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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.)

functional group

chloro
ether

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 4: Flammable liquids
Type 2 petroleums
Hazardous rank III
Water insoluble liquid

JAN Code

92749-VAR:
92749-BULK:
92749-25ML:
92749-5ML:


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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.

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