[2-(chloromethoxy)ethyl]trimethylsilane

• ChemBase ID: 150670
• Molecular Formular: C6H15ClOSi
• Molecular Mass: 166.7212
• Monoisotopic Mass: 166.05806931
• SMILES: C[Si](C)(C)CCOCCl
• Canonical SMILES: ClCOCC[Si](C)(C)C
• InChI: InChI=1S/C6H15ClOSi/c1-9(2,3)5-4-8-6-7/h4-6H2,1-3H3
• InChIKey: BPXKZEMBEZGUAH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [2-(chloromethoxy)ethyl]trimethylsilane
• IUPAC Traditional name: [2-(chloromethoxy)ethyl]trimethylsilane
• Synonyms: SEM-Cl; (2-Chloromethoxyethyl)trimethylsilane; Chloromethyl 2-trimethylsilylethyl ether; SEM-chloride; 2-(Trimethylsilyl)ethoxymethyl chloride; (2-(Chloromethoxy)ethyl)trimethylsilane; [2-(chloromethoxy)ethyl]trimethylsilane; 2-(Trimethylsilyl)ethoxymethyl chloride; (2-氯甲氧基乙基)三甲基硅烷; SEM-氯化物; 氯甲基三甲基硅乙基醚; 2-(三甲基硅烷基)乙氧甲基氯

Database IDs

• CAS Number: 76513-69-4
• EC Number: 278-483-4
• MDL Number: MFCD00009919
• Beilstein Number: 3587289
• PubChem SID: 24889710; 162244831; 24854351
• PubChem CID: 2724271

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 2.5247
• LogD (pH = 7.4): 2.5247
• Log P: 2.5247
• Molar Refractivity: 38.0825 cm^3
• Polarizability: 17.253086 Å^3
• Polar Surface Area: 9.23 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 170-172 °C(lit.); 57-59 °C/8 mmHg(lit.)
• Flash Point: 114.8 °F; 46 °C
• Density: 0.942 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.435(lit.); n20/D 1.436
• Hydrophobicity(logP): 2.575

Safety Information

• European Hazard Symbols: Corrosive (C)
• UN Number: 2920
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2
• Risk Statements: 10-34
• Safety Statements: 26-28-36/37/39-45
• GHS Pictograms: GHS02; GHS05
• GHS Signal Word: Danger
• GHS Hazard statements: H226-H314
• GHS Precautionary statements: P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2920 8/PG 2
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95.0% (GC); 95%; 95+%; 97%; 98%
• Grade: technical grade
• Contains: 10 ppm diisopropylethylamine as stabilizer
• Shipped in: wet ice
• Linear Formula: (CH3)3SiCH2CH2OCH2Cl

DETAILS

Sigma Aldrich - 92749

Other Notes
Protecting-group reagent for alcohols and other functional groups selectively removable with Bu4NF 1,2,3; Protecting group for pyrroles and imidazoles, facilitating selective metalation 4; Reagent for the introduction of a protected C1 building block 5
Packaging
5, 25 mL in glass bottle

Sigma Aldrich - 238902

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Application
Phenol protecting group in the synthesis of laterifluorones.1
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.2,3
Packaging
1, 5, 25, 100 g in glass bottle