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2-(Trimethylsilyl)ethoxymethyl chloride

Topic: Chemistry

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2-(Trimethylsilyl)ethoxymethyl chloride
Identifiers
3D model (JSmol)
ChemSpider
EC Number
  • 278-483-4
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 pictograms GHS02: FlammableGHS05: Corrosive
GHS Signal word Danger
H226, H314
P210, P233, P240, P241, P242, P243, P260, P264, P280, P301+330+331, P303+361+353, P304+340, P305+351+338, P310, P321, P363, P370+378, P403+235, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Tracking categories (test):

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]

References

  1. ↑ 1.0 1.1 1.2 Lipshutz, Bruce H.; Pegram, Joseph J. (1980). "β-(Trimethylsilyl)ethoxymethyl chloride. A new reagent for the protection of the hydroxyl group". Tetrahedron Letters (Elsevier BV) 21 (35): 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 (American Chemical Society (ACS)) 2 (10): 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. https://books.google.com/books?id=0RQEsfYCuBcC&pg=PA176. 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 (American Chemical Society (ACS)) 20 (7): 1370–1376. doi:10.1021/acs.oprd.6b00128. ISSN 1083-6160. 



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