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Sigma-Aldrich

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

≥60 wt. % in toluene

Sinonimo/i:

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

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About This Item

Formula condensata:
NaAlH2(OCH2CH2OCH3)2
Numero CAS:
Peso molecolare:
202.16
Numero MDL:
Codice UNSPSC:
12352000
ID PubChem:
NACRES:
NA.22

Tensione di vapore

21 mmHg ( 20 °C)

Livello qualitativo

Limite di esplosione

7 %

Impiego in reazioni chimiche

reagent type: reductant

Concentrazione

≥60 wt. % in toluene

Densità

1.036 g/mL at 25 °C

Gruppo funzionale

ether

Stringa SMILE

[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;;
XJIQVZMZXHEYOY-UHFFFAOYSA-N

Descrizione generale

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.

Applicazioni

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.

Note legali

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

Avvertenze

Danger

Classi di pericolo

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

Organi bersaglio

Central nervous system

Rischi supp

Codice della classe di stoccaggio

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

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

39.2 °F - closed cup

Punto d’infiammabilità (°C)

4 °C - closed cup


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I clienti hanno visto anche

Living ring-opening polymerization of L-lactide catalyzed by red-Al
Li Hong, et al.
Organometallics, 23(6), 1411-1415 (2004)
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
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)
Tetrahedron Letters, 47, 1717-1717 (2006)

Articoli

Red-Al®, or sodium bis(2-methoxyethoxy)aluminum dihydride (Vitride®, SMEAH), is a versatile reducing agent and a good substitute for LiAlH4 in many reactions. Red-Al® is nonpyrophoric, although still moisture-sensitive, and is available in solution, allowing for easier handling compared to LiAlH4.

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