2-(Trimethylsilyl)ethanol Chemical Properties

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

InChIKey

ZNGINKJHQQQORD-UHFFFAOYSA-N

CAS DataBase Reference

2916-68-9(CAS DataBase Reference)

NIST Chemistry Reference

Trimethyl-2-hydroxyethylsilane(2916-68-9)

Safety Information

Hazard Codes 

Xi,F

Risk Statements 

10-36/37/38

Safety Statements 

16-37/39-26-24/25

RIDADR 

UN 1987 3/PG 3

WGK Germany 

3

RTECS 

KM5480000

Hazard Note 

Flammable

TSCA 

No

HazardClass 

3

PackingGroup 

III

HS Code 

29310095

Toxicity

mouse,LD50,intraperitoneal,1122mg/kg (1122mg/kg),Doklady Akademii Nauk SSSR. Proceedings of the Academy of Sciences of the USSR. For English translation, see DBIOAM and DKBSAS. Vol. 229, Pg. 1011, 1976.

MSDS

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2-(Trimethylsilyl)ethanol Usage And Synthesis

Chemical Properties

CLEAR COLOURLESS LIQUID

Physical properties

bp 50–52 °C/10 mmHg, 71–73 °C/35 mmHg; d 0.825 g cm?3.

Uses

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.

Uses

Used to synthesize Teoc-protected amines via alcoholysis of the corresponding isocyanates.

Uses

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.

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.]

2-(Trimethylsilyl)ethanol(2916-68-9)Related Product Information

• TRIMETHYLSULFOXONIUM CHLORIDE
• N-(Trimethylsilyl)acetamide
• allyltrimethylammonium chloride
• Benzyltrimethylammonium chloride
• 2-Methoxyethanol
• Ethanol
• Vinyltrimethoxysilane
• Ethyl acetate
• Silicone rubber,methyl-vinyl
• 3-(TRIMETHYLSILYL)-1,2-PROPANEDIOL
• TERT-BUTYL TRIMETHYLSILYLACETATE
• FMOC-TYR(PO3(MDPSE)2)-OH
• (TRIMETHYLSILYL)ACETIC ACID
• 2-(Trimethylsilyl)ethoxymethyl chloride
• 2-(METHYLDIPHENYLSILYL)ETHANOL
• Ethyl (trimethylsilyl)acetate
• METHYL (TRIMETHYLSILYL)ACETATE
• 2-(TRIMETHYLSILYL)ETHOXYMETHYLTRIPHENYLPHOSPHONIUM CHLORIDE