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92749

2-(Trimethylsilyl)ethoxymethyl chloride

Name: 2-(Trimethylsilyl)ethoxymethyl chloride
Brand: ALDRICH

≥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:

76513-69-4

Molecular Weight:

166.72

UNSPSC Code:

12352101

NACRES:

NA.22

PubChem Substance ID:

57653488

EC Number:

278-483-4

Beilstein/REAXYS Number:

3587289

MDL number:

MFCD00009919

Assay:

≥95.0% (GC)

Form:

liquid

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Properties

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.)

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

Description

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