2-(Trimethylsilyl)ethoxymethyl chloride

Base Information

• Chemical Name: 2-(Trimethylsilyl)ethoxymethyl chloride
• CAS No.: 76513-69-4
• Molecular Formula: C6H15ClOSi
• Molecular Weight: 166.723
• Hs Code.: 29319090
• European Community (EC) Number: 278-483-4
• DSSTox Substance ID: DTXSID10227327
• Nikkaji Number: J319.335G
• Wikipedia: 2-(Trimethylsilyl)ethoxymethyl_chloride
• Wikidata: Q72514453
• Mol file: 76513-69-4.mol

Synonyms:76513-69-4;2-(Trimethylsilyl)ethoxymethyl chloride;(2-(CHLOROMETHOXY)ETHYL)TRIMETHYLSILANE;2-(Trimethylsilyl)ethoxymethylchloride;SEM-chloride;2-(chloromethoxy)ethyl-trimethylsilane;2-(Chloromethoxy)ethyltrimethylsilane;[2-(chloromethoxy)ethyl]trimethylsilane;2-Chloromethyl 2-(trimethylsilyl)ethyl ether;(2-Chloromethoxyethyl)trimethylsilane;SILANE, [2-(CHLOROMETHOXY)ETHYL]TRIMETHYL-;[2-(chloromethoxy)ethyl](trimethyl)silane;EINECS 278-483-4;(2-(chloromethoxy)ethyl]trimethylsilane;{2-(chloromethoxy)ethyl}trimethylsilane;(2-(chloromethoxy)ethyl)-trimethylsilane;[2-(chloromethoxy)ethyl]-trimethylsilane;SEMCl;(2-(chloromethoxy)ethyl)(trimethyl)silane;SEM-Cl;{2-[(chloromethyl)oxy]ethyl)(trimethyl)silane;{2-[(chloromethyl)oxy]ethyl}(trimethyl)silane;SEM chloride;MFCD00009919;2-(chloromethoxy)ethyl-trimethyl-silane;Chloromethyl 2-trimethylsilylethyl ether;SCHEMBL5579;(CH3)3SiCH2CH2OCH2Cl;trimethylsilylethoxymethychloride;trimethylsilylethoxymethylchloride;DTXSID10227327;trimethylsilylethoxymethyl chloride;2-chloromethoxyethyltrimethylsilane;BPXKZEMBEZGUAH-UHFFFAOYSA-N;2-trimethysilylethoxymethyl chloride;BCP07277;CS-D0859;(trimethylsilyl)ethoxymethyl chloride;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;AM84124;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;Chloromethyl 2-(trimethylsilyl)ethyl ether;[2-(chloromethoxy)ethyl] (trimethyl)silane;[2-(chloromethoxy)ethyl]-(trimethyl)silane;1-(chloromethoxy)-2-(trimethylsilyl)ethane;2-(trimethyl-silanyl)-ethoxymethyl chloride;[beta-(Trimethylsilyl)ethoxy]methyl chloride;FT-0608986;EN300-86442;S03978;{2-[(chloromethyl)oxy]ethyl} (trimethyl)silane;2-(TRIMETHYLSILYL)-ETHOXYMETHYL CHLORIDE;A838732;2-(Trimethylsilyl)ethoxymethyl chloride, >=95.0% (GC);2-(Trimethylsilyl)ethoxymethyl chloride, technical grade;F0001-1949;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

Chemical Property of 2-(Trimethylsilyl)ethoxymethyl chloride

Chemical Property:

• Appearance/Colour: Colorless to light yellow liquid
• Vapor Pressure: 1.12mmHg at 25°C
• Refractive Index: n20/D 1.435(lit.)
• Boiling Point: 182.1 °C at 760 mmHg
• Flash Point: 46.7 °C
• PSA: 9.23000
• Density: 0.92 g/cm³
• LogP: 2.53750
• Storage Temp.: −20°C
• Sensitive.: Moisture Sensitive
• Solubility.: Sol most organic solvents (pentane, CH2Cl2, Et2O, THF, DMF, DMPU, HMPA)
• Water Solubility.: decomposes
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 166.0580693
• Heavy Atom Count: 9
• Complexity: 69.9

Purity/Quality:

99% ^*data from raw suppliers

2-(Trimethylsilyl)ethoxymethyl chloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 10-34
• Safety Statements: 26-28-36/37/39-45-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C[Si](C)(C)CCOCCl
• Physical properties: bp 57–59 °C/8 mmHg; d 0.942 g cm?3.
• Uses: 2-(Chloromethoxy)ethyltrimethylsilane is used in the preparation of SEM [2-(trimethylsilyl)ethoxy]methyl]-ethers. It serves as a phenol protecting group in the synthesis of laterifluorones. Further, it reacts with 1H-imidazole to prepare 1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole. 2-(Trimethylsilyl)ethoxymethyl Chloride is a reagent used in the protection of alcohols, secondary aryl amines, and imidazole, indole, and pyrrole nitrogens;electrophilic formaldehyde equivalent; acyl anion equivalent,used in One-carbon Homologations, Cyclizations etc. Phenol protecting group in the synthesis of laterifluorones.

Technology Process of 2-(Trimethylsilyl)ethoxymethyl chloride

There total 2 articles about 2-(Trimethylsilyl)ethoxymethyl chloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

chloro-trimethyl-silane (75-77-4) + 1-bromo-2-(chloromethoxy)ethane (1462-35-7) → (2-trimethylethylsilylethoxy)methyl chloride (76513-69-4)

Guidance literature:

1-bromo-2-(chloromethoxy)ethane; With magnesium; for 4h; Reflux;

chloro-trimethyl-silane; at 20 ℃; Reagent/catalyst;

Reference yield: 90.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 2-(Trimethylsilyl)ethanol (2916-68-9) → (2-trimethylethylsilylethoxy)methyl chloride (76513-69-4)

Guidance literature:

With hydrogenchloride; for 0.5h;

DOI:10.1021/ja00385a029

Reference yield: 90.0%

(2-trimethylethylsilylethoxy)methyl chloride (76513-69-4) + 3-iodo-1H-pyrazole (4522-35-4) → 4-iodo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazole (220299-49-0)

Guidance literature:

3-iodo-1H-pyrazole; With sodium hydride; In tetrahydrofuran; at 0 ℃; for 0.5h; Inert atmosphere;

(2-trimethylethylsilylethoxy)methyl chloride; In tetrahydrofuran; at 20 ℃; for 16h; Inert atmosphere;

DOI:10.1021/acs.orglett.7b02944

upstream raw materials:

formaldehyd

2-(Trimethylsilyl)ethanol

chloro-trimethyl-silane

1-bromo-2-(chloromethoxy)ethane

Downstream raw materials:

1-[(2-(trimethylsilyl)ethoxy)methyl]-1H-pyrazole

1-(2-Trimethylsilylethoxymethyl)-1H-benzoimidazole

Phenyl-acetic acid 2-trimethylsilanyl-ethoxymethyl ester

3-<<2-(trimethylsilyl)ethoxy>methyl>-2-phenylimidazole

Refernces

• 1、 -. "Synthetic method of 2-(trimethylsilyl)ethoxymethyl chloride". Page/Page column 5-7. . Retrieved 2018/09/11.
• 2、 -. "METHOD OF PRODUCING SILYLALKOXYMETHYL HALIDE". Page/Page column 6; 7. . Retrieved 2008/06/13.