ChemicalBook CAS DataBase List 76513-69-4

76513-69-4

Name	2-(Trimethylsilyl)ethoxymethyl chloride
CAS	76513-69-4
EINECS(EC#)	278-483-4
Molecular Formula	C6H15ClOSi
MDL Number	MFCD00009919
Molecular Weight	166.72
MOL File	76513-69-4.mol

Synonyms

2-(CHLOROMETHOXY)ETHYLTRIMETHYLSILANE 2-(TRIMETHYLSILYL)ETHOXYMETHYL CHLORIDE CHLOROMETHYL 2-TRIMETHYLSILYLETHYL ETHER SEM-CHLORIDE SEM-CI SEM-CL 2-chloromethyl 2-(trimethylsilyl)ethyl ether 2-(Trimethylsilyl)ethoxymethyl chloride, technical grade 2-(TRIMETHYSILYL)-ETHOXYMETHYL CHLORIDE 2-(Trimethylsilyl)ethoxymethylchloride,stabilized,tech. 2-(Trimethylsilyl)ethoxymethyl chloride, tech., stabilized, 90% 2-ChloroethoxyMethyltrimethylsilane -(trimethysilyl)-ethoxymethylchloride Silane, 2-(chloromethoxy)ethyltrimethyl- 2-(Trimethylsilyl)ethoxymethyl Chloride (SEM-Cl) 2-(TRIMETHYLSILYL)ETHOXYMETHYLCHLORIDE , STABILIZED WITH IPR2MEN {2-[(chloromethyl)oxy]ethyl}(trimethyl)silane 2-(Chloromethoxy)ethyltrimethylsilane (stabilized with Diisopropylethylamine) (2-Chloromethoxyethyl)trimethylsilane, Chloromethyl 2-trimethylsilylethyl ether, SEM-chloride, SEM-Cl 2-(Trimethylsilyl)ethoxymethyl chloride, 90%, tech, stabilized

Chemical Properties

Appearance	Colorless to light yellow liqui
Boiling point	170-172 °C (lit.) 57-59 °C/8 mmHg (lit.)
density	0.942 g/mL at 25 °C(lit.)
refractive index	n20/D 1.435(lit.)
Fp	116 °F
storage temp.	−20°C
solubility	Sol most organic solvents (pentane, CH2Cl2, Et2O, THF, DMF, DMPU, HMPA)
form	Liquid
color	Clear colorless
Specific Gravity	0.95
Water Solubility	decomposes
Hydrolytic Sensitivity	7: reacts slowly with moisture/water
Sensitive	Moisture Sensitive
BRN	3587289
Stability:	Unstable in Solution
InChI	1S/C6H15ClOSi/c1-9(2,3)5-4-8-6-7/h4-6H2,1-3H3
InChIKey	BPXKZEMBEZGUAH-UHFFFAOYSA-N
SMILES	C[Si](C)(C)CCOCCl
CAS DataBase Reference	76513-69-4(CAS DataBase Reference)

Safety Data

Symbol(GHS)	GHS02,GHS05
Signal word	Danger
Hazard statements	H226-H314
Precautionary statements	P280-P305+P351+P338-P310
Hazard Codes	C
Risk Statements	R10:Flammable. R34:Causes burns. less more
Safety Statements	S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . S28:After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer) . S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . S16:Keep away from sources of ignition-No smoking . less more
RIDADR	UN 2920 8/PG 2
WGK Germany	3
F	8-10-21
TSCA	No
REACH Registrations	Inactive
HazardClass	3.2
PackingGroup	III
HS Code	29319090
Storage Class	3 - Flammable liquids
Hazard Classifications	Flam. Liq. 3 Skin Corr. 1B

Hazard Information

Chemical Properties

Colorless to light yellow liqui

Physical properties

bp 57–59 °C/8 mmHg; d 0.942 g cm?3.

Uses

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.

General Description

2-(Trimethylsilyl)ethoxymethyl chloride (SEM-Cl) is a widely used reagent for the preparation protection groups for amines, alcohols, phenols, and carboxy groups. The nitrogen of amides and sulfonamides groups are also protected by using SEM-Cl reagent.

Synthesis

75-77-4

1462-35-7

76513-69-4

Step 4: Take a small amount of intermediate reagent and place it in the reactor, heat to reflux and maintain reflux for 4 hours. After completion of the reaction, cool to 20°C and slowly add trimethylchlorosilane dropwise. During the dropwise addition, the temperature of the solution was gradually increased. Step 5: At the end of the reaction, desorption operation was carried out, controlling the temperature of the depressurized reactor not to exceed 40°C. The residual system residue was dissolved to form a viscous substance, and ethanol was added slowly until no bubbles were generated, and the waste was disposed of. Finally, the solution obtained by desolventization is distilled to collect 2-(trimethylsilyl)ethoxymethyl chloride with a purity of more than 99%.

Purification Methods

Dissolve SEMCl in pentane, dry it (MgSO4), evaporate and distil the residual oil in a vacuum. Stabilise it with 10ppm of diisopropylamine. Store it under N2 in a sealed container in a refrigerator. [Lipshutz & Pegram Tetrahedron Lett 21 3343 1980.]

References

[1] Patent: CN103408576, 2016, B. Location in patent: Paragraph 0020; 0021; 0025
[2] Patent: CN108409776, 2018, A. Location in patent: Page/Page column 5-7

Material Safety Data Sheet(MSDS)

Spectrum Detail

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