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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.
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.
Hazard Statements: H226-H315-H319-H335
Flammable liquid and vapour. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: P210-P233-P235-P240-P241-P242-P243-P261-P264b-P271-P280-P303+P361+P353-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P363-P370+P378q-P501c
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Keep container tightly closed. Keep cool. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. Use only non-sparking tools. Take precautionary measures against static discharge. Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Call a POISON CENTER or doctor/physician if you feel unwell. If skin irritation occurs: Get medical advice/attention. If eye irritation persists: Wash contaminated clothing before reuse. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant