2-(Trimethylsilyl)ethoxymethyl chloride CAS 76513-69-4
Introduction：Basic information about 2-(Trimethylsilyl)ethoxymethyl chloride CAS 76513-69-4, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
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 | n |
| 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 |
| Sensitive | Moisture Sensitive |
| Hydrolytic Sensitivity | 7: reacts slowly with moisture/water |
| 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 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 |
| Storage Class | 3 - Flammable liquids |
| Hazard Classifications | Flam. Liq. 3 Skin Corr. 1B |
| 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 formaldehydeequivalent; 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 |
2-(Trimethylsilyl)ethoxymethyl chloride Preparation Products And Raw materials
| Raw materials | 2-(Trimethylsilyl)ethanol-->1-BROMO-2-CHLOROMETHOXY-ETHANE-->Formaldehyde-->Chlorotrimethylsilane |
| 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]- |
