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:
Molecular Weight:
166.72
UNSPSC Code:
12352101
NACRES:
NA.22
PubChem Substance ID:
EC Number:
278-483-4
Beilstein/REAXYS Number:
3587289
MDL number:
Assay:
≥95.0% (GC)
Form:
liquid
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
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
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signalword
Danger
hcodes
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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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)
B.H. Lipshutz et al.
Tetrahedron Letters, 21, 3343-3343 (1980)
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.
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 92749-25ML | 04061833270370 |
| 92749-5ML | 04061837535475 |