Description

2-Chloromethyl 2-(trimethylsilyl)ethyl ether (CAS: 76513-69-4) is a highly versatile organosilicon compound widely used in synthetic organic chemistry. With the molecular formula C₆H₁₅ClOSi, this reagent serves as a critical protecting group for alcohols and amines under the SEM (2-(Trimethylsilyl)ethoxymethyl) protocol. Its stability, reactivity, and ease of deprotection make it indispensable in multistep syntheses, particularly in peptide and nucleoside chemistry. Available in high purity (≥95% by GC), this product is stabilized with diisopropylethylamine to ensure long-term storage stability. Ideal for researchers requiring precise and reproducible results in complex molecular architectures.

Properties

• CAS Number: 76513-69-4
• Complexity: 69.9
• IUPAC Name: 2-(chloromethoxy)ethyl-trimethyl-silane
• InChI: InChI=1S/C6H15ClOSi/c1-9(2,3)5-4-8-6-7/h4-6H2,1-3H3
• InChI Key: BPXKZEMBEZGUAH-UHFFFAOYSA-N
• Exact Mass: 166.0580693
• Molecular Formula: C6H15ClOSi
• Molecular Weight: 166.72
• SMILES: C[Si](C)(C)CCOCCl
• Topological: 9.2
• Monoisotopic Mass: 166.0580693
• Synonyms: 76513-69-4, 2-(Trimethylsilyl)ethoxymethyl chloride, 2-Chloromethyl 2-(trimethylsilyl)ethyl ether, SILANE, [2-(CHLOROMETHOXY)ETHYL]TRIMETHYL-, EINECS 278-483-4, DTXSID10227327, Silane, (2-(chloromethoxy)ethyl)trimethyl-, DTXCID10149818, Silane, 2-(chloromethoxy)ethyltrimethyl-, 278-483-4, (2-(CHLOROMETHOXY)ETHYL)TRIMETHYLSILANE, 2-(Trimethylsilyl)ethoxymethylchloride, SEM-chloride, [2-(chloromethoxy)ethyl]trimethylsilane, 2-(chloromethoxy)ethyl-trimethylsilane, SEM-Cl, 2-(Chloromethoxy)ethyltrimethylsilane, SEM chloride, (2-Chloromethoxyethyl)trimethylsilane, [2-(chloromethoxy)ethyl](trimethyl)silane, Chloromethyl 2-(trimethylsilyl)ethyl ether, (2-(chloromethoxy)ethyl]trimethylsilane, {2-(chloromethoxy)ethyl}trimethylsilane, (2-(chloromethoxy)ethyl)-trimethylsilane, [2-(chloromethoxy)ethyl]-trimethylsilane, SEMCl, (2-(chloromethoxy)ethyl)(trimethyl)silane, {2-[(chloromethyl)oxy]ethyl)(trimethyl)silane, {2-[(chloromethyl)oxy]ethyl}(trimethyl)silane, MFCD00009919, 2-(chloromethoxy)ethyl-trimethyl-silane, Chloromethyl 2-trimethylsilylethyl ether, SCHEMBL5579, 2-(Trimethylsilyl)ethoxymethyl Chloride (SEM-Cl), (CH3)3SiCH2CH2OCH2Cl, trimethylsilylethoxymethychloride, G8Q8Y64LT8, trimethylsilylethoxymethylchloride, trimethylsilylethoxymethyl chloride, 2-chloromethoxyethyltrimethylsilane, 2-trimethysilylethoxymethyl chloride, BCP07277, CS-D0859, (trimethylsilyl)ethoxymethyl chloride, 2-(Trimethylsilyl)ethyl hypochlorite, 2-Trimethylsilylethoxymethyl chloride, BBL102768, chloromethyl trimethylsilylethyl ether, STL556574, trimethylsilylethyl chloromethyl ether, 2-trimethylsilyl-ethoxymethyl chloride, 2-trimethylsilylethoxy-methyl chloride, 2-trimethylsilylethyoxymethyl chloride, (2-chloromethoxy-ethyl)trimethylsilane, (2-chloromethoxyethyl)-trimethylsilane, 2-(chloromethoxy)ethyltrimethyl silane, 2-(Chloromethoxyethyl)trimethyl silane, 2-(tnmethylsilyl)ethoxymethyl chloride, 2-(trimethylsily)ethoxymethyl chloride, 2-(trimethylsilyl)ethoxymethy chloride, 2-(Trimethysilyl)ethoxymethyl chloride, 2-trimethylsilanyl-ethoxymethylchloride, 2-trimethylsilanylethoxymethyl chloride, AKOS005259763, chloro-2-(trimethylsilyl)ethoxymethane, (2-trimethylsilylethoxy)methyl chloride, 2-(trimethylsilyl)-ethoxymethylchloride, FC10778, FS-3821, (2-chloromethoxy-ethyl)-trimethylsilane, (2-Chloromethoxy-ethyl)trimethyl-silane, (2-chloromethoxyethyl)-trimethyl-silane, 2-(chloromethoxy)ethyl(trimethyl)silane, 2-(trimethylsilyl)ethoxylmethyl chloride, 2-(trimethysilyl)ethoxy methyl chloride, (2-(chloromethoxy)-ethyl)trimethylsilane, (2-(Chloromethoxy)ethyl) trimethylsilane, (2-(chloromethoxy)ethyl)trimethyl-silane, (2-Chloromethoxy-ethyl) trimethyl-silane, (2-chloromethoxy-ethyl)-trimethyl-silane, (2-trimethylsilylethyl)oxymethyl chloride, [-(trimethylsilyl)ethoxy]methyl chloride, [2-(chloromethoxyl)ethyl]trimethylsilane, 2- (trimethylsilyl)ethoxymethyl chloride, 2-(chloromethoxy)-ethyl-trimethyl-silane, 2-(trimethyl-silyl)ethoxymethyl chloride, 2-(trimethylsilanyl)ethoxymethyl chloride, 2-(trimethylsilyl) ethoxymethyl chloride, 2-(trimethylsilyl)ethoxy methyl chloride, 2-(trimethylsilyl)ethoxy-methyl chloride, [2-(trimethylsilyl)ethoxy]methyl chloride, 2-(trimethylsilyl) ethoxy methyl chloride, BP-21202, [beta-(Trimethylsilyl)ethoxy]methylchloride, (2-trimethylethylsilylethoxy)methyl chloride, [2-(chloromethoxy)ethyl] (trimethyl)silane, [2-(chloromethoxy)ethyl]-(trimethyl)silane, 1-(chloromethoxy)-2-(trimethylsilyl)ethane, 2-(trimethyl-silanyl)-ethoxymethyl chloride, DB-005799, DB-312931, [2-(Chloromethoxy)ethyl]trimethylsilane 90%, [2-[(Chloromethyl)oxy]ethyl]trimethylsilane, [beta-(Trimethylsilyl)ethoxy]methyl chloride, 90% (stabilized with Diisopropylethylamine), NS00120487, EN300-86442, S03978, [[beta-(Trimethylsilyl)ethyl]oxy]methyl chloride, {2-[(chloromethyl)oxy]ethyl} (trimethyl)silane, 2-(TRIMETHYLSILYL)-ETHOXYMETHYL CHLORIDE, Hypochlorous acid, 2-(trimethylsilyl)ethyl ester, 2-(Trimethylsilyl)ethoxymethyl chloride, >=95.0% (GC), 2-(Trimethylsilyl)ethoxymethyl chloride, technical grade, F0001-1949, 2-(Chloromethoxyethyl)trimethyl silane – stabilized with ca. 0.1% Diisopropylethylamine, 2-(TRIMETHYLSILYL)ETHOXYMETHYL CHLORIDE (STABILIZED WITH DIISOPROPYLETHYLAMINE), 2-(Trimethylsilyl)Ethoxymethyl Chloride 90%, Stab. With 0.1% N,N-Diisopropylethylamine, Aksci Technical Grade2-(Trimethylsilyl)Ethoxymethyl Chloride 90%, Stab. With 0.1% N,N-Diisopropylethylamine, Chloromethyl 2-trimethylsilylethyl ether;SEM-Cl;2-(Trimethylsilyl)ethoxymethyl chloride;SEM-chloride

This compound is primarily used as a protecting group reagent for hydroxyl and amino functionalities in organic synthesis. It offers excellent stability under acidic and basic conditions, making it suitable for multi-step reactions. Commonly applied in peptide chemistry and nucleoside synthesis, it facilitates selective deprotection without affecting other sensitive groups. Its compatibility with Grignard reactions and organolithium reagents further extends its utility in pharmaceutical research.

Safety and Hazards

GHS Hazard Statements

• H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]
• H314 (98%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]
• H318 (10.2%): Causes serious eye damage [Danger Serious eye damage/eye irritation]

Precautionary Statements

• P210, P233, P240, P241, P242, P243, P260, P264, P264+P265, P280, P301+P330+P331, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P317, P321, P363, P370+P378, P403+P235, P405, and P501

Hazard Classes and Categories

• Flam. Liq. 3 (100%)
• Skin Corr. 1B (98%)
• Eye Dam. 1 (10.2%)

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