2-(Trimethylsilyl)ethoxymethyl chloride

ALDRICH/92749 - ≥95.0% (GC)

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

CAS Number: 76513-69-4
Empirical Formula (Hill Notation): C₆H₁₅ClOSi
Molecular Weight: 166.72
EC Number: 278-483-4
MDL Number: MFCD00009919
Linear Formula: (CH₃)₃SiCH₂CH₂OCH₂Cl
Product Type: Chemical

Catalog Number	PKG Qty.	Price


45-92749-5ML	5 mL	$199.00 1/EA	Add To Favorites
45-92749-25ML	25 mL	$509.00 1/EA	Add To Favorites

Properties
Descriptions
Safety Info.
Basic Data

assay	≥95.0% (GC)
bp	170-172 °C (lit.)
	57-59 °C/8 mmHg (lit.)
density	0.942 g/mL at 25 °C (lit.)
form	liquid
InChI	1S/C6H15ClOSi/c1-9(2,3)5-4-8-6-7/h4-6H2,1-3H3
InChI key	BPXKZEMBEZGUAH-UHFFFAOYSA-N
refractive index	n20/D 1.435 (lit.)
	n20/D 1.436
shipped in	wet ice
SMILES string	C[Si](C)(C)CCOCCl
storage temp.	−20°C

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
Packaging:	5, 25 mL in glass bottle

Symbol	GHS02,GHS05
Signal word	Danger
Hazard statements	H226 - H314
Precautionary statements	P280 - P305 + P351 + P338 - P310
Hazard Codes	C
Risk Statements	10-34
Safety Statements	26-28-36/37/39-45
RIDADR	UN 2920 3(8) / PGII
WGK Germany	WGK 3
Flash Point(F)	114.8 °F - closed cup
Flash Point(C)	46 °C - closed cup

Purity	≥95.0% (GC)
bp	170-172 °C (lit.); 57-59 °C/8 mmHg (lit.)
Density	0.942 g/mL at 25 °C (lit.)
Refractive Index	n20/D 1.435 (lit.); n20/D 1.436
Storage Temp.	−20°C
UNSPSC	12352101

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