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2-(Trimethylsilyl)ethoxymethyl chloride

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2-(Trimethylsilyl)ethoxymethyl chloride
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.071.328 Edit this at Wikidata
EC Number
  • 278-483-4
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C6H15ClOSi/c1-9(2,3)5-4-8-6-7/h4-6H2,1-3H3Key: BPXKZEMBEZGUAH-UHFFFAOYSA-N
SMILES
  • C(C)(C)CCOCCl
Properties
Chemical formula C6H15ClOSi
Molar mass 166.72 g·mol
Appearance Colorless liquid
Boiling point 57–59 °C (330–332 K) (8 mmHg)
Hazards
GHS labelling:
Pictograms GHS02: FlammableGHS05: Corrosive
Signal word Danger
Hazard statements H226, H314
Precautionary statements 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 , 100 kPa). Infobox references
Chemical compound

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. Typically tetrabutylammonium fluoride and caesium fluoride can be used as deprotection reagents. Alternatives such as magnesium bromide, lithium tetrafluoroborate and boron trifluoride etherate were also developed to deprotect SEM group.

References

  1. ^ Lipshutz, Bruce H.; Pegram, Joseph J. (1980). "β-(Trimethylsilyl)ethoxymethyl chloride. A new reagent for the protection of the hydroxyl group". Tetrahedron Letters. 21 (35). Elsevier BV: 3343–3346. doi:10.1016/s0040-4039(00)78684-9. ISSN 0040-4039.
  2. Vakalopoulos, Alexandros; Hoffmann, H. M. R. (2000-04-21). "Novel Deprotection of SEM Ethers: A Very Mild and Selective Method Using Magnesium Bromide". Organic Letters. 2 (10). American Chemical Society (ACS): 1447–1450. doi:10.1021/ol0057784. ISSN 1523-7060. PMID 10814469.
  3. Katritzky, A.R.; Kirby, G.W.; Meth-Cohn, O.; Rees, C.W. (1995). Comprehensive Organic Functional Group Transformations. Elsevier Science. p. 176. ISBN 978-0-08-042325-8. Retrieved 2021-10-25.

Further reading

  • Nair, Reji N.; Bannister, Thomas D. (2016-06-21). "Tale of Two Protecting Groups—Boc vs SEM—for Directed Lithiation and C–C Bond Formation on a Pyrrolopyridazinone Core". Organic Process Research & Development. 20 (7). American Chemical Society (ACS): 1370–1376. doi:10.1021/acs.oprd.6b00128. ISSN 1083-6160.
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