Skip to Content
Merck
All Photos(1)

Documents

92749

Sigma-Aldrich

2-(Trimethylsilyl)ethoxymethyl chloride

≥95.0% (GC)

Synonym(s):

(2-Chloromethoxyethyl)trimethylsilane, Chloromethyl 2-trimethylsilylethyl ether, SEM-Cl, SEM-chloride

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Linear Formula:
(CH3)3SiCH2CH2OCH2Cl
CAS Number:
76513-69-4
Molecular Weight:
166.72
Beilstein:
3587289
EC Number:
278-483-4
MDL number:
MFCD00009919
UNSPSC Code:
12352101
PubChem Substance ID:
57653488
NACRES:
NA.22

Assay

≥95.0% (GC)

form

liquid

refractive index

n20/D 1.435 (lit.)
n20/D 1.436

bp

170-172 °C (lit.)
57-59 °C/8 mmHg (lit.)

density

0.942 g/mL at 25 °C (lit.)

shipped in

wet ice

storage temp.

−20°C

SMILES string

C[Si](C)(C)CCOCCl

InChI

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

InChI key

BPXKZEMBEZGUAH-UHFFFAOYSA-N

Looking for similar products? Visit Product Comparison Guide

Related Categories

General description

2-(Trimethylsilyl)ethoxymethyl chloride (SEM-Cl) is a widely used reagent for the preparation protection groups for amines, alcohols, phenols, and carboxy groups. The nitrogen of amides and sulfonamides groups are also protected by using SEM-Cl reagent.

Application

SEM-Cl can be used as a reagent for the preparation of 2,4,5-trisubstituted tetrahydropyrans form homoallylic alcohols by a Prins-type cyclization reaction. It can also be used in the synthesis of amino acid SEM esters from N-protected amino acids in the presence of lithium carbonate.

Other Notes

Protecting-group reagent for alcohols and other functional groups selectively removable with Bu4NF ; Protecting group for pyrroles and imidazoles, facilitating selective metalation ; Reagent for the introduction of a protected C1 building block

Pictograms

FlameCorrosion
GHS02,GHS05

Signal Word

Danger

Hazard Statements

H226,H314

Hazard Classifications

Flam. Liq. 3 - Skin Corr. 1B

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

114.8 °F - closed cup

Flash Point(C)

46 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

B.H. Lipshutz et al.
Tetrahedron Letters, 21, 3343-3343 (1980)
Mild, selective cleavage of amino acid and peptide ?-(trimethylsilyl) ethoxymethyl (SEM) esters by magnesium bromide.
Chen W, et al.
Tetrahedron Letters, 38(23), 4025-4028 (1997)
T. Wada et al.
Tetrahedron Letters, 36, 1683-1683 (1995)
Protecting groups for the pyrrole and indole nitrogen atom. The [2-(trimethylsilyl) ethoxy] methyl moiety. Lithiation of 1-[[2-(trimethylsilyl) ethoxy] methyl] pyrrole.
Muchowski J, et al.
The Journal of Organic Chemistry, 49(1), 203-205 (1984)
K Kim et al.
Chemical communications (Cambridge, England), (21), 2268-2269 (2002-09-21)
A synthetic method to prepare a novel polymer-supported 2-(diphenylmethylsilyl)ethoxymethyl chloride (DSEM-Cl) linker and its applications are described.
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service