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92749

Sigma-Aldrich

2-(Trimethylsilyl)ethoxymethyl chloride

≥95.0% (GC)

Synonym(s):

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

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About This Item

Linear Formula:
(CH3)3SiCH2CH2OCH2Cl
CAS Number:
Molecular Weight:
166.72
Beilstein:
3587289
EC Number:
MDL number:
UNSPSC Code:
12352101
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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

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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

Signal Word

Danger

Hazard Statements

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’.

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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.
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)
D. Crich et al.
Synlett, 117-117 (1990)
B.H. Lipshutz et al.
Tetrahedron Letters, 30, 7149-7149 (1989)

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