2-(Trimethylsilyl)ethanol
Synonym(s):(2-Hydroxyethyl)trimethylsilane
- CAS NO.:2916-68-9
- Empirical Formula: C5H14OSi
- Molecular Weight: 118.25
- MDL number: MFCD00002825
- EINECS: 220-844-5
- SAFETY DATA SHEET (SDS)
- Update Date: 2023-10-19 16:57:28
What is 2-(Trimethylsilyl)ethanol?
Chemical properties
CLEAR COLOURLESS LIQUID
Physical properties
bp 50–52 °C/10 mmHg, 71–73 °C/35 mmHg; d 0.825 g cm?3.
The Uses of 2-(Trimethylsilyl)ethanol
2-(Trimethylsilyl)ethanol is a protecting reagent for carboxyl, phosphoryl, hydroxyl, and amino groups. It participates in the reactions of Phenol and Acid Protection, Alcohol Protection, Hemiacetal Protection, Amine Protection, Enol Ether Synthesis, Carbohydrate Chemistry etc.
The Uses of 2-(Trimethylsilyl)ethanol
2-(Trimethylsilyl)ethanol is used as a protecting reagent for carboxyl, phosphoryl, hydroxyl and amino group in organic synthesis. It is used as a precursor to prepare trimethyl(2-phenoxyethyl)silanes by reacting with aromatic fluoride. It is also used in the synthesis of teoc-protected amines by using the corresponding isocyanates.
The Uses of 2-(Trimethylsilyl)ethanol
Used to synthesize Teoc-protected amines via alcoholysis of the corresponding isocyanates.
Preparation
Three methods of preparation have been reported: (a) from the treatment of ethyl bromoacetate with zinc followed by the reaction with chlorotrimethylsilane1 and subsequent reduction of the resultant ethyl trimethylsilylacetate with lithium aluminum hydride2,3 or borane¨Ctetrahydrofuran(eq 1); (b) from the hydroboration/oxidation or oxymercuration/demercuration of vinyltrimethylsilane (eq 2); and (c)most conveniently, by the reaction of the Grignard reagent formed from (chloromethyl)trimethylsilane with paraformaldehyde (eq 3).
Purification Methods
If the NMR spectrum is not clean, then dissolve the alcohol in Et2O, wash it with aqueous NH4Cl solution, dry (Na2SO4), evaporate and distil it. The 3,4-dinitrobenzoyl derivative has m 66o (from EtOH). [NMR: Speier et al. J Am Chem Soc 79 974 1957, Z Naturforsch 14b 137 1959, Beilstein 4 IV 3951.]
Properties of 2-(Trimethylsilyl)ethanol
Boiling point: | 71-73 °C35 mm Hg(lit.) |
Density | 0.825 g/mL at 25 °C(lit.) |
refractive index | n |
Flash point: | 123 °F |
storage temp. | Sealed in dry,2-8°C |
solubility | Chloroform (Slightly), Ethyl Acetate (Slightly) |
pka | 15.38±0.10(Predicted) |
form | Liquid |
color | Clear colorless |
Specific Gravity | 0.825 |
Water Solubility | soluble |
Hydrolytic Sensitivity | 4: no reaction with water under neutral conditions |
BRN | 1732034 |
Stability: | Hygroscopic |
CAS DataBase Reference | 2916-68-9(CAS DataBase Reference) |
NIST Chemistry Reference | Trimethyl-2-hydroxyethylsilane(2916-68-9) |
Safety information for 2-(Trimethylsilyl)ethanol
Signal word | Warning |
Pictogram(s) |
Flame Flammables GHS02 |
GHS Hazard Statements |
H226:Flammable liquids |
Precautionary Statement Codes |
P210:Keep away from heat/sparks/open flames/hot surfaces. — No smoking. |
Computed Descriptors for 2-(Trimethylsilyl)ethanol
InChIKey | ZNGINKJHQQQORD-UHFFFAOYSA-N |
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