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HomeProduct name list2-(Trimethylsilyl)ethanol

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
2-(Trimethylsilyl)ethanol Structural

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).

2916-68-9 synthesis

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  n20/D 1.423(lit.)
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)
ghs
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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