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2916-68-9 - 2-(Trimethylsilyl)ethanol, 98+% - 2-Hydroxyethyltrimethylsilane - B20970 - Alfa Aesar

B20970 2-(Trimethylsilyl)ethanol, 98+%

CAS Number
2916-68-9
Synonyms
2-Hydroxyethyltrimethylsilane

Size Price ($) Quantity Availability
5g 72.10
25g 245.14
100g 771.47
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2-(Trimethylsilyl)ethanol, 98+%

MDL
MFCD00002825
EINECS
220-844-5

Chemical Properties

Formula
(CH3)3SiCH2CH2OH
Formula Weight
118.25
Boiling Point
71-72°/10mm
Flash Point
50°(122°F)
Density
0.825
Refractive Index
1.4250
Solubility
Miscible with water.

Applications

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.

Notes

Keep away from sources of ignition. Keep container tightly closed in a dry and well-ventilated place.

Literature References

Carboxyl groups can be protected as 2-(trimethylsilyl)ethyl (TMSE) esters by carbodiimide coupling: Helv. Chim. Acta, 60, 2711 (1977); J. Org. Chem., 62, 93 (1997), from the acid chloride in pyridine: Helv. Chim. Acta, 60, 3039 (1977), or refluxing the acid in THF in the presence of TMS chloride: J. Am. Chem. Soc., 106, 3030 (1984). The TMSE protecting group is useful in peptide synthesis. Cleavage is readily effected with TBAF in DMF or DMSO: Helv. Chim. Acta, 60, 2711 (1977); Bioorg. Med. Chem. Lett., 3, 437 (1993).

Qu, H.; Sun, W.; Sun, T.; Sollogoub, M.; Zhang, Y. Synthesis and characterization of four novel 2-(trimethylsilyl)ethyl glycosides. Res. Chem. Intermed. 2015, 41 (2), 1107-1113.

Sano, S.; Sumiyoshi, H.; Handa, A.; Tokizane, R.; Nakao, M. A novel synthetic approach to glycerophospholipids via Horner-Wadsworth-Emmons reaction of mixed phosphonoacetate. Tetrahedron Lett. 2015, 56 (32), 4686-4688.

GHS Hazard and Precautionary Statements

Hazard Statements: H226-H315-H319-H335

Flammable liquid and vapour. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Precautionary Statements: P210-P261-P280-P240-P303+P361+P353-P305+P351+P338-P304+P340-P362-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. Ground/bond container and receiving equipment. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Take off contaminated clothing and wash before reuse. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Beilstein
1732034
Hazard Class
3
Packing Group
III
Harmonized Tariff Code
2931.90
TSCA
No
RTECS
KM5480000

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