![]() | |
Identifiers | |
---|---|
3D model (
JSmol)
|
|
ChemSpider | |
ECHA InfoCard | 100.071.328 |
EC Number |
|
PubChem
CID
|
|
CompTox Dashboard (
EPA)
|
|
| |
| |
Properties | |
C6H15ClOSi | |
Molar mass | 166.72 g·mol−1 |
Appearance | Colorless liquid [1] |
Boiling point | 57–59 °C (330–332 K) (8 mmHg) [1] |
Hazards | |
GHS labelling: | |
![]() ![]() | |
Danger | |
H226, H314 | |
P210, P233, P240, P241, P242, P243, P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P370+P378, P403+P235, P405, P501 | |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
2-(Trimethylsilyl)ethoxymethyl chloride (SEM-Cl) is an organochlorine compound with the formula C6H15ClOSi, which was developed by Bruce H. Lipshutz during his work on the synthesis of N-methylmaysenine. It is used to protect hydroxyl groups, which can be cleaved with fluoride in organic solvents selectively under mild conditions. [1] Typically tetrabutylammonium fluoride and caesium fluoride can be used as deprotection reagents. Alternatives such as magnesium bromide, [2] lithium tetrafluoroborate and boron trifluoride etherate were also developed to deprotect SEM group. [3]