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2-(Trimethylsilyl)ethoxymethyl chloride

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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
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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)
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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
8-10-21
TSCA 
No
HazardClass 
3.2
PackingGroup 
III
HS Code 
29319090

MSDS

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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.]

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