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196193

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
NACRES:
NA.22
PubChem Substance ID:
24851740
UNSPSC Code:
12352000
MDL number:
MFCD00011631
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vapor pressure

21 mmHg ( 20 °C)

Quality Segment

200

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

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

target_organs

Central nervous system

supp_hazards

EUH014

Storage Class

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

wgk

WGK 3

flash_point_f

39.2 °F - closed cup

flash_point_c

4 °C - closed cup

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

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