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| | 2-(Trimethylsilyl)ethoxymethyl chloride Basic information |
| | 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 | | Specific Gravity | 0.95 | | color | Clear colorless | | Water Solubility | decomposes | | Hydrolytic Sensitivity | 7: reacts slowly with moisture/water | | Sensitive | Moisture Sensitive | | BRN | 3587289 | | Stability: | Unstable in Solution | | InChIKey | BPXKZEMBEZGUAH-UHFFFAOYSA-N | | CAS DataBase Reference | 76513-69-4(CAS DataBase Reference) |
| 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 |
| | 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 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-->5H-Pyrrolo[3,2-d]pyrimidine, 2-chloro-5-[[2-(trimethylsilyl)ethoxy]methyl]--->1-((2-(Trimethylsilyl)Ethoxy)Methyl)-1H-Benzo[D]Imidazole-->2-((2-(triMethylsilyl)ethoxy)Methoxy)propanoic acid-->1H-Imidazole, 2-bromo-1-[[2-(trimethylsilyl)ethoxy]methyl]--->4-iodo-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine-->1H-Pyrazole, 4-iodo-1-[[2-(triMethylsilyl)ethoxy]Methyl]- |
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