|
|
| | Sodium bis(2-methoxyethoxy)aluminiumhydride Basic information |
| | Sodium bis(2-methoxyethoxy)aluminiumhydride Chemical Properties |
| Boiling point | 396-402°C | | density | 1.036 g/mL at 25 °C | | vapor pressure | 21 mm Hg ( 20 °C) | | Fp | 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) |
| | Sodium bis(2-methoxyethoxy)aluminiumhydride Usage And Synthesis |
| 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 | Reducing agent. | | 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.
| | 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. | | reaction suitability | reagent type: reductant |
| | Sodium bis(2-methoxyethoxy)aluminiumhydride Preparation Products And Raw materials |
|