2-(Trimethylsilyl)ethoxymethyl chloride

Identifiers

CAS Number

* 76513-69-4 Y

3D model (JSmol)

* Interactive image

ChemSpider |

* 2006421

EC Number |

* 278-483-4

PubChem CID

* 2724271

InChI

* InChI=1S/C6H15ClOSi/c1-9(2,3)5-4-8-6-7/h4-6H2,1-3H3

Key: BPXKZEMBEZGUAH-UHFFFAOYSA-N

SMILES

* C[Si](C)(C)CCOCCl

Properties

Chemical formula

| 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 |
GHS Signal word | Danger

GHS hazard statements

| H226, H314

GHS precautionary statements

| 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):

* SizeSet

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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*[CID]: Compound ID
*[H226]: Flammable liquid and vapour
*[H314]: Causes severe skin burns and eye damage
*[P210]: Keep away from heat/sparks/open flames/hot surfaces – No smoking
*[P233]: Keep container tightly closed
*[P240]: Ground/bond container and receiving equipment
*[P241]: Use explosion-proof electrical/ventilating/light/…/equipment
*[P242]: Use only non-sparking tools
*[P243]: Take precautionary measures against static discharge
*[P260]: Do not breathe dust/fume/gas/mist/vapours/spray
*[P264]: Wash … thoroughly after handling
*[P280]: Wear protective gloves/protective clothing/eye protection/face protection
*[P301+330+331]: IF SWALLOWED: Rinse mouth. Do NOT induce vomiting
*[P303+361+353]: IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower
*[P304+340]: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
*[P305+351+338]: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do – continue rinsing
*[P310]: Immediately call a POISON CENTER or doctor/physician
*[P321]: Specific treatment (see … on this label)
*[P363]: Wash contaminated clothing before reuse
*[P370+378]: In case of fire: Use … for extinction
*[P403+235]: Store in a well ventilated place. Keep cool
*[P405]: Store locked up
*[P501]: Dispose of contents/container to …