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
• Linear Formula: NaAlH₂(OCH₂CH₂OCH₃)₂
• CAS Number: 22722-98-1
• Molecular Weight: 202.16
• MDL number: MFCD00011631
• UNSPSC Code: 12352000
• PubChem Substance ID: 24851740
• NACRES: NA.22

Properties

• vapor pressure: 21 mmHg ( 20 °C)
• Quality Level: 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

Description

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

Safety Information

• Pictograms: GHS02,GHS08,GHS05,GHS07
• Signal Word: Danger
• Hazard Statements: H225,H260,H304,H314,H336,H361d,H373,H412
• Precautionary Statements: P210 - P231 + P232 - P280 - P301 + P330 + P331 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338
• 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
• Supplementary Hazards: EUH014
• Storage Class Code: 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