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Merck
CN

92749

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:
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

Key Documents

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Product Name

2-(Trimethylsilyl)ethoxymethyl chloride, ≥95.0% (GC)

InChI key

BPXKZEMBEZGUAH-UHFFFAOYSA-N

InChI

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

SMILES string

C[Si](C)(C)CCOCCl

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

Quality Level

100

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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.

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.

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

signalword

Danger

hcodes

H226,H314

Hazard Classifications

Flam. Liq. 3 - Skin Corr. 1B

Storage Class

3 - Flammable liquids

wgk

WGK 3

flash_point_f

114.8 °F - closed cup

flash_point_c

46 °C - closed cup

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

Regulatory Information

危险化学品
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Certificates of Analysis (COA)

Lot/Batch Number
BCCN5804
BCCL4295
BCCM2073
BCCK7352
BCCH3401

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B.H. Lipshutz et al.
Tetrahedron Letters, 30, 7149-7149 (1989)
N. Fujina et al.
Heterocycles, 34, 303-303 (1992)
D. Crich et al.
Synlett, 117-117 (1990)
Decarboxylative arylation of substituted pyrroles N-protected with 2-(trimethylsilyl) ethoxymethyl (SEM).
Figliola C, et al.
Canadian Journal of Chemistry, 999, 1-9 (2018)
2-(Trimethylsilyl) ethoxymethyl Chloride
Earley J and Adams CM
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2001)
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