sodium 2,5,7,10-tetraoxa-6-aluminaundecan-6-uide

• ChemBase ID: 123399
• Molecular Formular: C6H15AlNaO4
• Molecular Mass: 201.152208
• Monoisotopic Mass: 201.06834187
• SMILES: [AlH-](OCCOC)OCCOC.[Na+]
• Canonical SMILES: COCCO[AlH-]OCCOC.[Na+]
• InChI: InChI=1S/2C3H7O2.Al.Na/c2*1-5-3-2-4;;/h2*2-3H2,1H3;;/q2*-1;2*+1
• InChIKey: CKVKLEFDNAHFMO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium 2,5,7,10-tetraoxa-6-aluminaundecan-6-uide
• IUPAC Traditional name: sodium 2,5,7,10-tetraoxa-6-aluminaundecan-6-uide
• Synonyms: bis(2-methoxyethoxy)aluminum(III) sodium hydride; Synhydrid; Vitride; Red-Al; SBAH; Sodium bis(2-methoxyethoxy)aluminum dihydride; Sodium dihydrido-bis(2-methoxyethoxy)aluminate; Red-Al® sodium bis(2-methoxyethoxy)aluminum hydride solution; Sodium dihydrobis(2-methoxyethoxy)aluminate; Sodium bis(2-methoxyethoxy)aluminum hydride; 二氢双(2-甲氧乙氧基)铝酸钠; Red-Al® 双(2-甲氧乙氧基)氢化铝钠 溶液; 双(2-甲氧基乙氧基)氢化铝钠

Database IDs

• CAS Number: 22722-98-1
• EC Number: 245-178-2
• MDL Number: MFCD00011631
• Merck Index: 148565
• PubChem SID: 162217752; 24886202; 24851740
• PubChem CID: 16684438; 16689465
• Chemspider ID: 21169529
• Wikipedia Title: Red-Al

CALCULATED PROPERTIES

• Molar Refractivity: 37.7808 cm^3
• Polarizability: 17.50261 Å^3
• Polar Surface Area: 36.92 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true
• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 0.8518
• LogD (pH = 7.4): 0.8518
• Log P: 0.8518

PROPERTIES

Physical Property

• Apperance: Transparent crystals
• Flash Point: 39 °F; 39.2 °F; 4 °C; 4°C(39°F)
• Density: 1.02 g/mL at 20 °C; 1.020; 1.036 g/mL at 25 °C
• Vapor Pressure: 21 mmHg ( 20 °C)

Safety Information

• Storage Warning: Moisture Sensitive
• European Hazard Symbols: Corrosive (C); Flammable (F); X
• UN Number: 3399; UN3399
• German water hazard class: 2
• Hazard Class: 4.3
• Packing Group: 1; I
• Risk Statements: 11-14/15-34-48/20-63; 11-14/15-34-48/20-63-65-67; 63-11-14/15-34-48/20-65-67
• Safety Statements: 26-36/37/39-43.11-45-62; 7/8-9-16-20-23-26-30-33-36/37/39-43h-...; 9-16-26-36/37/39-43-45
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS05; GHS06; GHS07; GHS08
• GHS Signal Word: Danger
• Main Hazard: Unstable toward water
• Explode Limits: 7 %
• GHS Hazard statements: H224-H260-H314-H318-H361-H373-H336; H225-H260-H301 + H311-H304-H315-H318-H336-H361d-H373
• GHS Precautionary statements: P210-P223-P231 + P232-P261-P370 + P378-P422; P210-P231+P232-P303+P361+P353-P305+P351+P338-P405-P501A
• RID/ADR: UN 3399 4.3/PG 1
• Supplemental Hazard Statements: Reacts violently with water.

Product Information

• Purity: 70% w/w in toluene.
• Concentration: ~70% in toluene (~3.5 M); ≥60 wt. % in toluene
• Grade: technical
• Salt Data: Na+
• Linear Formula: NaAlH2(OCH2CH2OCH3)2

DETAILS

Sigma Aldrich - 196193

Application
Employed in the efficient reduction of N-Boc amino acid secondary amides leading to chiral diamines.1
Versatile reducing agent.
Packaging
50, 500 g in Sure/Seal™
Legal Information
Red-Al is a registered trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - 71495

Other Notes
Review1
Legal Information
Red-Al is a registered trademark of Sigma-Aldrich Co. LLC

REFERENCES

• For use as a superior activator/initiator for the formation of Grignard reagents, see: Coll. Czech. Chem. Commun., 38, 1614 (1973).
• Convenient alternative to lithium aluminum hydride for many reductions: Coll. Czech. Chem. Commun., 34, 118 (1969). The reagent is more readily and safely handled, is more stable to air and can be used at high temperatures. For use in the stereospecific reduction of 2-yn-1-ols to (E)-allylic alcohols, and reviews, see: Org. Synth. Coll., 7, 524 (1990):
  
• The reducing properties can be modified by addition of one mole of ethanol, which gives a reagent for the reduction of lactones to lactols, or one mole of N-methylpiperazine or morpholine, which gives a reagent for the high-yield reduction of esters to aldehydes: Synthesis, 526 (1976).