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92749

Sigma-Aldrich

2-(Trimethylsilyl)ethoxymethyl chloride

≥95.0% (GC)

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

Quality Level

100

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
GHS02,GHS05

Signal Word

Danger

Hazard Statements

H226,H314

Hazard Classifications

Flam. Liq. 3 - Skin Corr. 1B

WGK

WGK 3

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

危险化学品

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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D. Crich et al.
Synlett, 117-117 (1990)
B.H. Lipshutz et al.
Tetrahedron Letters, 30, 7149-7149 (1989)
N. Fujina et al.
Heterocycles, 34, 303-303 (1992)
2-(Trimethylsilyl) ethoxymethyl Chloride
Earley J and Adams CM
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2001)
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)
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