Sodium bis(2-methoxyethoxy)aluminiumhydride Property

Boiling point:

396-402°C

Density 

1.036 g/mL at 25 °C

vapor pressure 

21 mm Hg ( 20 °C)

Flash point:

40 °F

storage temp. 

Flammables area

solubility 

Miscible with aromatic hydrocarbons, ether, tetrahydrofuran, dimethyl ether and dimethylformamide. Immiscible with aliphatic hydrocarbons.

form 

Viscous Liquid

Specific Gravity

1.036

color 

Clear to slightly hazy, colorless to light amber

explosive limit

7%

Water Solubility 

reacts

Sensitive 

Air & Moisture Sensitive

Hydrolytic Sensitivity

8: reacts rapidly with moisture, water, protic solvents

Merck 

14,8564

Exposure limits

ACGIH: TWA 20 ppm
OSHA: Ceiling 300 ppm; TWA 200 ppm
NIOSH: IDLH 500 ppm; TWA 100 ppm(375 mg/m3); STEL 150 ppm(560 mg/m3)

InChIKey

OKUDBXZACZBZJE-UHFFFAOYSA-N

LogP

-2.64 at 25℃ and pH7

CAS DataBase Reference

22722-98-1(CAS DataBase Reference)

EPA Substance Registry System

Aluminate(1-), dihydrobis[2-(methoxy-.kappa.O)ethanolato-.kappa.O]-, sodium (22722-98-1)

Safety

Hazard Codes 

F,C

Risk Statements 

11-14/15-34-48/20-63-65-67

Safety Statements 

26-36/37/39-43-45-62-46-16-9

RIDADR 

UN 3399 4.3/PG 1

WGK Germany 

2

F 

1-10

TSCA 

Yes

HazardClass 

4.3

PackingGroup 

I

HS Code 

29319090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H225Highly Flammable liquid and vapour

H260In contact with water releases flammable gases which may ignite spontaneously

H304May be fatal if swallowed and enters airways

H314Causes severe skin burns and eye damage

H336May cause drowsiness or dizziness

H373May cause damage to organs through prolonged or repeated exposure

H412Harmful to aquatic life with long lasting effects

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P231+P232Handle under inert gas. Protect from moisture.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P330+P331IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Sodium bis(2-methoxyethoxy)aluminiumhydride Chemical Properties,Usage,Production

Chemical Properties

Sodium [bis(2-methoxyethoxy)]dihydridoaluminate (SDMA), NaAlH2(OCH2CH2OCH3)2, is a colorless, viscous liquid at room temperature that solidifies to a glass below 0 C; there is no sharp melting point. It is stable up to 170 C and decomposes above 214 C. At higher temperature decomposition is sudden and spontaneous. The presence of the two methoxyethoxy groups confers solubility not only in ethers but also in aromatic hydrocarbons. It is completely miscible with toluene at concentrations below 6 % and above 42 %. Viscous solutions of SDMA can be handled in contact with air, although atmospheric moisture causes hydrolysis.

Uses

Sodium bis(2-methoxyethoxy)aluminum hydride acts as a reducing agent in organic synthesis. It is used to prepare azoxyarenes, azoarenes and hydroazoarenes from nitroarenes. It plays an important role for the conversion of aldehydes, ketones, carboxylic acids, esters, acyl halides and anhydrides to primary alcohols. It is also employed in hydroaluminate alkenes and alkynes. It is utilized in the reduction of lactones and epoxides into diols. Further, it serves as a methylation reagent for aryl-activated compounds. In addition to this, it is involved in the reduction of amides, nitriles and amines to the corresponding amines.

Uses

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.

Uses

Reducing agent.

Preparation

One method of preparation is the controlled alcoholysis of NaAlH4 with 2- methoxyethanol:
NaAlH4+2 CH3OCH2CH2OH→NaAlH2(OCH2CH2OCH3)2 +H2
On an industrial scale, however, it is produced by direct synthesis from sodium, aluminum, and 2-methoxyethanol at 140 – 155 C in an atmosphere of hydrogen at at least 7 MPa:
Na+Al+2 CH3OCH2CH2OH→NaAlH2(OCH2CH2OCH3)2
The quantity of hydrogen required is generated in situ by the reaction of sodium and aluminum with the alcohol. SDMA(Sodium bis(2-methoxyethoxy)aluminiumhydride) is marketed as a 70 % solution in toluene (r = 1.036 g/cm3 ) under the name Vitride (Hexcel).

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.