92749

2-(Trimethylsilyl)ethoxymethyl chloride

≥95.0% (GC)

• Synonym(s): (2-Chloromethoxyethyl)trimethylsilane, Chloromethyl 2-trimethylsilylethyl ether, SEM-Cl, SEM-chloride
• Linear Formula: (CH₃)₃SiCH₂CH₂OCH₂Cl
• CAS Number: 76513-69-4
• Molecular Weight: 166.72
• Beilstein: 3587289
• EC Number: 278-483-4
• MDL number: MFCD00009919
• UNSPSC Code: 12352101
• PubChem Substance ID: 57653488
• NACRES: NA.22

Properties

• 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.)
• 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

Safety Information

• Pictograms: GHS02,GHS05
• Signal Word: Danger
• Hazard Statements: H226,H314
• Precautionary Statements: P210 - P233 - P240 - P280 - P303 + P361 + P353 - P305 + P351 + P338
• 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