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Sigma-Aldrich

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

≥60 wt. % in toluene

Sinónimos:

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

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About This Item

Fórmula lineal:
NaAlH2(OCH2CH2OCH3)2
Número de CAS:
22722-98-1
Peso molecular:
202.16
Número MDL:
MFCD00011631
Código UNSPSC:
12352000
ID de la sustancia en PubChem:
24851740
NACRES:
NA.22
En este momento no podemos mostrarle ni los precios ni la disponibilidad

presión de vapor

21 mmHg ( 20 °C)

Nivel de calidad

200

lim. expl.

7 %

idoneidad de la reacción

reagent type: reductant

concentración

≥60 wt. % in toluene

densidad

1.036 g/mL at 25 °C

grupo funcional

ether

cadena 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;;

Clave InChI

XJIQVZMZXHEYOY-UHFFFAOYSA-N

Categorías relacionadas

Descripción general

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]

Aplicación

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]

Información legal

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

Palabra de señalización

Danger

Clasificaciones de peligro

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

Órganos de actuación

Central nervous system

Riesgos supl.

EUH014

Código de clase de almacenamiento

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

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

39.2 °F - closed cup

Punto de inflamabilidad (°C)

4 °C - closed cup

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Certificados de análisis (COA)

Lot/Batch Number
SDBB2249
SHBR8939
SHBR3238
STBK7335
SHBP7938

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Visite la Librería de documentos

Tetrahedron, 47, 2773-2773 (1991)
A Viewpoint on Chemical Reductions of Carbon--Oxygen Bonds in Renewable Feedstocks Including CO2 and Biomass
Chauvier C and Cantat T
ACS Catalysis, 7(3), 2107-2115 (2017)
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)
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
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Artículos

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.

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

      Helpful?

  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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