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.)

Flash point:

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

Stability:

Unstable in Solution

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

• Language:English Provider:2-(Trimethylsilyl)ethoxymethyl chloride
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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.

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(76513-69-4)Related Product Information

• (Trifluoromethyl)trimethylsilane
• Choline chloride
• Chlorodimethylphenylsilane
• Chloromethyltrimethylsilane
• Ethoxytrimethylsilane
• Ethyl acetate
• Ammonium chloride
• C8E3
• Lithium bis(trimethylsilyl)amide
• Methyltrimethoxysilane
• Diethoxydimethylsilane
• tert-Butyldimethylsilyl chloride
• Ethylbenzene
• Polyvinyl chloride
• Acetyl chloride
• Trimethylsilylacetylene
• Sodium chloride
• CHLOROMETHYLPHENYLSILANE