2-(Trimethylsilyl)ethoxymethyl chloride CAS#: 76513-69-4; ChemWhat Code: 1489906

IdentificationPhysical DataSpectra
Route of Synthesis (ROS)Safety and HazardsOther Data

Identification

Product Name2-(Trimethylsilyl)ethoxymethyl chloride
IUPAC Name2-(chloromethoxy)ethyl-trimethylsilane
Molecular StructureStructure of 2-(Trimethylsilyl)ethoxymethyl chloride CAS 76513-69-4
CAS Registry Number 76513-69-4
EINECS Number278-483-4
MDL NumberMFCD00009919
Beilstein Registry Number3587289
Synonyms76513-69-4
2-(Trimethylsilyl)ethoxymethyl chloride
(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-Chloromethyl 2-(trimethylsilyl)ethyl ether
SILANE, [2-(CHLOROMETHOXY)ETHYL]TRIMETHYL-
(2-Chloromethoxyethyl)trimethylsilane
2-(chloromethoxy)ethylsilane
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
EINECS 278-483-4
MFCD00009919
2-(chloromethoxy)ethyl-trimethyl-silane
Chloromethyl 2-trimethylsilylethyl ether
SCHEMBL5579
(CH3)3SiCH2CH2OCH2Cl
trimethylsilylethoxymethychloride
G8Q8Y64LT8
trimethylsilylethoxymethylchloride
DTXSID10227327
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
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
(2-trimethylethylsilylethoxy)methyl chloride
2-(chloromethoxy)ethylsilane
[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
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
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
Molecular FormulaC6H15ClOSi
Molecular Weight166.72
InChIInChI=1S/C6H15ClOSi/c1-9(2,3)5-4-8-6-7/h4-6H2,1-3H3
InChI KeyBPXKZEMBEZGUAH-UHFFFAOYSA-N
Isomeric SMILESC[Si](C)(C)CCOCCl   
Patent Information
Patent IDTitlePublication Date
CN107226814Preparation method for intermediate of Baricitinib2017
US2012/22581SUBSTITUTED FUSED PYRIMIDINE COMPOUNDS, ITS PREPARATION AND USES THEREOF2012

Physical Data

AppearanceColourless to light yellow liquid
Melting Point, °C
57 – 59
Boiling Point, °CPressure (Boiling Point), Torr
57 – 598
Density, g·cm-3Measurement Temperature, °C
1.0525

Spectra

Description (NMR Spectroscopy)Nucleus (NMR Spectroscopy)Solvents (NMR Spectroscopy)Frequency (NMR Spectroscopy), MHz
Spectrum1H300
Spectrum13C
Chemical shifts13Cacetone-d668
Chemical shifts1Hacetone-d6300
1Hacetoacetone-d6300
Chemical shifts1HCDCl3
Chemical shifts13CCDCl3
Description (IR Spectroscopy)Solvent (IR Spectroscopy)
BandsKBr

Route of Synthesis (ROS)

Route of Synthesis (ROS) of 2-(Trimethylsilyl)ethoxymethyl chloride CAS 76513-69-4
Route of Synthesis (ROS) of 2-(Trimethylsilyl)ethoxymethyl chloride CAS 76513-69-4
ConditionsYield
Stage #1: Indole-3-carboxaldehyde With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 1h; Inert atmosphere;
Stage #2: (2-trimethylethylsilylethoxy)methyl chloride In N,N-dimethyl-formamide for 2h;		98%
Stage #1: Indole-3-carboxaldehyde With sodium hydride In N,N-dimethyl-formamide at 0 – 20℃; Inert atmosphere;
Stage #2: (2-trimethylethylsilylethoxy)methyl chloride at 0 – 20℃;

Experimental Procedure
2.4. Typical procedure for the preparation of 1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indole-3-carbaldehydes: synthesis of the 1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indole-3-carbaldehyde
To a stirred suspension of NaH (331 mg, 8.27 mmol, 1.2 equiv.) in DMF anhydrous (5 mL) was added dropwise a solution of 1H-indole-3-carbaldehyde (1.0 g, 6.89 mmol, 1.0 equiv.) dissolved in anhydrous DMF (10.0 mL) at 0°C under argon. The mixture was stirred for 1 hour, warmed to room temperature and stirred until the salt was formed. Then, reaction mixture was cooled to 0°C before adding dropwise SEMCl (1.40 mL, 7.58mmol, 1.1 equiv.), warmed to room temperature and stirred for 10 minutes. After the consumption of the substrate (TLC, n-hexane-EtOAc, 80:20), the reaction was diluted with Et2O, washed with a solution of KHSO4 (10% w/w), a saturated solution of NaHCO3, and brine. The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by chromatography on SiO2 (25-40 μm), eluting with 85/15 (v/v) n-hexane/AcOEt mixture (Rf = 0.22) to obtain 1.85 g (97% yield) of 1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indole-3-carbaldehyde.		97%
With sodium hydride Substitution;85%

Safety and Hazards

Pictogram(s)flamecorrosion
SignalDanger
GHS Hazard StatementsH226 (100%): Flammable liquid and vapor [Warning Flammable liquids]
H314 (97.92%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]
H318 (10.42%): Causes serious eye damage [Danger Serious eye damage/eye irritation]
Precautionary Statement CodesP210, 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
(The corresponding statement to each P-code can be found at the GHS Classification page.)

Other Data

Druglikeness
Lipinski rules component
Molecular Weight166.723
logP2.264
HBA1
HBD0
Matching Lipinski Rules4
Veber rules component
Polar Surface Area (PSA)9.23
Rotatable Bond (RotB)4
Matching Veber Rules2
Use Pattern
2-(Trimethylsilyl)ethoxymethyl chloride CAS 76513-69-4 (SEM-Cl) is an organosilicon compound commonly used as a protecting group in organic synthesis. 
SEM-Cl is frequently used as a protecting group in organic synthesis, particularly for protecting hydroxyl (-OH) and amino (-NH2) groups. The use of protecting groups can prevent these functional groups from undergoing unwanted reactions during the synthesis process, thereby increasing the selectivity and efficiency of the synthesis.
In the synthesis of complex organic molecules, SEM-Cl can be used to temporarily protect certain functional groups. Once other parts of the synthesis are completed, the protecting group can be removed under specific conditions to restore the original functional group.

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