Sodium bis(2-methoxyethoxy)aluminiumhydride
Synonym(s):SBAH;Sodium bis(2-methoxyethoxy)aluminum dihydride;Sodium dihydrido-bis(2-methoxyethoxy)aluminate
- CAS NO.:22722-98-1
- Empirical Formula: C6H16AlNaO4
- Molecular Weight: 202.16
- MDL number: MFCD00011631
- EINECS: 245-178-2
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-12-18 14:08:52
What is Sodium bis(2-methoxyethoxy)aluminiumhydride?
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.
The Uses of Sodium bis(2-methoxyethoxy)aluminiumhydride
Reducing agent.
The Uses of Sodium bis(2-methoxyethoxy)aluminiumhydride
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.
The Uses of Sodium bis(2-methoxyethoxy)aluminiumhydride
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.
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.
It is also used as a catalyst in the ring-opening polymerization reactions.
Properties of Sodium bis(2-methoxyethoxy)aluminiumhydride
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 |
color | Clear to slightly hazy, colorless to light amber |
Specific Gravity | 1.036 |
explosive limit | 7% |
Water Solubility | reacts |
Hydrolytic Sensitivity | 8: reacts rapidly with moisture, water, protic solvents |
Sensitive | Air & Moisture Sensitive |
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) |
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 information for Sodium bis(2-methoxyethoxy)aluminiumhydride
Signal word | Danger |
Pictogram(s) |
Flame Flammables GHS02 Corrosion Corrosives GHS05 Exclamation Mark Irritant GHS07 Health Hazard GHS08 |
GHS Hazard Statements |
H225:Flammable liquids H260:Substances And Mixtures Which, In Contact With Water,Emit Flammable Gases H304:Aspiration hazard H314:Skin corrosion/irritation H336:Specific target organ toxicity,single exposure; Narcotic effects H373:Specific target organ toxicity, repeated exposure H412:Hazardous to the aquatic environment, long-term hazard |
Precautionary Statement Codes |
P210:Keep away from heat/sparks/open flames/hot surfaces. — No smoking. P280:Wear protective gloves/protective clothing/eye protection/face protection. P231+P232:Handle under inert gas. Protect from moisture. P301+P330+P331:IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. P303+P361+P353:IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
Computed Descriptors for Sodium bis(2-methoxyethoxy)aluminiumhydride
InChIKey | OKUDBXZACZBZJE-UHFFFAOYSA-N |
Sodium bis(2-methoxyethoxy)aluminiumhydride manufacturer
Bondbay Pharmaceuticals Pvt Ltd
Anand Agencies
ASM Organics
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