2-(Trimethylsilyl)ethoxymethyl chloride

CAS No.：76513-69-4

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2-(Trimethylsilyl)ethoxymethyl chloride Basic information

Product Name:	2-(Trimethylsilyl)ethoxymethyl chloride
Synonyms:	SEM-CHLORIDE;SEM-CI;SEM-CL;2-(TRIMETHYLSILYL)ETHOXYMETHYL CHLORIDE;2-(CHLOROMETHOXY)ETHYLTRIMETHYLSILANE;CHLOROMETHYL 2-TRIMETHYLSILYLETHYL ETHER;2-(Trimethylsilyl)ethoxymethyl chloride ,95% [0.1% diisopropylethylamine as stabilizer];2-(triMethylsilyl)ethoxyMethyl chl
CAS:	76513-69-4
MF:	C6H15ClOSi
MW:	166.72
EINECS:	278-483-4
Product Categories:	Aliphatics;Biochemistry;Protection & Derivatization Reagents (for Synthesis);Reagents for Oligosaccharide Synthesis;Si (Classes of Silicon Compounds);Si-(C)4 Compounds;Silicon Compounds (for Synthesis);Synthetic Organic Chemistry
Mol File:	76513-69-4.mol

2-(Trimethylsilyl)ethoxymethyl chloride Chemical Properties

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.	2-8°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
Sensitive	Moisture Sensitive
Hydrolytic Sensitivity	7: reacts slowly with moisture/water
BRN	3587289
InChIKey	BPXKZEMBEZGUAH-UHFFFAOYSA-N
CAS DataBase Reference	76513-69-4(CAS DataBase Reference)

Safety Information

Hazard Codes	C
Risk Statements	10-34
Safety Statements	26-28-36/37/39-45-16
RIDADR	UN 2920 8/PG 2
WGK Germany	3
F	8-10-21
TSCA	No
HazardClass	3.2
PackingGroup	III
HS Code	29319090

MSDS Information

Provider	Language
2-(Trimethylsilyl)ethoxymethyl chloride	English
SigmaAldrich	English
ACROS	English

2-(Trimethylsilyl)ethoxymethyl chloride Usage And Synthesis

Chemical Properties	Colorless to light yellow liqui
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.
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.
Uses	Phenol protecting group in the synthesis of laterifluorones.
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.
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.]

2-(Trimethylsilyl)ethoxymethyl chloride Preparation Products And Raw materials

Raw materials	2-(Trimethylsilyl)ethanol-->1-BROMO-2-CHLOROMETHOXY-ETHANE
Preparation Products	4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-([2-(trimethylsilyl)ethoxy]methyl)-1H-pyrazole

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