92749

2-(Trimethylsilyl)ethoxymethyl chloride

≥95.0% (GC)

• Sinônimo(s): (2-Chloromethoxyethyl)trimethylsilane, Chloromethyl 2-trimethylsilylethyl ether, SEM-Cl, SEM-chloride
• Fórmula linear: (CH₃)₃SiCH₂CH₂OCH₂Cl
• Número CAS: 76513-69-4
• Peso molecular: 166.72
• Beilstein: 3587289
• Número CE: 278-483-4
• Número MDL: MFCD00009919
• Código UNSPSC: 12352101
• ID de substância PubChem: 57653488
• NACRES: NA.22

Propriedades

• Nível de qualidade: 100
• Ensaio: ≥95.0% (GC)
• Formulário: liquid
• índice de refração: n20/D 1.435 (lit.); n20/D 1.436
• p.e.: 170-172 °C (lit.); 57-59 °C/8 mmHg (lit.)
• densidade: 0.942 g/mL at 25 °C (lit.)
• grupo funcional: chloro; ether
• Condições de expedição: wet ice
• temperatura de armazenamento: −20°C
• cadeia de caracteres SMILES: C[Si](C)(C)CCOCCl
• InChI: 1S/C6H15ClOSi/c1-9(2,3)5-4-8-6-7/h4-6H2,1-3H3
• chave InChI: BPXKZEMBEZGUAH-UHFFFAOYSA-N

Descrição

Descrição geral

2-(Trimethylsilyl)ethoxymethyl chloride (SEM-Cl) is a widely used reagent for the preparation protection groups for amines, alcohols, phenols, and carboxy groups.[1][2] The nitrogen of amides and sulfonamides groups are also protected by using SEM-Cl reagent.[1]

Aplicação

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.[1] It can also be used in the synthesis of amino acid SEM esters from N-protected amino acids in the presence of lithium carbonate.[3]

Outras notas

Protecting-group reagent for alcohols and other functional groups selectively removable with Bu₄NF [4][5][6]; Protecting group for pyrroles and imidazoles, facilitating selective metalation [7]; Reagent for the introduction of a protected C₁ building block [8]

Informações de segurança

• Pictogramas: GHS02,GHS05
• Palavra indicadora: Danger
• Frases de perigo: H226,H314
• Declarações de precaução: P210 - P233 - P240 - P280 - P303 + P361 + P353 - P305 + P351 + P338
• Classificações de perigo: Flam. Liq. 3 - Skin Corr. 1B
• Código de classe de armazenamento: 3 - Flammable liquids
• Classe de risco de água (WGK): WGK 3
• Ponto de fulgor (°F): 114.8 °F - closed cup
• Ponto de fulgor (°C): 46 °C - closed cup
• Equipamento de proteção individual: Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter