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

Questions

1–3 of 3 Questions  
  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/418/501/product-dating-information-06-25-mk.pdf

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  2. We are looking to use this as a hydrogen generation system in a closed system to fill a balloon. What volume of gas is generated per kg of solid product.

    1 answer
    1. The theoretical yield from 1 kilogram of this product is 110 Liters of hydrogen gas. The actual yield would likely be some amount less than the theoretical yield.

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  3. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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