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Sigma-Aldrich

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

≥60 wt. % in toluene

Synonyme(s) :

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

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50 G
48,10 €
500 G
97,40 €
250 G
110,00 €

About This Item

Formule linéaire :
NaAlH2(OCH2CH2OCH3)2
Numéro CAS:
Poids moléculaire :
202.16
Numéro MDL:
Code UNSPSC :
12352000
ID de substance PubChem :
Nomenclature NACRES :
NA.22

48,10 €


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Pression de vapeur

21 mmHg ( 20 °C)

Niveau de qualité

Limite d'explosivité

7 %

Pertinence de la réaction

reagent type: reductant

Concentration

≥60 wt. % in toluene

Densité

1.036 g/mL at 25 °C

Groupe fonctionnel

ether

Chaîne SMILES 

[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;;

Clé InChI

XJIQVZMZXHEYOY-UHFFFAOYSA-N

Description générale

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]

Informations légales

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

Mention d'avertissement

Danger

Classification des risques

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

Organes cibles

Central nervous system

Risques supp

Code de la classe de stockage

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

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

39.2 °F - closed cup

Point d'éclair (°C)

4 °C - closed cup


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Certificats d'analyse (COA)

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Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.

Consulter la Bibliothèque de documents

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)
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)
Efficient and stereodivergent synthesis of deoxyimino sugars
Hong B-C, et al.
Carbohydrate Research, 340(16), 2457-2468 (2005)
Properties of sodium bis-(2-methoxyethoxy) aluminium hydride. IV. Reduction of oximes, amides, lactams, imides and nitriles
v Cerny M, et al.
Collection of Czechoslovak Chemical Communications, 34(3), 1033-1041 (1969)

Articles

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

Questions

1–2 of 2 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/449/386/product-dating-information-mk.pdf

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  2. 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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