238902

2-(Trimethylsilyl)ethoxymethyl chloride

technical grade

• 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: 24854351
• NACRES: NA.22

Properties

• grade: technical grade
• Quality Level: 100
• form: liquid
• refractive index: n20/D 1.435 (lit.)
• bp: 170-172 °C (lit.); 57-59 °C/8 mmHg (lit.)
• density: 0.942 g/mL at 25 °C (lit.)
• 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

Learn More at the Professor and Product Portal of Professor Bruce Lipshutz.

Application

Phenol protecting group in the synthesis of laterifluorones.

Used to prepare a SEM-ether which was, in turn, removed with BBr₃ and cyclized to a benzo-oxapane.

Features and Benefits

Convenient hydroxyl-protecting reagent. SEM-ethers are stable over a wide pH range, and can be selectively cleaved with fluoride ion under mild aprotic conditions.

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: Eye Dam. 1 - 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